Last week, Kevin and I participated in our first ever car rally with Mike Ward Automotive for their annual autumn leaves driving event in the Rockies. I feel so fortunate to join this awesome community. We enjoyed some awe-inspiring drives with stops in mountain towns including Berthoud Pass, Independence Pass, Steamboat Springs, Aspen, and Vail.

There’s a lot going on in the world, and I’m closely managing my information diet these days to strike a balance between being informed vs. being overwhelmed.

In the 30 minutes I allow myself to read the news each day, I’m following events in Ukraine/Russia, Florida, climate change, and local crime in Colorado with deep concern and compassion for human suffering. It’s really painful to read the news, and I’m starting to think more tactically about what I can do to get involved. I’ve said “I’m not political” outwardly for a long time, but I think that’s changing soon.

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Investing Thoughts

On the other hand, I’m following the mid-term elections and unwinding of a decade of money creation in the US with morbid curiosity.

Inflation

I figure since we have no choice but to live through this part of the cycle, I better learn something from it, and to better understand our last dramatic inflationary period I started reading Michael Darby’s The International Transmission of Inflation (1984) last night. We’ve come a long way from hand-building models on Mark II and Mark III computers.

I’m grateful we were able to refinance our house when rates were at their lowest, and I’m looking at our other debt exposure to make sure we’re being smart. Kevin and I got married right before the 07/08 collapse, and we’ve been reflecting on what we learned from some of the top-of-market decisions we made last time. My hope is that we can make only new mistakes. The main topic of conversation is around how much more (if any) risk to take, how to collateralize it, and whether to pause development on the land we bought next door to our house since financing for construction loans has gotten very expensive and fixed rate options are basically not a thing at all right now.

Private Companies & Funds

At least in the face of all this volatility, we’ve continued to invest in startups and funds, and achieved our goal of deploying ~5% of our net worth this year.

Me: “Are you investing?”

Him: “If we had a fund I would. I’m super illiquid rn”

Me: “just deployed remainder of my fun money for the year, so I’m in the same boat”

So what investments closed out my dry powder for the year?

This week I put up my first capital call into the latest Heavybit fund (developer tools), and invested $100K in the Series A of a space tech transportation company (join my syndicate to see the deal details and participate in the SPV I’m leading). This is my first syndicate on AngelList, and wrangling investors has provided an education in LP communication that reminds me of the Mattermark party-round days. Kicking it off als led to some inbound interest about me raising a fund.

Although I’ve raised millions on AngelList for my startups, I haven’t been very actively on the platform as an investor. Now that I’m dipping my toe in, I can see there are benefits to having regular deals happening so investors get more and more familiar with what I’m into. So far, I’ve learned that running one-off SPVs is often time-consuming because it requires continuous cultivation of LP relationships an investor brand. I’m not ready to pull the trigger on this fund business quite yet, but I’ve got a few potential partners in mind and I’m definitely factoring this into my thought process as I start to rough draft my 2023 goals.

Public Companies

It’s probably time to circle back to these, but it’s been nice to have a break from tracking the market on a daily basis. I continue to hold my long concentrated positions in Twilio and GitLab, and I believe Twilio in particularly seems massively oversold (-78% in the past 12 months) while GitLab remains significantly below its IPO price. I’m looking forward to getting myself back into a position cash-flow wise where I can be a buyer in this market, but right now I am in look but don’t touch with these two and a handful of other names including Cloudflare, Palantir, Crowdstrike, Snowflake, and Porsche (why not?).

It’s a great time to read deeply and learn, but I’m not ready to transact or go back to building any kind of tracking portfolio.

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Around Town in Denver

I went to my first two NFL games in Colorado, where we watched Broncos fans boo the home team… so that was interesting. It was an ugly win both games, but we got there! I’m a long way from being converted to a Broncos fan from my loyal Seahawks fandom, but it was fun to explore Mile High Stadium and I even managed to bruise my hand and lose my voice in my enthusiasm.

The real highlight was getting to hang out with former Mattermark team member Karlie (3rd from right) who recently relocated to Denver from Chicago. One of the many things I love about having lived more years is how wonderful people fro one chapter of life drift back to me again in another, through the natural course of events. I’ve got my O.G. cat loving space pants SoulCycle buddy back!

Eating Well

We’ve been enjoying the bounty of the season in our local Denver restaurants, especially fresh peaches and late season corn.

If you’re headed through Denver anytime soon, here are a few spots I recommend:

• Brunch: Bacon Social House in Sunnyside, Le Bilboquet in Cherry Creek North, Root Down in Highland, and of course Snooze (multiple locations)
• Chill Dinner: Lucina Eatery in Park Hill, The Greenwich in RiNo, Benzina in Park Hill and The Fifth String in Highland
• Fancy Dinner: The Wolf’s Tailor in Sunnyside, Restaurant Olivia in Wash(ington) Park, Bistro Barbes in Park Hill, and Beckon in RiNo

I’m pretty thrilled to see that people are reading my tweets and eating at these awesome spots!

Kevin “KMac” Damaso @project_kmac

Dinner @ Bistro Barbès in Denver Thanks to @DanielleMorrill for the recommendation, Chef John is a gem of a human

1:58 AM ? Sep 29, 20226Likes1Retweet

All these places are amazing and you should try them. But as I write this I can see I need to branch out to different neighborhoods more often, and I’m ready to up my brunch game in particular. I’m fairly adventurous, but it’s easy to get into a pattern. If you have Denver restaurant recommendations, please add them in the comments!

I also asked for recommendations for our upcoming trip to Seattle, and I want to eat everywhere mentioned in the replies.

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What I’m Reading

My Goodreads is as meticulously up-to-date as ever, and I hope you’ll join more than 700 people who follow me there for interesting updates in your books feed!

Theme: Social Status & Class

• The Protestant Establishment: Aristocracy & Caste in America by E. Digby Baltzell (1964)
• Status: Why Is It Everywhere? Why Does It Matter? by Cecilia L. Ridgeway (2019)
• Wanting: The Power of Mimetic Desire in Everyday Life by Luke Burgis (2021) who also has an excellent Substack publication
• The Status Game: On Social Position and How We Use It by Will Storr (2021)
• Virtue Signaling: Essays on Darwinian Politics and Free Speech by Geoffrey Miller (2019)

Theme: Parenting

• Good Inside: A Guide to Becoming the Parent You Want to Be by Dr. Becky Kennedy (2022)
• The Blank Slate: The Modern Denial of Human Nature by Steven Pinker (2003)
• What We Owe the Future by William MacAskill (2022)

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Intermittent Fasting Update

Week 5 is done! This week I logged a new PR for hours in the fat burning “zone” (between hour 16 and 24 of a fast). It feels like I’m getting the hang of this. My biggest challenge is definitely dealing with the moodiness inspired by my physical feelings of hunger in the final hours of each fast.

My goal is to achieve ~16 hours per week in this zone and sustain that, which can happen simply by sticking to a simple 18:6 schedule (18 hours fasting, followed by a 6 hour feeding window) with a couple extra fasting hours tacked on when I feel like its going well and I can stand to wait a little longer.

I haven’t yet ventured beyond a 24 hour fast yet, but now that I have the all-clear from my doctor and some guidelines around where the limits are (refuel with healthy nutrient rich foods, don’t pass out, drink a LOT of water and pee nearly clear throughout) I’m hoping to experiment with ketosis soon to get some other health benefits besides weight loss. Fortunately, I did a blood panel in August and all my biomarkers are looking good, so I can focus on making this change while I’m otherwise healthy.

In addition to intermittent fasting, I’ve enrolled in a 12-week weight management course with Forward Health and got a referral for CBT (Cognitive Behavioral Therapy) with a specialist focused specifically on this area. I am hopeful that I can make changes that are long-lasting (so that I won’t ever need to buy a new wardrobe of clothes again!), maintain good mental health along the way, and stay of the “obese” clinical category from now on (only ~5 pounds to go!) to reduce my exposure to the health risks associated with obesity.

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Go Broncos!

What a lovely break I’ve enjoyed from writing for the eyes of others. Thank you for the space. This morning I’m enjoying a break from the heat wave we’ve been having here in Denver, with temperatures down in the mid 50s. The dogs love it, and so do I!

Investing

My most active investment, my own startup Firstparty, celebrated the milestone of getting its first paying customer over the summer and we are still working on getting to product/market fit. It’s been nearly a decade since I was hands on with this phase of startup building, and it is a humbling journey and test of patience to be sure.

On the private company side, I’m working with a couple long-time startup founder friends on a frontier tech deal that we will be syndicating through an SPV on AngelList. To maintain confidentiality for the company I won’t be sharing details via this newsletter, but if you’d like to sign up to be notified when there is more information available you can join my LP network on AngelList.

Not much happened for me in the public markets over the summer, and I’m still long on my concentrated positions in Twilio and GitLab. I’m burned out my my “learning portfolio” approach to researching companies, and need to come up with something new that I find more engaging.

Leadership Coaching

I took about 6 weeks off, and I’m feeling refreshed. After a lot of reflection, I’ve realized that I was chronically underestimating how much emotional work I do as background processing (outside of session time) when I have active client engagements. To improve my recovery and boundaries, I’ve raised my rates and I’m coaching from mid-September to early December, and then taking another break. I don’t currently have open slots available, but you can reach out to me at danielle@morrillcoaching.com if you would like to get those email updates.

Travel

We did a lot of US travel by car this summer including our first visit to Amangiri in Utah and road-trips to Aspen, Glenwood Springs, and Gateway. We got back to California for the first time since early pandemic days, with a week in Napa around July 4th and a week in Monterey for Car Week.

We also made it up to Washington State (where we’re both from) to see family in Snohomish and Kingston, and attend a beautiful wedding in Friday Harbor.

We’ll probably have 5-6 more 90+ degree days here in Denver before we head into what is usually a fairly short but very beautiful Autumn, so I’m looking forward to several days of mountain town exploring and fall leaves peeping drives.

Health

I continue to be less of a try-hard when it comes to my goals for the year. In fact, I’m pretty sure I’m on pace to miss all of them except for the health ones. I’ve gotten into intermittent fasting and I’m averaging ~2 lbs. a week of weight loss. If I could end this year back at what I weighed right before the pandemic began, that would be amazing. As to the rest, I’m just focused on making little bits of progress every day. We found out Kevin’s vasectomy reversal didn’t work, so we’re still deciding what our next moves are there and getting more curious about both surrogacy and adoption (reading list to come in a future update).

Around the House

Day-to-day life has been pretty sweet since I last wrote to you in May, with lots of growing, cooking, and eating of my garden vegetables. I’m thinking we probably have 2-3 more weeks of growing season and then it will be time to harvest and preserve whatever we haven’t already eaten. I’m planning to make a lot of salsa.

We now have preliminary designs for the pool house, and received our permit to remove the house that is currently on the land. Demo begins on Tuesday!

Life Improvement Moves

• Sold my learning portfolio so I could stop checking Robinhood
• Set up Sanebox to digest my emails for processing 3x per week
• Removed all apps from my phone’s home screen and made it grayscale
• Hired a personal assistant to help me with life chores I procrastinate on
• Bought an Eightsleep mattress cover to improve my sleep quality (if use my link you’ll get $200 off if you buy a mattress or mattress cover)
• Started intermittent fasting with the Zero app
• Signed up for a primary care provider through Forward
• Set up Jumbo Security to archive my tweets and monitor for password leaks

Ah, Fall. I can almost smell the fresh pencil shavings (do kids even use No 2 pencils anymore?) and after this final heat wave passes in Denver, I’m looking forward to cozy sweaters and mountain drives to see the changing autumn colors.

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A quick note on communicate channels: I’ve stopped using Facebook and Instagram. If you are one of the people I unfriended, please know it’s not personal. After trying some half-measures, it was the only effective way to stop wasting so much time perusing and performing. You can still find me through this newsletter and on Twitter.

Sometimes y’all get too damn serious… let’s play!

We spent the past week and a half in Bozeman, Montana supporting dear friends as they make a major life move to buy a homestead there. You can see Emo and Taco loved it!

Checking in on 2022 Goals

I added a couple new coaching clients while on the trip and have achieved my 2022 goal of billing $10K/month for that business. Rather than fast forwarding to set a 2023 goal, I’ve decided to stop striving around growing Morrill Coaching LLC for a bit and just settle into these new client relationships.

My focus now is on:

• Baby making (quite fun!)
• Product/Market fit for Firstparty (quite challenging!)
• Baseline health (10K steps, 8+ hours of sleep, eating plants)

It’s funny, now that we can conceive I’m feeling a lot less urgency about it. Anyone else have that experience?

I turned 37 a few weeks ago, and I’d be lying if I said I felt the tick of a biological clock. I don’t feel it. I just feel really peaceful in my marriage and home life, and if we add a baby to the mix I know it will be an awesome adventure. And if we don’t, that’s okay too. I will just have to get more dogs.

In terms of other people’s timelines, Kevin just turned 44, and I think he is a little more aware of what it will mean to be an “old Dad” since he had one. He’s fit and healthy as a horse now, but the fact is he will be in his mid-60s by the time our kids graduate high school. There are also my parents, who are in their mid-60s now and hopefully will live for a long long time to come. They just want more grandkids, and who can blame them? Our kids will already be the youngest among 5 other cousins ranging age 14 to 2, and unless my little sister decides to have more I am probably going to be the last one in this generation having kiddos.

Kevin and I are celebrating 15 years of marriage in August, and I feel peaceful.

Nesting Much?

I am excited to share that we bought the house next door to ours in Denver!

We’re working with the original architect and builder of our house (which was constructed in 2005) to turn the lot into a pool, patio, garden, and guest house. I find it calming having our home as our central shared project during all this chaotic market noise, and it makes it easy to be long on all our other investments. I feel fortunate that we found a diversification move that is so life enriching.

Kevin has agreed to take the lead on project management, and I’m sure you’ll see some house updates (and I’m sure some dark humor about budgets and plans and all that) in the coming months. For now, we’re in the queue with the city of Denver for permits and demolition is the next step. I’m thinking about how we can take some brick from the original house and set it aside to build the pizza oven or something else, as small nod to the past.

Market What How Now?

Emotionally, I’m barely noticing the shock waves from the financial markets. Maybe it’s because I never internalized the massive run up of the past few years as real gains? I just updated my “CFO of the household” spreadsheet, and it was pretty wild to plug in a number ~75% lower than in late December for my stock holdings account balance.

As most of you already know, I have two heavily concentrated positions in Twilio and GitLab that come from my time working for these two companies. I’ve come to realize that the way I hold startup stock in my mind is different, and perhaps something that others would benefit from knowing about. I look at it as rainy day upside, not as compensation and not as “real” money until I sell. Even though it is liquid post-IPO I still look at is as an option, and in the case of Twilio where proceeds are QSBS qualified I am even more circumspect. As those who are Super Following me on Twitter know, I’ve been buying more of both.

Here’s the latest result of my learning portfolio as of Friday’s close:

Kevin and I drove back to Denver from a visit with friends in Bozeman, Montana on Wednesday and during that 700 mile trek we had to time talk over things a bit re: the market. “I’m thinking through what’s the truly worst case scenario for us,” I told him, “To really be in trouble, we’d have to be fundamentally wrong about software and what it can do for the world.” Obviously there are some other geopolitical SHTF scenarios that are also worst case, but that’s on the downside. On the upside, my theory is that power law value creation in the future will come primarily from psychological goods rather than physical goods (bits vs. atoms).

I see no evidence this is fundamentally breaking. If anything, we are still in the early innings. For those who want to increase their own conviction, I highly recommend reading Future Shock and Revolutionary Wealth by Alvin Toffler

I also “initiated research” (sounds so official doesn’t it?) on a number of companies, which means I bought 1 share and I am planning to read a lot more about them, write up an exec summary, and decide if I want to build a bigger position in the coming months/years:

Thinking Like a Gardener

I’ve been cultivating seedlings since March, and yesterday I started planting them. Of course, I managed to dump a whole tray of marigolds onto the ground and exclaimed reflexively “No, my babies!”

Most of them were fine, and I got them in the ground. Plants are surprisingly resilient, even when they’re tiny. However, this morning I went out to survey how the peppers I put in did overnight, and its clear there are several that have shriveled up and are not going to make it. Experienced gardeners know transplanting is traumatic, and we product more seedlings than we need because we’ll be removing dead plants and subbing in new ones until everything takes.

I feel the sunk cost of the months of cultivating when tossing the tiny plant remains into the compost with a silent Marie Kondo style “thank you”.

I do worry whether there are people suffering in silence, because despite all the bravado to “fail fast” its still quite taboo to be open about losses and failures. When things go badly, the message among the startup and crypto set seems to be caveat emptor. Toughen up kid. I had to take a significant break from Twitter with the most recent crypto swirl, as there is too much grave dancing for my taste.

This weekend, I encourage you all to think about how you can spread the message of long-term thinking, cultivation, and agency. As my friend, investor, and investing partner Chip Hazard shares — thinking like a gardener is called for.

Read the full Twitter thread here.

Chip Hazard @chazard

Having chatted about this with a lot of founders this week, a final somewhat obvious point. Focus on what you can control: team, customers, products, spending, investors, etc and not on what you can’t control. In other words, less doom scrolling and more gardening!

Chip Hazard @chazard

Some thoughts while gardening this weekend and seeing this grim chart and stats. I was a venture investor across both major corrections, which were quite different. ???? https://t.co/rbzVV3kaY56:37 PM ? May 13, 20225Likes1Retweet

What I’m Reading Lately

• Virtue Hoarder: The Case Against the Professional Management Class by Catherine Liu
• The Ruthless Elimination of Hurry by John Ortberg
• The Arc by Tory Henwood Hoen
• Complexity: The Emerging Science at the Edge of Order and Chaos by M. Mitchell Waldrop
• Independent People by Halldor Laxness
• Start Where You Are by Pema Chodron
• The Ruthless Elimination of Hurry by John Mark Comer
• Work Clean by Dan Charnas
• The Burnout Society by Byung-Chul Han

I’ve been on a tear with reading, thanks to an incredible deluge of high quality recommendations from my Twitter followers. To get a taste of that they provided in response to my prompts, check out these threads…

Elle Morrill ???? ? @DanielleMorrill

What is the most transformative and/or useful book on being a good Christian? aside from the Bible of course5:22 PM ? May 14, 202221Likes2Retweets

Elle Morrill ???? ? @DanielleMorrill

What is the best book you’ve ever read concerning dignity?5:16 PM ? May 14, 202213Likes1Retweet

As always, I’d love to hear your recommendations on these prompts and anything else you think would tickle my noggin’

Have a great week everyone!

Wow, another year in the books! I came into December ready to be done with “school” (Hudson) and feeling pretty spent after a year full of endings and beginnings, including riotously intense periods of effort and intentional idling and reclaiming of time. I’ve established boundaries and simplified my work down to ~20 hours per week, and I’m loving the time freedom.

In 2021 I continued to stretch my working identity beyond startups founder and employee, dipping my toe deeper into public service with a Governor-appointed board position and also making a move toward professional coaching as an ongoing vocation.

I also made the transition back to startup founder after a 4 year break that saw me take a year of sabbatical, lead an internal startup (which was spun out and backed by GV), and join the senior management team of a multi-billion dollar startup with a lot more experience and perspective than last time around (Twilio). During that time, I had my first opportunity to report to a professional CMO and got an up close and personal look at the largest Sales & Marketing machine I’ve had the opportunity to contribute to so far.

For this new startup, I have identified my sweet spot as reporting to the CEO, instead of being one. I’ve grown a lot as a leader through all my experiences, and I’m so excited to bring this next iteration of myself as founder to Firstparty alongside Jonathan. For my next act, I’m going to stretch into the CTO role for the first time.

I could not have completed these milestones without the love, help and support of my husband, my friends, my boss, my colleagues, my investing partners, my learning group, and my community both online and IRL.

I’ve also had the privilege of retaining a wonderful supporting staff (housekeeper, gardener, personal assistant) and a suite of software solutions (Calendly, Reclaim.ai, Zoom, Linear, Sanebox, Audible) who make the day-to-day of living and working a-sync and fully remote across two businesses possible. Thank you!

2021 Milestones

• Turned 36
• 4 years living in Denver
• Started my startup CEO coaching business
• Joined the board of Colorado Statewide Internet Portal Authority (SIPA)
• Wrapped up my time at Gitlab shortly before the IPO
• Started a new developer tools startup with a long-time friend, where I am cofounder and CTO
• Completed the Hudson Coach Certification program
• Kevin and I got our first super car!
• Finished reading 107 books

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2021 Lamborghini Huracán EVO Spyder in Blu Cepheus

2022 Forecast

• Get pregnant (I’ve changed my tune about having kids)
• Spend more time with my nephews and nieces and extended family
• House remodel Part 1
• Run the coaching business (Objective: reach $100K annual revenue)
• Run the startup (Objective: Product Market Fit)
• Finish reading 200 books (I have 352 in “Currently Reading”)
• Start NO new businesses in 2022
  

On Having Kids

TL;DR We’re going to attempt to make some little humans to nurture and love. Their existence will bring more meaning, joy, play, adventure, novelty, and entropy into our lives. I can’t wait!

In June 2019 I wrote a post about my decision to be child-free, and now just over 2 years later, after a second dog and during an ongoing global pandemic, I changed my mind. As usual, the process was a combination of effort and good fortune. Here’s a brief rundown:

I got a lot closer to my husband during the pandemic, after 10+ years of hectic startup life. Looking back its wild to remember that I returned from my honeymoon in 2007 and dove straight into my first startup job. Even after a year of sabbatical in 2018, only the pandemic really slowed me down enough to let myself invest deeply in our the long term vision for our relationship and life together. I love you Kevin.

Working at GitLab radically changed my understand of what work/life integration could look like, and modeled for me a different vision of my professional future. It inspired me with a real-life example of the kind of workplace I will create for others as a business owner. Fundamentally the emphasis is on results delivered, not hours worked.

I got a lot more dialed into what brings meaning and joy to my life. Turns out, its more than startups! I’m finding though my work as a coach and public servant that I derive a great deal of meaning and enjoyment from bringing my passion for leadership and talent development to new contexts. I’m much more comfortable with interdependence, ambiguity, and patience for waiting at the “middle places” in life.

I accepted my own finite lifetime as a real thing, and started living accordingly. Accepting this fact enabled me recognize that the choice to have kids or not is a one-way door decision, and could potentially be a source of deep regret for me in the future. I used to think I would regret having kids, because I saw it as trading off my ambitions and time. Now that my ambitions have been (and continue to be) realized, and I have a system for managing my time and boundaries, I’ve effectively mitigated those downside risks. I’ve also accepted that living a life with no regrets is simply not possible, and set that perfectionism aside.

I made a life-changing amount of money, and I’m going to use it make parenting easier wherever possible. This is an incredible privilege, and I plan to deploy it against whatever barriers we come up against.

I’m sure I left something out, and it really feels like this short post hardly begins to express the thought and care that has gone into changing our minds. Ultimately, this is a deeply personal choice, which I expect will completely change my life and rock my world, in ways that I can read about but are clearly something one has to experience first-hand to really understand. I look forward to being humbled, greatly.

It’s the day before Thanksgiving, which is traditionally when I start to work on my annual reflection and goal setting process. New Year’s Eve is my favorite holiday, because it is on of the few that encourages introspection completely devoid of religion or other dogma. We make it meaningful in our own personal ways, and for me the punctuation gives a much needed sense of time passing to a life that rarely unfolds linearly.

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Over the years, I’ve refined my annual process while also letting it take up more time of the year. This let’s me do my tasks at a more lazy and luxurious pace. I also take a lot of time off this time of year, which is fairly easy with Thanksgiving and Christmas going on. I think I have perhaps 9 or 10 more business days I need to attend to in 2020.

In line with the Thanksgiving holiday, my process begins by taking inventory of the year. Overall, my purpose is to become a more complex Human being through experiences, choices, and actions that I take in response to my environment and to my goals.

Thematically, 2020 definitely shifted my decisions about where to focus. I had expected it to be a year of deepening friendships and making new ones in Denver, joining a club or two to take up some sports I loved as a kid but rarely do anymore (Swimming, tennis, horseback riding), joining a local choir, trying more new restaurants in the burgeoning food scene. Sadly, many of those things became difficult to do in March with the pandemic, but instead I filled my life with other adventures like cooking, meditation, and of course epic road trips all over the United States.

As my friend Jonathan assessed when we were talking about my guilt around feeling like I’d had a pretty good 2020 all in all, despite the pandemic, “you’re good at making yourself happy” and I agree. Sometimes I think it took being very unhappy for awhile after I sold my company to really figure this out, but actually I think I knew how to make myself happy when I was a kid… I just needed to remember how.

To take inventory, I find it helpful to flip back through my calendar, journal, camera roll, GoodReads, and fitness tracking on my phone and build a chronological list of the year. I like to include anything I know I had strong feelings about, positive or negative.

January

• Started my A Ticker A Day stocks newsletter
• Lot’s of Seahawks football on TV
• Taco was spayed, and had a rough recovery that kind of scared me
• Photographed the orchids at Denver Botanic Gardens with Kevin
• My friend Michelle came to visit from San Francisco, and we went to Steamboat Springs so I could learn to ski for the first time ever!
• Got serious about prepping for a potential lockdown, thanks to my friends (and investment in) ThePrepared.com
• Finished 7 books

February

• 9 days in Hawaii with my parents
• Helicopter tour of Oahu
• Tour of Kahumana organic farm and dinner there
• Deep sea fishing we caught a 60 pound ahi tuna (and I was sea sick — rare for me — because we were out in a storm most of the time)
• Outdoor massage and stargazing session with an astronomer
• More snow!
• Hosted game night at home with friends
• Las Vegas with friends for a birthday celebration
• Experienced the amazing hammam spa at the Cosmopolitan!
• Finally saw the Beatles Love show and it lived up to the hype
• 1 year anniversary working at GitLab
• Started transitioning leadership of Meltano (internal startup)
• Finished 6 books

March

• March 5th – first 2 Covid-19 cases are reported in Colorado
• Last manicure/pedicure before lockdown
• Last dinner out before lockdown, at Barolo Grill — we were sitting at the bar when everyone heard about Tom Hanks getting sick, and it all became truly real that this was happening
• March 16th — Lockdown begins in Colorado
• Started a 6 month tour of duty as interim Senior Director of Corporate Marketing at GitLab, while its leader was on parental leave
• Started reporting to a CMO for the first time in my career
• More snow!
• First “Zoom Shabbat”
• Kickoff for CovidLine Colorado volunteer engineering project to get free and anonymous telemedicine and Covid-19 testing to Coloradans during the initial surge (which was anticipated to peak April 14th)
• More snow!
• Finished 3 books

April

• Frantically working to get CovidLine launched, but we do with radio interviews and locals news and a lot of government red tape
• First “Zoom double date”
• More snow!
• My birthday, still in lockdown
• F-16s fly over Denver and the Front Range in honor of first responders
• First “Zoom happy hour”
• Massive burrito prep cooking adventure (and blog post)
• April 27th — Lockdown ends, “Safer at Home” order remains (Masks, distancing, reduced office space capacity, no indoor dining etc.)
• Finished 4 books

May

• Recurring extended family Sunday Zoom calls begin (20-30 people)
• First “Birthday Party Zoom”
• First “Zoom brunch”
• Kevin’s birthday
• Celebrated 1 full year of Taco in our lives!
• Formation of my 2nd team at work, Growth Marketing (which would become my permanent team after the interim role ended) — I’m leading the largest indirect org size (~50) I’ve had since peak Mattermark (~70) and enjoying it
• First “Zoom poker night”
• Dyed my hair hot pink (again)
• Built my raised beds and started planting the summer crop (tomatoes, peppers, herbs, lettuce, blueberries, strawberries, chard, squash)
• Watched the SpaceX launch live
• First time scheduling a Peloton ride at the same time as a friend
• Finished 3 books
• Hit a new high month for average daily steps: 11,609

June

• More planting!
• Kicked off our internal Minorities in Tech mentorship at work
• First “Zoom wine tasting”
• Led my first virtual offsite with my Corporate Marketing team
• First outdoor restaurant meal in the time of Covid, at The Wolf’s Tailor
• First BYO outdoor socially distanced dinner at someone else’s house
• Received a sourdough starter!
• Kicked off planning for our Enterprise site about.gitlab.com/enterprise
• Finished 10 books

July

• Our friend Max came to visit from San Francisco
• New water heater installed!
• Celebrate our 1st full year in our house
• Trip to Grand Lake, CO to stay at Anya and Andy’s cabin in RMNP (which very sadly burned down in the East Troublesome Fire)
• First time seeing a moose in the wild
• Kevin did his first astrophotography with the lens I got him for Xmas
• First haircut all year!
• Led my first virtual team building day for my Growth Marketing team
• Finished 3 books

August

• 2 week road trip to Jackson Hole, WY and Ennis, MO to spend time with my parents (who met us in the middle from the Seattle, WA area)
• First time fly fishing — and I caught some fish!
• First time in Grand Teton and Yellowstone National Park
• Wildfires start getting really bad in Colorado
• Started transitioning out of my interim leadership role
• First virtual YC Alumni Demo Day
• Celebrated our 13th wedding anniversary with a long weekend in Vail and an awesome hike in White River National with our new boots
• Harvesting the garden begins
• Finished 4 books

September

• Camped with our friends John and Carlotta near Nederland, CO
• Slept in a camper van for the first time!
• Sept 6th — Harvest goes intense, as it is expected to freeze, and we have to hit the road to California in a few days
• Sept 9th — First snow of the season! (It’s still technically Summer)
• Taught the Mattermark case study at Harvard Business School (via Zoom) for the last time
• Packed up the dogs and started driving West
• Saw our friends Sarah and Patrick for dinner in Salt Lake City, UT
• Stayed the night in Truckee, and sang a socially distanced rendition of ”Sweet Caroline” with a bunch of strangers at the Ritz Carlton
• Arrived in California amidst the wildfire smoke, and stayed in Sonoma for 2 weeks in the most amazing quarantine pod house with many dear friends. It was great to see Samiur, Tess, Andy, Kate, Carrie, Fawaz, Joseph, Brett, Lindsey, Jes, Max,. We cooked, swam, and there was even a piñata.
• Got to meet our dear friends newest baby, and see their new home
• Went to The French Laundry for the first time!
• Massive pastry hauls from Bouchon and Model Bakery
• Wine tastings at Quintessa and VJB
• Got a rooftop cargo box for the car
• Decided to combine this road trip with another we had planned to Arizona, instead of going home, and headed South to Pasadena
• Arrived at our beautiful Joshua Tree, CA Airbnb for 10 days
• Met up with Colorado friends Tyler and Kat for a hike to an oasis at 29 Palms, and got to reconnect after many months apart
• Finished 3 books
• Hit a new high for average monthly active calories per day: 939 cal

October

• The most gorgeous super moon I’ve ever seen
• Friends Jonathan and Regan drove from Scottsdale to stay with us in Joshua Tree. Much cooking, cigars, and relaxing ensued
• Hot tubbing in the middle of the desert at sunset
• Drove to Scottsdale with Jonathan and Regan, and checked into an Airbnb for an entire month with a fenced yard and a pool
• Led my first virtual offsite for my Growth Marketing team
• Oona pizza oven delivered! SO MANY PIZZAS
• Seahawks are back on TV
• Saw D’Laina and her niece for dinner at Fellow Osteria
• The Local Donut, Cafe Monarch, and FnB
• Andy and Kate arrived in Scottsdale from San Francisco to complete our quarantine pod, and there were many puppy butt wiggles of joy
• We took a couple days away from the house (a staycation from our vacation LOL) to stay at the Four Seasons at Troon with the dogs, and we got in an awesome hike to the top of Pinnacle Peak.
• Finished 4 books

November

• 5 days in a beautiful New Mexico Airbnb with Andy and Kate (in self-imposed lockdown) playing board games and trying to ignore the election news coverage
• Biden wins the election!
• Drove home to Colorado with Andy and Kate to settle into our quarantine pod household as the Covid-19 numbers aren’t looking good and we are only awaiting federal aid to do another lockdown
• Happy to be back after 10 weeks on the road!
• Finished 1 books (so far)…
• On pace for a new high month for average daily steps: 13,003

I’ve been re-reading financial independence classic “Your Money or Your Life” and it struck me that the exercise where you calculate you “effective hourly wage” after including all work-related expenses (commute, clothes, etc.) is probably one that many people could benefit from doing during this pandemic. I say this because many people during COVID-19, who have been fortunate enough to keep their jobs, have been forced into remote work situations. As a result they’re not commuting each day, eating lunch out of the house, dressing up in work appropriate attire, or doing many of the other things that would normally be required.

In order to do this analysis I’ve created some assumptions about the person and the life changes they are seeing:

• Lives in California, at tax rate of 30% of gross salary
• Makes $100K annual salary, before taxes
• Spouse does not work
• Works 40 hours per week
• Has 2 weeks of paid vacation and 2 weeks of sick days
• Used to commute 45 minutes each way, 5 days a week (6.5 hours total)
• Commuted by car with $400/month payment, using 1 $50 tank of gas per week
• Paid $100/month for car insurance
• Spent $15/day for lunch + $5/day afternoon coffee at the corner deli/cafe
• Spent $300/week for after school care for 2 kids from 3 – 6pm
• Spends $2K/year for work-related clothes and any dry cleaning
• Spends $50 each week on after work food/drinks with colleagues 

Calculating the Effective Hourly Rate

The simple math to calculate our hourly pay says we take $100K and divide it by 48 working weeks, and then divide that by 40 hours per week = $52.08/hour

This simple math is misleading, because it doesn’t take into account all the unpaid time and unreimbursed expenses that are involved in the lifestyle of a commuting worker. To create a more accurate picture, we can calculate as follows:

$100K salary – 30% Taxes ($30K) – Yearly Expenses ($14.4K afterschool care + $4.8K car payment + $2.4K gas + $4.8K on food + $1.2K car insurance +$2K clothes / dry cleaning + $2.4K after work food/drink) = $38K effective annual income

Now divide this by 1,920 working hours (48 weeks at 40 hours per week) = $19.79/hour

And we still haven’t added in the 312 unpaid hours spent on commuting, bringing us to $42.8K divided by (1,920 working hours +312 commuting hours) = $17.03/hour effective hourly rate

This is how the math works out, and why someone who has finally broken through to making that elusive status symbol of “six figures” can still be struggling to get by with less than $20/hour of effective real hourly wages after taxes and work-related expenses. 

Given the general recommendation to spend 30-50% of gross salary on housing, this person might feel spending $30K – $50K on rent/mortgage ($2,500 – $4,200 per month) makes sense, especially for a family of 4 needing a 3 bedroom place within a 45 minute drive to the office. At the low end of housing cost, this leaves ~$1,000/month to cover all discretionary spending (food, Internet, cell phones, healthcare,home and car repairs, etc) and on the high end the family is now spending more than they make simply to put a roof over their heads. It is likely that the spouse, if there is one, will have to take on at least part time work to make this situation sustainable.

How the Numbers Change for Remote Workers

Now let’s look at the effective hourly wage for the remote worker who does not commute or own a car, needs no after school care for the kids, does not by specialized clothes for the office costuming, and saves $10/day by needing just $5 for their lunch meal and afternoon coffee at home. They are also reimbursed by the company for their high speed Internet service, and their calculation looks like this:

$100K salary – 30% Taxes ($30K) – Yearly Expenses ($1.2K on food) + Reimbursements ($1.2K high speed Internet) = $70K effective annual income

They also do not commute, so we don’t have to add in those extra hours spent on the road. $70K divided by (40 hours x 48 weeks) = $36.46/hour effective hourly rate

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Wow. From $17.03/hour to $36.46/hour. The switch to working remote has more than doubled this person’s effective hourly rate. 

Obviously your mileage may vary, and you might include or exclude different variables for your own calculation, but it is clear the move to remote work confers major benefits on workers. 

This post doesn’t even begin to dive into the benefits to companies, like not having to lease commercial real estate and manage physical spaces, but that is widely covered elsewhere. If you’re considering making remote work a permanent part of your life, possibly combined with a move to a lower cost of living place with more favorable tax rates, this is something to keep in mind.

Despite living in an unpredictable world filled with death during the COVID pandemic, I’ve been finding a lot of joy lately in my personal projects.

On the public facing side of things, I have:

• Led a team of volunteer software engineers to help Clinica Colorado launch CovidLine, a Twilio-based IVR and call routing solution that provides multi-lingual symptom screening and free telehealth doctor visits for the uninsured and undocumented in Colorado.
• Started a public equity investing newsletter where I publicly share my decision-making process, which includes a mission to evaluate every company underlying the Vanguard Total Stock Market Index Fund (VTSAX) one company at a time.
• Started a free online cooking class newsletter focused on making the foods I’m passionate about accessible to anyone who wants to try.

On the home front, my inner life development continues and if you follow me on social media you might be getting glimpses of some of these projects:

• Self-reliance, prepping, and cultivating some homesteading skills including growing some of my own pizza toppings. (I was even quoted at the end of this long-form piece on “Silicon Valley Preppers” in the New York Times featuring my friends at ThePrepared.com)
• Journaling and reading extensively around grief. As I processed the end of Mattermark over the past couple year, I’ve realized that loss brought up a lot of old wounds that didn’t receive the attention and tenderness they needed to heal. I’m working to give that to myself now, accept my anger at the sense of abandonment I felt at the time, and reframe those stories as the broader tragedies they were (a teen suicide, a friend’s drug overdose and subsequent months in a coma) without centering on myself and my pain.
• Upping my impeccability level when it comes to all manner of cyclical and entropic life processes like chores, household management, personal finance, self care, hygiene and exercise. They all involve compounding and require long-term thinking, and I have room for improvement in connecting my day-to-day actions with my longer term vision for my life.
• Staying in touch with friends through texts, calls, Zoom double dates and other channels, but also working harder to notice the truth of how close we really are (or aren’t), accepting that, and modifying my expectations and engagement model accordingly. I have found a mobile app called Fabriq extremely helpful for this.
• Continuing to read extensively, though I am significantly behind track for my goal of finishing 200 books this year with 30 completed so far.

And of course, my journey as a home chef continues…

For more food pics, make sure to follow me on Instagram!

The average 60-something today has ~$195K in their 401(k) retirement account. What if you could make one lifestyle change, which would cost you about 2 hours of meal prep every 40 days (~18 hours per year), and would in turn bring your $15/lunch* habit into < $2 per meal? If you invested the savings each year for 32 years (assuming you’re 35 like me, and retirement age is 67) at an average return of 5% compounding each year, you’d have ~$400,000 in additional retirement money at the end of that time.

See the math in this spreadsheet

I realize this isn’t the only reason to do meal prep, but it’s a pretty strong argument for making incremental changes to any habit of convenience. You can do similar calculations for other categories of discretionary spending, like ordering a $5 latte at coffee shops versus making coffee at home, using ride-sharing versus public transportation and walking, and many more habits which are ultimately optional choices we each make about how to spend. For me, looking at these analyses (even when I splurge and choose the more expensive option) really drives home the power of habits to shape outcomes. On such a long timeline it can be difficult to keep what matters most in focus.

Even if you don’t put the money into investments, with the benefit of compounding returns to get you to the full $400K, this is still $160K of direct savings that can be re-allocated to other things you value you more in life than what you ate for lunch today.

This kind of frugal thinking is a cornerstone of the book “Your Money or Your Life”, and whether you’re interested in financial independence or just stuck at home with some time on your hands, these burritos are delicious.

Making Delicious < $2 Steak Burritos

For this recipe, I’ll propose one meal plan so you know exactly what the ingredients are, what the nutrition facts are, and how to put it all together. From here, you can adjust the flavors and macros using vegetables, spices, or a different/more protein for a variety of options, while still staying below the $2 mark.

View the shopping list as a spreadsheet in Google Sheets

I’ve also done a bit of research to break down the nutrition facts of the underlying ingredients in this recipe, to give you a sense of how this performs on macros (fat, carbs, protein) as part of a balanced diet:

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Bringing It All Together

Saturday night before bed: Coat the steak in salt, pepper and spices (paprika, cumin and oregano is good mix) and place in a slow cooker on low for 10 hours (or sous vide at 135 degrees Fahrenheit) overnight.

Sunday morning after breakfast: Remove the steak from the slow cooker or sous vide and shred with two forks or dice into small pieces and set aside to cool. Dice the white onions. Get out the other ingredients and set up an assembly line of on the kitchen table, starting with your pop-up foil.

Place two sheets of foil on the table side-by-side overlapping a couple inches. Lay a tortilla on the foil and apply a thin coat of olive oil (so it won’t stick to the foil when reheated later) and flip over, oil side down on the foil.

Put your driest ingredients in first, to avoid sogginess. The green chili salsa should be the last thing you put in.

Roll it up, and freeze it right away!

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Reheating the Burritos

We’ve wrapped them in foil, so the microwave isn’t an option unless you completely unwrap. For the best flavor, remove a burrito from the freezer and put it into the fridge the night before to thaw or remove it from the freezer in the morning and put it out on the counter to thaw. Preheat the oven to 350 Fahrenheit, and bake for ~1 hour.

The spices and salsa should make the burrito flavorful and moist enough on its own (the raw onions and black beans will steam in the oven), but if you want to make the meal feel a bit fancier garnish with hot sauce, sour cream, limes, salsa, diced jalapeños or even an egg over-easy. Enjoy!

P.S. Going Beyond Burritos

Am I seriously suggesting you eat a burrito for lunch every day for the next 32 years? Well, yes… but also no. One of the biggest challenges to saving money is that frugality is often boring and low status. You might get made fun of for brining a bag lunch to work, but the odds that you will be hanging out with the people you work with in retirement (or even 2 years from now) is low. How much do you actually care?

There are lots of lunch meals you can enjoy for $2 or less that will give you the macros you need. One of my favorites is good old PB&J.

Check out my previous spreadsheet trying to construct < $10 day meal plan that felt yummy and not restrictive here for more ideas.

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Not everyone spends $15 on lunch, but I am basing this off of my own spending while living and working in downtown San Francisco. Some example lunch menus include SOMA Eats, Uno Dos Tacos, and Deli Board.

In 2015, Sam Altman wrote a post titled “Bubble Talk” which lamented the “boring reading” of ongoing press coverage of a bubble in tech valuations, and laid out 3 scenarios he believed would be true by January 1, 2020. To win, Sam has to be right on all three propositions laid out in the post and reviewed in detail below. Sam also invited a VC to take the other side of the bet and Michael de la Maza obliged. The loser will donate $100,000 to a charity of the winner’s choice.

Proposition 1: On January 1st, 2020, the top 6 US companies at http://fortune.com/2015/01/22/the-age-of-unicorns/ (Uber, Palantir, Airbnb, Dropbox, Pinterest, and SpaceX) s will be worth at least $200B in aggregate (from just over $100B in 2015).

Outcome: Not true. The group is collectively worth $30-40B less than $200B, based on publicly reported valuations of private companies and market caps of publicly traded companies.

• Uber = $50.73B Market Cap on Jan. 1, 2020
• Pinterest = $10.41B Market Cap on Jan. 1, 2020
• Dropbox = $7.44B Market Cap on Jan. 1, 2020
• SpaceX = $33.3B private valuation as of May 31, 2019
• Palantir = $20-30B private valuation as of September 2019
• Airbnb = $35B private valuation as of March 2019

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Proposition 2: On January 1^st, 2020, Stripe, Zenefits, Instacart, Mixpanel, Teespring, Optimizely, Coinbase, Docker, and Weebly will be worth at least $27B in aggregate (from just under $9B in 2015).

Outcome: True.

• Stripe alone is valued at $35B as of September 2019

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Proposition 3: The current YC Winter 2015 batch—currently worth something that rounds down to $0—will be worth at least $3B on Jan 1^st, 2020.

Outcome: True.

• GitLab* = $2.75B private valuation as of September 2019
• Razorpay = $450M private valuation as of June 2019
• Atomwise = $150M private valuation as of March 2018
• Chariot = acquired by Ford for $65M

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*Disclosure: I work for GitLab.

In December 2017 my husband, myself, and the remaining cadre of Mattermarkers who remained moved to Denver as renters and “short-timers”. Given how we started out, I didn’t put odds on staying long. We started out fresh from California in the middle of winter, as part of an acquisition capping off a long M&A process that had left me pretty burned out. We hadn’t planned to move, but it was what we needed to do to close the deal so we did it. Alighting on a new city in the midst of the holiday season, we didn’t have our support network built up over the past 10 years (basically my entire adult life) in the Bay Area, let alone the right clothes to weather the initial shock of change.

After spending years building something that’s no longer yours, especially if as in my case you have nothing (at least economically) to show for it, can raise questions about whether it was worth building at all. I spent 5.5 years, from early 2012 to mid 2018, on the Referly/Mattermark/FullContact rollercoaster with an average annual salary of $120K and net negative personal savings rate. In the sale of Mattermark, the purchase price did not clear the amount invested by preferred shareholders and common stock (including all the founders and employees) was wiped out. There was no success fee for completing the deal, just my honor and self esteem + a job offer at the acquirer with a relocation bonus.

I’m not complaining (and doing the deal was ultimately my choice and the best option available to the company), just laying it out in a bit more detail because sometimes I think people try to leave things vague to create an aura of mystery when founders have these types of exits. Despite all the work I’d done to separate my identity from my role as startup CEO, I felt quite shitty about this outcome… and it took a lot longer to work through those feelings than I could have predicted.

Where Am I?

Initially, we lived out of an Airbnb in Washington Park with our 4 month old puppy (Emo) while scouting for a pet-friendly rental in the neighborhood, but ultimately ended up finding a brand new duplex in Cherry Creek North renting for less than our portion of our former 3 bedroom apartment with roommates in San Francisco.

Moving into this tony old neighborhood of Denver was funny, mostly because we constantly felt like the youngest people around. After starting to feel “old” among our eternally 20-something tech startup peers in San Francisco, the average age of 65 was refreshing. Older Denverites of relatively good health are super active with their dogs, their gardens, and myriad outdoor sports and we met a lot of friendly people very quickly. Even at -1F (New Years Day) we relished the walkability of our 16-block shopping district and the mostly sunny climate with 2-4 inches of snow every week or two.

I started learning about the neighborhood’s history, and discovered it was founded as the township of Harman in the 1880s by Edwin P. Harman and his wife Lou, and annexed to Denver in 1896. As neighborhood folkore goes, Edwin was a decorated Confederate veteran and former lawyer and judge who became disillusioned with post-bellum life in Mississippi and decided to head West. I love that the original town hall still stands, always has the best flowers in summer, and has been tastefully renovated to host fancy community events. The city of Denver was founded in 1858, and Colorado did not become our 38th state until 1876, so this was all happening in a very short window of frontier history.

Beyond the local history, I also started to familiarize myself with the surrounding natural environment (Red Rocks, Front Range, Loveland Pass, Aspen, Durango, Mesa Verde and so much more… I took a week-long solo road trip through the Southwest), plants, animals (prairie dogs!), birds, bugs (cicadas!), weather (tornado warnings!). At first, I was still too burned out to do much socially, so I held off on engaging with the startup community or making an effort to find new friends beyond whatever happened naturally through day-to-day life. Through my responses to the warmth and outreach of others, I felt myself become nicer, less hard, less guarded. I started hosting small get togethers at our house. I was still pretty overwhelmed with my inner monologue, and didn’t really know how to explain myself if asked, “so who are you? what do you do?” but angel investment opportunities started to come my way, impressive local female founders.

Little did I know, time passing was working its subtle magic on me. Simply by existing, I was working through a lot of things during my experiment with retirement, which I branded as “professional sabbatical” since I didn’t know if it was going to be permanent. I felt myself becoming more stable and comfortable with my identity not being tied to my work.

How Am I Going to Pay for This?

I wrapped up the Mattermark transition in May 2018 and decided to use some of my savings to take the rest of the year off. To satisfy my need for an incremental spreadsheet to constantly iterate on, and because I finally had the time, I took over the “CFO of household” role from my husband for the first time in our 11 year marriage.

After an initial audit, which included calculating our net worth and IRR for the first time since 2012, I began thinking through how to diversify away from concentrated positions in startups and public stocks, and replenishing our retirement savings (Kevin had cashed out his 401k for a previous failed startup, so we were pretty behind where we should have been). I re-read “Your Money or Your Life” (thanks Dad for having that on the shelf when I was a teenager!) and began to engage with the FIRE movement (Financial Independence Retire Early) community to find more people like me.

When I say “people like me” I mean people for whom working or not is a choice, because they’ve accumulated the wealth required to deliver economic freedom. Living the lifestyle I want (which is not particularly frugal) entirely off the compounding returns of my investments, even at a fairly conservative growth rate on the principal, is an option for me now.

Can These Numbers Really Be Right?

Being young and in a position to never work again (at the 4% withdrawal rate, with some tweaks to my spending habits) sounds great and is literally the millennial dream if you spend much time on Instagram. I’m incredibly grateful that the stock I received for my work at Twilio ended up generating my wealth, but it’s also terrifying in the sense that it is all new and feels like it could disappear tomorrow.

After making my detailed spreadsheet it was undeniable: at a relatively conservative compounding growth rate, I could stop working and cover my expenses with my investment income and I would have more money than I’d ever need to spend in my life. It was very disorienting to have my net worth climb from something I hadn’t worked on since 2012, while my current efforts were amounting to nothing in economic terms.

I wondered if the math could really be right, and checked it a ton of times. I found it difficult to figure out who to discuss these questions with, since its taboo to talk about money in general, and retirement in your 30s specifically can trigger all sorts of reactions. Most of us have been fed the idea that retirement means we work until 65 and then take it easy playing golf, going on vacations, and buying a beach house, and never questioned that. As I reached out for advice I was surprised to find many people who are high earners but have very little savings. For them, talking to me about my plans brought up a lot of uncomfortable comparisons about life choices. I’ve included a list of resources at the bottom of this post for anyone who is curious to learn more about thinking through questions like this.

What Do I Do With All This Time?

Being on sabbatical gave me a taste of what retirement would look like for me right now: I had few friends or hobbies, no kids, and no long term goals or vision for my life. I had put pretty much all of this off while working on my startup, and then had moved away from my established community, habits and routines. I struggled to explain myself outside of my work, and even the creative things I had become good at didn’t ring true and I struggled to say, “I’m a writer” or “I’m an analyst” or “I’m an investor” or even “I’m an inventor” even though any of these answers is right. All this meant meaning-making was extremely difficult each day, and I started to wonder, “what do I do with all this time? is this all there is in life?”

For anyone who has ever suffered a bout of depression, these thoughts are warning signs. For me, I immediately began to build out lists of things I wanted to do, and fill my days with activities to stave off these thoughts. I spent a lot of time and money getting my hair done, working out, cooking, traveling extensively, and reading even more extensively. Each day I would write down everything I had done that day, and recite it to my husband. Thanks to a lot of time spent doing mindfulness training over the past few years, within a few months saw all this manic movement without purpose for what it was: a way to paper over my anxiety about my direction in life.

This is loosely written in chronological order, but for any reader who has made it this far I want to reassure you *I regressed many times* and it is still happening. It is not a linear path from not feeling okay about your life to feeling okay again, and I still have mornings where I wake up in a funk that takes me hours to shake off.

Why So Much Focus on Money?

Economic freedom is a powerful thing, and I growing up in the household of an entrepreneur I lived by the ebb and flow of the business and its income. When I started working as a stablehand at 13, for my Dad as an analyst at 15, at McDonald’s at 16, as a receptionist at the tennis club, as a tennis instructor for the Parks & Rec Department, as a barista, as a freelance website consultant… each move was a step toward freedom from the strings that came attached to my parent’s money, a step away from the financial precariousness that shaded my childhood.

Money isn’t something I hate, but I’m also wary of loving it. I don’t think it is a good idea to love tools you didn’t make yourself, or at least to love anything that is as fungible as money. What I love is freedom to live the way I want to live, do the things I want to do and also NOT do other things, and to be able to adapt to the world quickly and face the reality and consequences of my own choices. I’ve done several significant of “off script” things in my life including skipping the 4-year college checkbox, getting married really young, starting my own companies, and deciding to be childfree. There are many more that are too personal to share here.

Because of my tendency to do things that are at odds with what society tells us to do, I have assigned an additional level of responsibility to myself economically to always be able to protect myself from the potential fallout of being “weird” or different. Regardless of the fact that I enjoy a long marriage, I feel it is extremely important that I don’t need to rely on anyone else for money (or the protection it provides) and that I not subject my partner to a situation where he is carrying out the role of “Good Provider”.

So to simplify all this, I am focused on having money because it confers economic power, and economic power can be used to purchase freedom. Having the Freedom to live my life as I choose is my highest value.

But What About… You Know, Denver?

Denver’s great, but I can hardly claim to know it yet! It has been an excellent cocoon for me as I figure out what I’m doing with my life. The next chapter likely involves getting much more involved in the local community, doing a ton more outdoor stuff, finally learning to ski (lifelong snowboarder but I broke my ribs when I was early on at Referly without healthcare… long story) and so much more.

It took me at least 3 years to start feeling really at home in San Francisco, so I am expecting the pace for this will be about the same here. If you want to see the cool places I’m exploring, eating, hanging out etc. check out my Instagram – it’s public now so everyone can follow along as our puppies grow up!

Consciously Choosing Goals for Life in 2019

Given how much I love my freedom to live as I choose, you’ll probably not be surprised to hear that I am very into thinking through just what I should do with all this freedom I’ve earned. As 2018 came to a close I did my yearly exercise of writing down goals for the coming year. I chose 3 themes:

• Establish Creative Work Routine
  • I would like to be writing and painting (~4 hours per day), and I also want to explore startup ideas.
  • Grow BuriedReads.com
  • Launch paid associate-as-a-service newsletter
  • Start coding on personal CRM project
  • Continue XFactor partner role + angel investing
• Improve Physical Fitness & Appearance
  • I would like to have a slender, healthy, attractive body.
  • I would like to be comfortable on the floor with the dog, falling asleep, and doing athletic activities.
• Prioritize Making Memories
  • I would like to have a year filled with memorable experiences that honor my values, including outdoor exploration, live music, eating and drinking out and other fun stuff.

What you might notice is that nowhere in here did I say “I want to get a job”, “I want to get another dog” or “I want to buy a house”. Arguably, the three biggest decisions I’ve made in 2019 weren’t on my list. Thematically, I’d say the dog aligns with physical fitness and the job aligns with creative routine. But the house? The house is awesome, both emotionally and as an investment, and is totally the right choice. But it also reveals something about a hidden theme, perhaps the “why” behind these other themes.

The bigger theme is that I want to build a life. I am actually motivated to build my life up again, even though one lesson I’ve learned is the impermanence of it all. I found it a painful lesson to discover that sometimes good things (like startups you love or lifestyles in cities you love) do come to an end. I’ve realized that it doesn’t make the world a dark, bad, or hostile place and it doesn’t mean I’ve lost my freedom. Perhaps this is 1999 or 2006 in terms of market cycle, but this time I have so many more resources, and so much evidence that I can weather whatever storm comes.

Lead by Mary Oliver (listen to this poem read aloud)

Here is a story 
to break your heart. 
Are you willing? 
This winter 
the loons came to our harbor 
and died, one by one, 
of nothing we could see. 
A friend told me 
of one on the shore 
that lifted its head and opened 
the elegant beak and cried out 
in the long, sweet savoring of its life  
which, if you have heard it, 
you know is a sacred thing, 
and for which, if you have not heard it,  
you had better hurry to where 
they still sing. 
And, believe me, tell no one 
just where that is. 
The next morning 
this loon, speckled 
and iridescent and with a plan 
to fly home 
to some hidden lake, 
was dead on the shore. 
I tell you this 
to break your heart, 
by which I mean only 
that it break open and never close again  
to the rest of the world

---

Best Resources to learn more about FIRE (Financial Independence Retire Early):

There are a TON of resources for FIRE now that the movement is spreading, but these are the ones I found the most valuable.

Resources:

Playing with FIRE — Retirement Calendar

Books:

“Reboot: Leadership and the Art of Growing Up” by Jerry Colonna

“Your Money or Your Life” by Vicki Robin and Joe Dominguez (this is the original source of the movement, written in 1992!)

“Early Retirement Extreme: A Philosophical and Practical Guide to Financial Independence” by Jacob Lund Fisker

“The Millionaire Next Door: The Surprising Secrets of America’s Wealthy” by Thomas J. Stanley and William D. Danko

Blogs: Mr. Money Mustache (+ he has a coworking space here in Colorado!)

Podcasts:

ChooseFI

Naval Ravikant

Reddit: r/financialindependence and r/FATfire