Bootstrapped startups and the shit I learn in therapy

This year I used the Reflecting Forwards Notion template to do a REALLY in-depth personal year in review. Most of it I want to keep private, but I thought I would share a few excerpts here along with some pictures from throughout this crazy year.

I started a journal practice in 2020, here are a few highlights:

"If you're evaluating someone on whether you want to spend 60 years with them that's enough to give anyone cold feet. Instead ask yourself if you're enjoying spending time with them now, can you make plans 6 months out, can you enjoy a summer together?"

Esther Perel's theory of desire:

  • I want you more when you are in your own element because at that moment you don't need me. And if you don't need me I am not saddled with emotional responsibility towards you which gives me the freedom to want you.

March - Facing a possible recession. Feeling sick during the beginning of the pandemic, virtual birthday for Gianno. Anxiety over symptoms. Duck turns 14.

June - Getting real about what I want, mapping active projects, realizing I was stretched too thin, quitting Startup Grind. Burn out, kidney stone. Crash-landed the sailboat.

6/27 - Duck couldn't use his back legs, drop everything and focus on Duck

7/19 - I need to watch About Time at least once a year

8/24 - I was able to get a little of my excitement for work back last week

Operation mojo

  • Reign in working hours (stop at 5:30 max)
  • Have a productive morning
  • Stop shying away from hard/boring tasks
  • Get better at delegating
  • Work out 3 times per week
  • Make an effort to be social
  • Eat less sugar
  • Develop a non-TV hobby
  • Cut down on social media (30-day detox)
  • Guard morning time - calm mornings

Exercising is the linchpin, the habit that leads to better habits.

Long term goals

  • Partner I love
  • Audience growing organically
  • $60k in savings
  • $150k per year in income
  • 2+ sources of income
  • Do good and make my team rich
  • Mentally and physically healthy
  • Travel regularly


Core values: courage, empathy, love, creativity, honesty

If those are my values, my time was well aligned. This year has required a lot of courage and honesty. I've spent a lot of time at work figuring out how to lead, a lot of time in therapy addressing issues and working on myself, I spent time early in the year looking for a new partner, and then have spent a lot of time with Maddy once we were together.

There wasn't as much room for creativity as I would like. I had to spend a lot of time working on operations tasks this year at work, and I stopped writing publicly to give myself time to rest for the sake of my mental health.

I could have spent more time engaging in love and empathy, by doing community service or by visiting my friends and family (which was hard this year). Visits with my friends and family are highlights that stand out when I reflect on the year.

It also feels like there was too much stress. But that isn't represented in my values right now. Ideas for revisions to my values: health, happiness, beauty, balance.


I still struggle to stand my ground with clients and set healthy boundaries there. And with work in general, I struggle to detach and shut off.

I struggle to delegate and often let my weeks fill up with meetings that may not be totally necessary. I struggled to stand my ground with Curiefence about dates and pricing for their UX audit. And with Rebecca about minimums.

I struggle to turn off the TV, put down my phone, get off of Twitter. I struggle to maintain a healthy diet. Even now I'm likely going to order a cheeseburger on uber eats instead of eating the salad supplies in my fridge.

I struggled with maintaining healthy profit margins.


I'm proud that we donated almost $30,000 to social justice efforts, responded in an appropriate way, and increased the diversity of our team. I'm proud that we hired 4 people, plus Daisy. I'm proud that we launched 5 products for clients. I'm proud that we increased salaries and healthcare benefits during a pandemic.

I'm proud that I finished fixing up the sailboat and sold it. I feel much more financially secure now, and want to pay attention to that and maintain this level of personal financial margin. I'm proud of my apartment too, I love the way it looks.


I learn a lot in therapy. I learned (again) to be kinder to myself. I learned more about what I need to be happy (Operation Mojo). I learned how to differentiate problems and worries.

I learned a lot more about the issues in our country with social justice and racism. I learned more about my biases and how to build a diverse and inclusive team.

I learned how to speak up for my needs in a relationship without being passive-aggressive.

I learned that increasing the number of clients we work with is not the only path to growing our business. I learned about the importance of project and account managers.


  • How do we heal the divides in our country? Or should we?
  • Is violence ever necessary in creating systemic change?
  • What are my or my family's blind spots when it comes to our biases?
  • Are billionaires justifiable? Does it require exploitation to reach that level of wealth? If so, where is the line?
  • What is the right balance between growth and health?
  • What other black swan events will we experience in our lifetime?
  • How do I build enough confidence in my thinking to write about my opinions, while still being open to being wrong?
  • Do I have the energy to devote to another project?
  • How can I be consistently happy?

Moments of awe or wonder

  • Tipping the waiter at Taco Boy $100 for a $30 meal at the end of the year was one of the moments I felt best this entire year. I want to do more direct giving in the future.
  • Getting a tattoo with Abby was a really cool moment, and I loved hanging out with her and her friends around the camp fire.
  • Camping by the pond with Maddy and Duck, even though my anxiety was high felt amazing. I need to spend more time in nature.
  • Sitting on the deck of the spirit with Dan and fishing with him and Matt.

In the next year, don't worry so much. Be kind to yourself. Be kind to your dog. Don't let negative thoughts control you. Get outdoors, travel, be with friends. Don't push so hard, or spend too much time fantasizing about what you could have in the future. Learn to enjoy what you have in the present.

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