Bootstrapped startups and the shit I learn in therapy

I love annual reviews. Weird, but true. 

I love reading other people’s year-in-review posts and taking the time to do my reflection each year. 

For the last couple of years, I’ve been tweaking the format of my own review process. In 2020 and 2021 I used the Reflecting Forwards Notion template and then pared it down for my public posts. 

It’s an interesting template, but it’s super involved and started to feel too burdensome. I was dragging my feet so much that I didn’t actually do my review for 2022 until AUGUST of 2023, and by then I just said to hell with the template and asked 3 questions:

  • What went well?
  • What didn’t go well?
  • What did I learn?

This year I’m trying to find a middle ground. I created my own template that pulls a couple of things from the reflecting forwards template but simplifies it and restructures it a lot. I kept the research portion, where you pull from journal entries and photos throughout the year. And I kept one of my favorite sections, moments of awe or wonder. In total I have 9 sections:

  • Remember - journal entries, photos, etc.
  • Career
  • Finances
  • Fitness
  • Hobbies & travel
  • Relationships
  • Mental health
  • Moments of awe or wonder
  • Goals

You can find my Notion template for free here. Feel free to duplicate it and tweak it to find what works for you.

For this post, I will keep a simplified format similar to last year. Both to keep the post from getting too long and to moderate what I share publicly. I’ll have 5 sections:

  • What went well?
  • What didn’t go well?
  • What did I learn?
  • Moments of awe or wonder
  • Goals

So let’s get into it. 

What went well?

My finances are in a better place than they ever have been thanks to the sale of Krit and my savings from my GreyNoise salary. I am back to worrying about money a bit, for some valid reasons I’ll get into a bit later. But I’m doing my best to keep that in check. 

Posing at the 501km mark with my Camino family
Posing at the 501km mark with my Camino family

My biggest win from this year was taking a lot of time off and hiking the Camino de Santiago. This was a dream I’ve had since the 8th grade, and the experience blew me away. I met so many amazing people, and I got to share part of the experience with my partner and sister. And taking a lot of time off really helped me recharge and get ready to tackle some big projects in the new year. 

In preparation for the Camino, I started taking Spanish lessons and got back into backpacking. Both of these brought me a ton of joy and fulfillment this year. 

I took Spanish classes online through a school in Mexico (cannot recommend them enough). I loved the process of learning something unrelated to work, and found myself enjoying doing my homework (although I still put it off to the last second every week). 

Exploring Grand Isle in Lake Superior, Northern Michigan
Exploring Grand Isle in Lake Superior, Northern Michigan

It felt so good to get back into backpacking. I did 3 trips in Michigan, plus a multi-day camping trip with some day hikes. Backpacking has always been an incredible mental reset for me, and I had forgotten how much I need that.

Swimming with Maddy in a cenote in Cancun, Mexico
Swimming with Maddy in a cenote in Cancun, Mexico

I also surprised my partner with a trip to Mexico for her birthday, which was a goal of mine going into the year. That trip was absolutely incredible. We swam in cenotes, relaxed by the pool, and had no stress for several days.

I traveled a ton this year (Mexico, Northern Michigan, Spain, Italy, Niagara) and really enjoyed life outside of work. That's a big win.

The annual Star Wars party in Detroit with my friends.
The annual Star Wars party in Detroit with my friends.

What didn’t go well?

The biggest challenge of this year was getting fired in July. I haven’t talked about this much publicly yet, because I’m still working through it. But I do hope to write about it more someday, having now been on both sides of the process (firing someone and getting fired). 

Overall it was painful, but for the best. I’m very grateful for the time I had as an employee after selling Krit, it was a great learning experience and I met some wonderful, kind, brilliant people. Unfortunately, I wasn’t the right fit for the role I was in and it wasn’t exactly the right fit for me. So in the end, I do think it was best for me to leave.

The experience led me to take a longer sabbatical than I had originally planned, with no work projects or expectations hanging over my head. I was able to walk the Camino totally free of obligations. And it gave me the push to go out on my own again (more on that later).

While I think on the whole my mental health was better this year than it has been in past years, there were moments where I didn’t handle stresses I was dealing with as well as I would have liked. I got away from some of my good therapeutic practices (journaling, meditation) which would have helped with those moments, and my anxiety has crept back up again. So next year I’m going to be focusing on building good habits to help me manage my stress and anxiety. 

The Cruz de Ferro on the Camino de Santiago. Tradition is to bring a stone from home and then leave it behind at the base of the cross along with all of your burdens.
The Cruz de Ferro on the Camino de Santiago. Tradition is to bring a stone from home and then leave it behind at the base of the cross along with all of your burdens.

What did I learn?

  • I learned a lot about how networks and the internet work at a low level in my time at GreyNoise. 
  • I learned that I can survive a big professional failure, and that as long as I live by my values and treat people with respect that will ultimately be more important to the people around me than the failure was. 
  • I learned that not only CAN I walk across a country, I LOVE the simplicity and the community and the challenge that come with a big through hike. 
  • I learned that I shouldn’t be afraid of crowds on big through hikes, because the people are the best part. Walking the Appalachian Trail is my newest big audacious goal (although not for this year).
  • I learned that, at least for now, I want to be a founder and not an employee.

Moments of awe or wonder

  • Swimming in the cenotes in Mexico with my partner Maddy. By chance we were the only ones who booked our tour, and so ended up with a private guide and photographer.
  • Finding a sinkhole lake on my backpacking trip with Maddy and having it entirely to ourselves.
  • Seeing Maddy and our friend Leanna experience Pictured Rocks for the first time.
  • Experiencing Niagara falls for the first time with my climbing crew. 
  • Spending time with my family at Drummond Island in Northern Michigan.
  • Feeling all of the love and support from my coworkers when I got fired.
  • A bunch of my closest friends got married this year, and all of the weddings had some incredible moments. I love weddings, and this was a year of very good weddings.
  • So many from the Camino. Meeting Maria while waiting for the train to Pamplona to start my Camino, and running into her again just before the end of my Camino. Drinking wine with pilgrims on the bridge on my second night after a fabulous community dinner. Singing 2000s pop at the top of our lungs with my Camino family while walking across the Meseta. Crossing the finish line with my sister.
The house I stayed in my very first night on the Camino. Another moment of awe.


2023 Goals

  • Theme: Living and learning
  • Hike the Camino de Santiago ✅
  • Take Maddy on a surprise trip ✅
  • Have a 5-minute conversation with a friend in Spanish ✅
  • Climb 2x a week for two months ❌
  • Build emotional resilience ❌

I did pretty well with my 2023 goals. Hiking the Camino, surprising Maddy, and sticking to Spanish lessons for most of the year were big achievements. I didn’t climb as much as I had intended, but I did pick up weightlifting for a bit and really enjoyed that again. And I don’t think I built emotional resilience, or at least not at the level I would like to have gotten to. But I did weather some big life changes and challenges, so that is really the only way to practice. 

2024 Goals

  • Get a new business to ramen profitable
  • Take couples counseling
  • Go to Mexico for a week
  • Go on a weeklong backpacking trip
  • 10 pushups, 10 situps a day
  • 10 minutes of meditation a day
  • 10 minutes of writing a day

In 2024 my big focuses are going to be my relationship, getting my mental health in a really solid place, and growing a new business. I think every couple should do couples counseling, it’s a great way to strengthen your relationship and build strong communication skills so I’m excited to try that this year. The last three goals are all about building the daily habits to get my mental health in a really solid place. 

And then if I can go on at least one weeklong backpacking trip and take a weeklong trip to Mexico I’ll feel like I’m continuing the spirit of adventure from the Camino into this year which would be a big win.

Overall thoughts

Overall, this was a weird year. It didn’t go down how I expected. But it was a fantastic year, in spite of the challenges. I feel so lucky to have had the experiences I had and to be where I am now. 

Thanks for reading! If you'd like to read my past year-in-review posts you can find those here. Hope you have a great year.

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