Bootstrapped startups and the shit I learn in therapy

The tips of my fingers started to tingle, like tiny pins were being slipped beneath my skin.

My chest got tight and I felt lightheaded, almost dizzy.

It wasn’t carbon monoxide poisoning, the fancy alarm I bought the night before told me that levels were normal. I wasn’t having a heart attack, I had gotten an EKG a few months before when the chest pains were more intense. The doctor looked at me when I told her I wanted to get my heart checked and almost laughed, “how old are you?” I was 25 at the time.

I hadn’t completely ruled out brain cancer yet, I wasn't scared enough to fork over the cash for a CAT scan. I didn’t need it, I knew the problem was in my head. But it wasn’t cancer, it was anxiety.

I don’t know exactly how many panic attacks I’ve had between 2018 and 2019, more than one and less than 10 would be my guess. It depends when it crosses the threshold from anxiety to an attack.

Anxiety exercise
When I was feeling an anxiety attack coming on I would draw squares in my journal, breathing for 4 seconds on each side.

This year was incredible in so many ways.

I restored my grandfather's 22 ft sailboat.

I was in the final month, and the woman who owned the trailer I was keeping it on was getting restless. I had originally told her two months, but hurricane season had come and gone and I was still working.

Finally, I was ready to sand and paint the bottom, the final task before I could get it into the water. My dad came down for the weekend to help me and without the proper tools, it was grueling work. We rigged up a jack and spent two days coated in sweat and toxic paint. On the final day, we were almost done, working underneath the boat when it started creaking. The boat fell forward, coming off the jacks almost entirely.

We were both fine, completely unharmed. But the trailer took a chunk out of the keel. Just as everything was almost ready to go, it would be another week at least before I could even start this newest repair.

I kept waiting for my uncle to help, but he was sick and I was past out of time. He pulled himself out of bed, came to look at it with me, and then I got to work. I got it back on the jack myself and applied my first fiberglass patch.

My first fiberglass patch

Repairing the boat required help from family and friends, a lot of time and a lot of sweat. I wrecked my budget, got eaten alive by bugs on multiple occasions, and felt in over my head from day one. But it was the first time I'd ever done anything so hands-on. It built a whole new kind of confidence.

I jumped out of a plane with my sister for her 21st birthday.

One of the great joys of my life these days is my relationship with my younger sister. The older we have gotten, the closer we have become. So I knew I wanted to do something big for her 21st birthday.

I suggested we get a tattoo together, something we'd talked about for a couple of years. But she had another idea. What if we went skydiving?

I booked the tickets, and when the weekend came drove up to Columbia. I surprised her at a tailgate party with a cake and her friends helped me thoroughly embarrass her by singing Happy Birthday.

The next day we made the trek together to the jump zone. It's amazing how little information they give you before you're suiting up. On the way up the photographer asked her how she was feeling. "I really don't want to talk right now."

I expected to be excited and scared. What I didn't expect was how much self-confidence you feel when your feet hit the ground. Your whole life you're told that falling out of a plane, or even just the door opening, is the worst-case scenario. Willingly jumping out is one of the most empowering things I've ever done. Doing it with my little sister, and seeing the excitement on her face when we landed, made it so much better.

I grew Krit to over $700,000 in revenue

This year we very nearly doubled our revenue for Krit, the software agency I started and run. We grew as a remote team, fired 2 problem clients, started working with one of my best friends, moved into a new office, held our first retreat, and issued bonuses to share the profits.

We've invested serious time into our processes so that we're on more solid ground than we've ever been on and are set up to grow again in 2020. I spent a lot of time towards the end of this year thinking about what that growth will look like, and I'm excited for what the future holds for our talented team.

But more than anything else I'll remember 2019 for my growth as a person.

I will remember the fear, anxiety, and loneliness that wracked me for much of the year. For the first few months of 2019, I was afraid of the weekends because I was afraid to face the anxiety alone, afraid of another panic attack.

Over time that fear morphed from the intense physical feelings to a subtler, more dangerous type of anxiety. Fears that I was suffering from a horrible illness, or that I might hurt myself or someone else. Even when I looked okay on the surface, for much of this year I've dealt with dark automatic thoughts.

It started to change when I owned up to some really fucked up things I did when I was younger. It changed when I learned about the danger of shame, when I recognized that all of these fears were related to a feeling that something might be irrevocably broken inside of me, when I saw that those thoughts were their own form of narcissism, and when I finally started to be kinder to myself.

All of this happened with the help of lots of therapy, my incredible family and friends, and a lot of work to develop healthy habits. Habits that give me the space to process, think and move forward.

I'm still not done, I won't ever be. I've made a lot of progress though.

So when I look back on 2019 I'll remember jumping out of a plane, restoring a boat, and working to grow the company. But the thing that will stand out the most is working through the inner struggles and finding some peace.

Be kind to yourself.


2019 goals

  • Create more than I ever have before ✅
  • Learn to be happy being single ✅
  • Find out more about what I want in a life partner ✅
  • Take a big solo trip 🤷‍
  • Increase my personal earnings ✅
  • Spend more time outdoors ✅
  • Workout more consistently than I have in the past ✅
  • Help others ❌

Random stats

  • 4 weddings attended
  • 2 friends had their first baby
  • 8 first dates
  • 1 new relationship
  • 3 new states
  • Way too much money spent on food & alcohol
  • 18 blog posts
  • $2,457.70 earned from side projects
  • Lots of exercise, meditation & therapy

My takeaway is that setting intentionally vague goals was really helpful, at least this year. I care more about the process and the intention than an arbitrary number. That said, I am going to try to make my goals a little more specific (but hopefully still achievable) this year to compare.

2020 goals

  • Meditate every day
  • Exercise 3 days per week
  • Write 1 sentence for my personal blog every weekday
  • Eat less fast food
  • Volunteer once per month
  • Hike or travel once per month
  • Sail twice per month
  • Set a consistent morning routine
  • Continue spending lots of time with friends & family
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