This is an article to my past self and perhaps those that come later who are in the same position I was in this time last year.
I love reflecting. It’s one of my favorite mental exercises to do. And especially in the month of December as the year is winding down and the peppermint creamer laces throughout my Saturday morning coffees. I think it’s important though to make this distinction. I don’t like to reflect so I can be critical or self deprecating. I like to reflect so that I can learn, apply, and adapt for things in the future. I don’t possess a rear view mirror from the standpoint that I don’t dwell on mistakes. I learn from them. My wife is still astounded that I’ve been fired twice, failed at relationships, had a couple of run ins with bad business partners, but yet I still move forward as if none of those things had ever happened. Shooters have to shoot.
Having a mindset built around adaptability through learned experiences has served me well and 2024 was no exception.
The Setting
I love a good origin story. How did this character get to this pivotal juncture in their life? What lead them to this moment in time where they chose to take the road less traveled?
I’ve been asked what lead me to starting my own business. What would posses me to do it with my spouse? And how in the world would I walk away from being a CTO, which is essentially the pinnacle of a career in tech. Or is it?
This time last year Elizabeth (my wife) and I were having discussions around what we were going to do in the upcoming year. I spent the fall of 2023 evaluating my options. I had developed this passion for creating developer content, but I was also feeling a strong draw towards being more present at home. A friend of mine gave me a very sobering stat that by 15 years old, you’ve already spent 90% of the time you’ll spend with your kid. That hit me like a ton of TypeScript code packing a punch greater than the node_modules required to run the script. I just didn’t feel like my priorities were aligned and that my skills were best being utilized.
I’d been building a software solution for 5 years as the Chief Architect and CTO. I had hired everyone in the technology department outside of 2 people. That was 35 + hires in 5 years with 25 of them happening in 2022. I had the team I wanted and was proud of the work they were doing, but I kept getting pulled further and further away from the Rust (see how I managed to slip Rust into a personal piece) and AWS I loved. I was coordinating, organizing, and delegating. All of the things I’d learned in my 15 + years leading people.
During this same fall, I started working with my friend Kirsty Norton as a career coach. We explored things like Core Values, Non-negotiable behaviors, finding my why, and what I wanted out of my career. In real life, I’m not a sensitive person. I’ve cried a few times in my life. I don’t like physical touch. I don’t not process my feelings, but I do so in a very logical and methodical way. Call it nature and nurture in my case as I know how I got here. And none of this is to say you should be like me or do it my way or to imitate some form of male toughness. It’s all part of the origin story. The who I am is what made the exploration with Kirsty so life changing. It’s the holidays, so perhaps my heart grew three sizes that fall.
And lastly, I was doing what I’ve been recommending so many do on social media, leverage your mentors and friends. I had 7 people in my career not part of my family that I was bouncing this idea of “doing my own thing” off of. And all of it culminated at re:Invent of 2023. That week in Las Vegas was transformative for me which then shaped my willingness to think about our life (our life == Elizabeth, my kids, and I) differently. You see, my wife is my best friend. Always has been. And any decisions that impact our world are always locked in together.
It all came down to this time last December.
Note to Myself
Looking back on where I was last winter and where I am now, what would I tell myself. What are the things that have rang true that mattered. And what are the things I struggled with that will be OK. And what have I learned and advice for the future.
What Ended up Being True
Family
The desire to spend more time with my family proved to be worth the leap. This year, we traveled to New York City for Datadog’s DASH, took multiple trips to see my mother in Lafayette, and did a week at Disney World in September. Having the flexibility to work my schedule but also more normalize and smooth my supply was huge. By being deliverable focused and not schedule focused, it has afforded me the space to use the time in blocks that fit the setting. For instance, I might have been in Orlando, but I could still step out of a line to take a phone call. Or I could produce a report or reply after hours. In a normal work setting, you have standup, scheduled meetings, and my day was more rhythmic than dynamic.
The second part of this was that by partnering with my wife who is a 50/50 with me on the company, it made it less scary. Sure, I’m billing more hours and projects than she is, but she’s invested. She’s the balance that I need. She’s helped on contracts, pricing, marketing, SWAG, and scheduling. She’s not an admin, she’s the COO and CFO all rolled into one for our business. We’ve also been able to incorporate our children. Dinner time business discussions, cash flow, and saving for a rainy day are all things that will make them better as they get older. When your kids are home schooled, everything can be a lesson.
Take the Leap
I was ready to take the leap. My mentors and peers encouraged me to make the move. I’ve developed a very particular set of skills which I acquired over a long period of time.
I’ve been very clear over the years, my skill set paired with my personality isn’t common. Being able to talk to a CTO about roadmap, cost and budget, and product market fit while also having an in-depth discussion with an engineer about how to solve a complex problem in their domain isn’t something they teach in school. It also wasn’t something that I set out to do. Join all of that with a desire and heart for people, and it’s something that can always be in demand.
I didn’t quite believe that last year. I took a leap though and looking back. They were right.
What will be OK
Sales and Pipeline
I’m constantly stressing on some level about sales. The act of building a pipeline is still tough for me. Everything I’ve done this year has been through word of mouth or through a relationship. I hope that holds true in 2025 because it’s an easier start into an organization by being a known quantity. I’m not one that struggles with building relationships but leveraging them for business purposes has taken some time but I’m starting to realize that it’s how a lot of this works. And by leaning in vs being shy, things will be OK.
Insurance, Taxes, and the Back Office
These are the things that you don’t really think about until you have to. But again, I lean on my wife for so much of this. Running a business isn’t always about taking care of customers, but what I try to do is automate and invest in tools and people that are at the right price freeing up time to spend more time on the work I need to do.
As for insurance, you can, and we did, find quality insurance at a reasonable price. Having a family and especially an active family forces you have the right coverage. I had some concern about this upfront, but once we found some qualified professionals to help, it’s been mostly a non-issue.
Taxes are another one of those items that I have to take care of. Taxes have to be paid both the right amount and on the right schedule. I have a bit of a cheat code again with Elizabeth as she’s a CPA with a license in our incorporated state. Pair that with QuickBooks and things have been OK in this area.
What I’ve Learned
I’m a White Collar Uber Driver
I had these notions of taking my cloud architecture in AWS skills to the masses and everything would be gravy from there. I don’t know that I was naive but I think I was pigeon holing myself into one part of my experiences as the backbone for our business. What has ended up happening is that I’m using all of my skills across a variety of customers and it’s way more rewarding. Had I just being doing cloud architecture day after day after day, I don’t know that I’d be as satisfied.
I’ve taken this approach that I’m driving an Uber and picking up new customers and helping them get to where they want to go. Of course, sussing out the destination is part of the gig. But for some that is cloud architecture. For some that is a Kubernetes implementation. And for others, it is needing a fractional CTO as a bridge. The truth is, and I’ve said this before, I like solving problems. I like to believe Sherlock Holmes loved the variety in his job too, and that’s often how I see myself. Investigating, strategizing, and implementing something that makes people better.
Save, Save, Save
There’s a large gap for most of us in terms of what we need and what we want. Life has gotten increasingly more expensive, but with a business that is dependent upon customers for revenue, it’s been critical for us to put 6 months of income away “just in case”. I don’t know that I believe that this is any different than when I was working a regular job, but it’s funny. When I’m responsible for the income coming in, I’m a little more of a steward with it. I liken it to hunting or growing your own food. For some reason, you take better care of it. Perhaps there’s an ownership or accountability piece in there worth exploring at some point.
But the lesson here is that it’s important to plan for the unexpected. I watched my father do it for years running his own business and I have a great appreciation for his diligence at this stage of the game. And I’m sure this’ll deepen.
Takeaways
If I was reading this and thinking about doing something similar here are 3 tips I’d give you about getting started.
- Figure out why you want to step out. What specifically are you looking to achieve. If it’s to not work for anyone, you’ll be disappointed because while I am the boss, I actually have more bosses now in my clients. Sure, I can quit them at any point, but that’s bad for business and bad for revenue. So you can’t quit your job so you don’t have to work with people anymore. But find your reason. It’ll be your anchor.
- Lean on your mentors and peers. If you don’t have, finding them is step one. But step two is to leverage your relationships to help you spot holes, think about the future, and validate the course you are thinking of charting. I can’t stress this enough. Find some people to hold that mirror up to you. Look in it. See if what you think you see is what you want. And if it’s viable.
- Don’t be afraid to fail. I wrote about Quitting Tomorrow recently and if you followed that piece, it talks about training Jiu-Jitsu. The thing about the sport is that you lose ALOT. I mean ALOT. Especially as a beginner. But one thing you don’t talk about is losing. You talk about learning. And such is the same when starting your own business. You will win some and learn a whole lot more. Be open to the learning. Embrace the suck and refine. You’ll constantly be learning early on, so get used to it and make the most of it. Because you are the captain of that ship.
Wrapping Up
It’s days before Christmas and my second cup of peppermint infused coffee is almost gone. I hope this article gave you a little more insight into who I am and how I got here. It’s been a cathartic release of reflection on my end.
My wife and I were talking the other day. This is 100% not where we thought our life would be when we got married all those years ago. But neither of us would change it and we are excited about the future.
If I can leave you with one last parting piece of advice.
Find joy and meaning in your day to day. Tomorrow is either going to come quickly or it’s not going to come for you at all. Don’t waste your being on things that don’t matter.
Thanks so much for reading!