My 4 Part Transition Plan from Full Time CTO to Indie Hacker

For more than a decade now I've been working as a professional web developer. My journey took me from a young man freelancing and offering any digital skills he could muster, to working as the CTO of a quickly growing web agency for the past 5 years. During this period I made my living off of servicing others. It paid the bills well and grew my professional career enormously.

However, when I look back, I realized that my biggest leaps in actual talent all came from the independent projects I took on that were ever so slightly out of my current capabilities. When I was a graphic designer as a kid my dad encouraged me to learn how to upload a static design to a web server so I could maintain his website. I made the leap from photoshop which paid the bills to slicing up the PSD and publishing it with Dreamweaver. This didn't make me any money, but it was one of those first leaps that made grew my skills and subsequently opened more doors to monetize these new found talents. I began taking requests for websites.

A similar leap came when I was primarily a frontend web developer, given my graphic design background. I had made a good living up until this point as a front end specialist. But I wanted to merge this passion with another in gardenening. So I started another project, just out of reach of my skills (oakparks.org – a plant database). This introduced me to full stack development through the use of the Laravel framework. It allowed me to realize I actually really enjoy working at the data level. It somehow seemed more powerful and more importantly, less subjective.

My point is, everytime I became a professional at something it paid the bills and I could've made a living from it if I had stayed the course. But it was always independent projects that I purposefully chose to be an arm's length outside of my wheel house that always exceptionally grew my talents. The projects I built usually weren't monetizable right away, but the new skills derived from them inevitably multiplied my value later on.

This brings me to what I think is my current leap. My bills have been paid for the last 5 years as the CTO of a web agency. But my skills have stagnated along the way. The ones I already had have become very refined, don't get me wrong. But there were also many that have been sitting just far enough that they never warranted me playing with them because they didn't directly make money for the agency. Given my past success, I decided to jump.

I was a decent CTO, but I knew I had potentially much greater skillset in my ability to quickly and efficiently launch small product start ups. I just had to master a few more hard and soft skills.

Hard Skills

Typescript
Go Lang
Edge Computing
Machine Learning
Large Data Handling

Soft Skills

Writing
Developing a voice and online persona
Video Production
Community Engagement
Latest Digital Marketing strategies

New Year New Me

I left my job as CTO at the end of 2022 and so I began formulating a plan around 2023. I found over the past few years that working in yearly quarters gave a good natural cadence to business development and so I kept with that. I divided my year into four.

Avoiding the Trap

I wanted to stay humble in my approach and so I knew there was a trap I wanted to avoid: wasting time on the elusive big fish. I think the absolute worse thing I could do in a situation where I needed to replace my old salary with some sort of recurring product revenu was build something for an entire year thinking my brilliant idea can't fail only to find out that statistically brilliance is a rare thing in the starry sky.

OK, so I should break things down into small enough chunks that can be finished in a reasonable amount of time. This made sense. The smaller scope of my projects meant they didn't have as high of a monetary return, but it did mean I could avoid wasting time but seeing their direction as early as possible.

There was another problem though. I usually have tons of ideas when I'm working in my field, but over the past couple of months between leaving my job and planning for the next big leap, I seem to be coming up a bit short. The inspiration was drying up. This led me to another important realization. Theoreticizing about potential solutions to problems you're not even working on is a recipe for disaster. It's disconnected from reality and has a high chance of failure. My best ideas came in the areas I was working on. Ideas that solved real problems I was having myself in areas that I knew intimately.

Ah ha. But I was no longer toilling away in these areas. So I lacked the necessary inspiration. I guess I should start working on stuff regardless of their potential. In fact I should work on as many different things as I could to maximize my exposure to different verticals. Coupled with my affinity for calendar quarters I came up with the following phases for my new year of indie hacking.

Q1. High Volume for Inspiration

This phase is comprised of more or less one rule. Build something every week. The whole purpose of this phase is to build momentum in creating things, while staying focused on launching as quickly as possible. The frequency of projects at the weekly level keeps me focused on what's most important while allowing me to dive deep, although briefly, on a variety of potential verticals and technologies.

Making money is not the point here. I'm laying a foundation of generating inspiration and also seeing what projects are more "sticky" than others. Building in public is a big part of this too since I want to leverage everything I'm doing to generate online interest while honing my soft skills in these areas. These projects are mostly free things since it's highly unlikely I can build something worth charging for in a week. Nevertheless, they may be valuable in their rudimentary form to some people. Knowing which ones get some natural traction could inform me which ones to bring over to the next phase or iterate over.

Q2. Medium Volume for Learning to Monetize

In this phase, I plan on building 3 products, 1 each month. Obviously this allows me to output a better quality and so I plan on charging. How much? Anything, 1$ maybe. It doesn't really matter, the point is to prove I have some sort of product someone somewhere is willing to pay something for. Hopefully the knowledge gained from Q1 will give me an advantage in choosing what products to focus my build towards.

Q3. Focus on the Winner and Build Something Useful to Completion

At this point, I hope I will have a product MVP that has proven it can be monetized. But what's its ceiling? This phase is meant for developing something from an MVP to a proper product that I would feel proud to charge users for. This still isn't a big fish. My goal here is to build up to something like 500$/mo. This phase focuses on only 1 product, whether it's something carried over from previous phases or entirely new but hopefully well informed and inspired. I'll probably have an early development phase where I focus on refining it and adding the most valuable features and towards the end of the quarter focus on the marketing angle to build towards the monetary goal.

Q4. Reassess, Double Down on What's Working, Toss What's Not

Obviously $500/mo isn't a livable salary. Far from it, at least for my spoiled western butt. But the whole point was I built something that has proven potential and didn't waste a year of my time. And so at this point I'll be looking for everything done right and wrong so I can either double down what's working and maybe bring the current revenue to a new level, or prepare to repeat the process with another small humble project again. There's much less risk in building 5 products that bring in $1000/mo then spending an entire year trying to build a $5000/mo SAAS that can easily flop.

Among those 5 products is more opportunity to nurture the aspects that the market encourages and get rid of the stuff that's a dead end or has a tiny market cap.

This is my plan. To be honest, it's probably over planned and rigid and would benefit from some adaptibility as I go. But I work well with strict structure and so is my 4 Part IndieHacker Transition plan. Please follow to see if it has any merit.