Going Indie: A Life Design Choice

How a career meaning crisis lead me to one of the biggest shifts in my career: going independent

The Meaning Crisis

“Sounds more like a meaning crisis”

These words came from an unlikely person. From the depths of prolonged burnout from my job as a software developer, I reached out to as many connections as I could to see what my alternative options were. I ended up in the office of an accomplished CEO, “Someone I just need to talk to” according to the friend who set up the meeting.

I sat there, sipping coffee, pouring out every last thing that bothered me about my current predicament. If it was supposed to be some kind of interview, I threw that out the window and steered straight into a full blown therapy session with this person I just met.

“I’m just burned out” I said to conclude my extended tirade but after careful listening, their response was a gentle but firm correction. It wasn’t burn out, it was a damn meaning crisis. I wasn’t overworked, if anything I was underworked. I just lost the grip on any meaning I previously held in that role.

The feelings of burn out and those of a meaning crisis are imperceptibly similar but the actions required to address each are quite different.

The Senior Talent Dilemma

A common gripe amongst senior developers in the industry is that at some point the only way to progress your career is to become a manager. And then a director. And then a VP of engineering and so on.

I knew very early in my career that management was not for me. After only a few years as a developer, I stepped into my first management role and immediately regretted it. The meetings and bureaucracy were as advertised - dull and dysfunctional. Is this really how decisions are made? A bunch of people sitting around a conference room trying to look smarter than one another? They’re not even working together - they’re working against each other. Am I the only one that sees this?

I felt alone and missed doing the things that got me into software in the first place. Programming, problem solving, building things. I was good at those things but surely had so much more room to grow in my craft. Why did I stop? Now I was stuck - on a track that seemed impossible to step off of.

“It’s a good career step” is what people told me - what echoed in my mind as I sat there wondering why I should stay on the management track. Was it though? A good step towards what? Towards more management? Towards managing more people? Do I really want to manage the managers?

How often do people do that? Tolerate unsavory work because it’s “a good career step”. Long hours, the grind, whatever it is to get to that next level. When does it end? What is the destination?

The one thing I unquestionably wanted was to progress. To feel like I was growing and achieving something, each and every day. But what does it look like to progress if not up the corporate ladder?

This is the senior talent dilemma: When your skills as an individual contributor are proficient but it isn’t clear how to progress without leaving those skills behind and stepping into management.

Designing Engineering Career Journeys

Through careers dilemmas and crises of various sorts, I chose to take action instead of wallowing in my own complaints about “the industry” and its broken employment models.

A few years into my role at one company, it was evident that the senior engineers around me had the need to progress. It was a smaller company but had a few dozen engineers and most of them had the title “Senior Engineer”. In fact, there was only one other possible title in engineering, just “Engineer”. The senior engineers, myself included, wondered how one might progress in this environment. How do I get a raise? How do I get access to different types of opportunities? How can I advance my career?

My prior frustrations pushed me to solve this one, for myself and for those around me. I had experience in larger organizations that at least had something and we felt like we had nothing so surely it wouldn’t be too hard to make some improvements?

This was the most energy I’ve put into organizational change management in my life. I spent months working with engineering leadership, HR, etc. to define new roles and career paths. We started from scratch, researching what other companies did. I interviewed every single engineer in the organization, trying to find what they really wanted and what would work for them.

Naturally, one of my primary goals when designing career paths was to support both management and individual contributor tracks. We introduced roles like Staff Engineer, Principal Engineer, etc.

We also introduced functions like “Architect”, which was one I pushed hard for because I felt like certain people (ahem, me) were already playing this role and everyone deserved clarity on what the role means and what an architect is responsible for.

While this organizational redesign was a large improvement over the nothingness that came before it and many engineers benefited from it, it wasn’t able to stop my unwitting march towards a meaning crisis.

The Architect Debacle

You would think that after spending months designing roles for an entire organization and specifically documenting expectations for my own role would yield an optimal result. Very few people have such an opportunity so this was a golden one for sure, right?

Wrong.

As it happens, the perception of what an architect does and does not do is comically disparate depending on who you ask. Not too long after I donned the architect role, a chief architect was hired and an architecture committee was formed. I had nothing to do with this hire and certainly did not form this committee though I was invited to it because I was the only one around who carried the word “architect” in their Slack profile.

“What does a chief architect do?”, “What is the architecture committee responsible for?” were the questions that came to mind. I never did get straight answers up front but over time I learned the answer to both is “Not much”. Meetings, diagrams, lots of questions and very few solutions to anything. I was the only one in the committee that was actually writing code regularly and that continued to diminish as time went on. The only way I could do actual coding was on my own time and on my own self-direction. The engineers who came to me with real architecture questions and needs were often disappointed when I told them I could no longer fulfill the documented responsibilities of an architect - the ones I helped write.

Instead I stepped into meeting after meeting, mostly playing defense on various hair-brained initiatives that would have been immediately rejected by any reasonable engineer or product owner if it came to their queue.

The role I spent so long fighting for slipped away in less time than it took to incept it. I wasn’t happier, I wasn’t contributing more, I felt like I was contributing nothing.

Half in jest, I removed the word “architect” from as many places as I could and replaced them with “Mediocre Developer” to annunciate my newly formed disdain for titles as they were clearly meaningless no matter how hard we tried to define them.

Designing Your Life

Life problems are design problems and can be solved for just like any other design problem. This is the premise of the book “Designing Your Life” by Bill Burnett. Now deep in what I believed to be burn out, I attended a multi-week Designing Your Life workshop to see if it could achieve anything useful.

One of the ongoing exercises in this workshop is to keep a Good Time Journal, documenting your daily activities and identifying engagement and energy levels in each one. Unsurprisingly I was writing “Low” for almost every activity occurring at work. Meetings, committees, dealing with people problems, etc. - it all sapped my energy.

My “High” points were usually at home, doing things with my kids but I did have a few insightful moments at work that did energize me: working with peers either individually or in small group settings and also some technical side projects that I was able to indulge in when time permitted.

The volume of “Low” points merely confirmed what I already knew - something needed to change and quickly.

The final exercise in this workshop is called Odyssey Planning where you identify a few possible paths and document things like timeline, resources required, confidence and coherence. Mostly you’re just trying to identify how much a possible path aligns with your life needs and whether or not it is feasible.

My three possible paths were identified as:

• Starting my own company

• Continuing as an “architect” with some modifications

• Quitting and joining a new company

Prototyping as a Founder

Like any design problem, prototyping is an important part of life design.

You wouldn’t build and launch a product without first building a smaller prototype first, right? So why would you make a major life change without first trying it with as little risk as possible? This was my mistake in my first foray into management all those years back. I just jumped right onto the track with both feet and it was very difficult to move away from that.

Of all of the options in front of me, starting my own thing was the one that spoke to me the most. It’s something I’ve considered for such a long time and felt like the destination I was walking towards. I knew the traditional corporate ladders weren’t for me but starting my own business was a worthy pursuit and one that I could continually progress towards.

I’ve been around enough founders and read enough testimonials to know that this was no small decision. Starting a business comes with risk and takes a huge amount of commitment and resolve to be successful. While I am confident in my abilities and my resolve when my mind is committed to something, I wasn’t exactly convinced that starting a company would solve my life design problems. Would I simply be trading my current meetings with investor meetings or sales meetings? How much time would I actually get to spend building things? Would I be truly free or would I merely be a slave to the startup grind for the next decade? What if I don’t like the product I built or the space I build it in? What if I’m uncomfortable with the uncertainty of a steady pay check?

For my prototype, I decided to build and sell my own course for developers. This is a common activity for people considering a solopreneur route, so this was my opportunity to try that out. I already had my own technical blog with a few successful posts and could advertise the course there. I didn’t want to quit my job just yet since it would take a while to build the course and I really had no idea how well it would do or if I would even like it.

I woke up at 5am almost every day for about 6 months researching, coding, recording and editing for the course. It was hard work but I loved it. I loved the feeling of waking up excited to work on something again. I loved empathizing with developers and what they would value, strategizing my marketing plan and seeing my blog traffic increase as I published content related to the course. I loved doing things besides coding - this is when I learned that I have some skill as a writer and that I actually enjoy some aspects of marketing.

While building a solo course is not quite the same as being a startup founder, I got a taste of what it feels like to be a founder and really came to appreciate the founder’s mindset.

Pick Your Problems

A very useful way to evaluate your choices is to pick your problems.

It is too common for people to focus on the benefits or the upside for their choices, but ignoring the problems is a mistake. Every difficult choice comes with a set of problems and it’s important to acknowledge those and expect them. Whenever you make a choice, especially a major life choice, you are indeed picking your problems.

In my solopreneur prototype, I learned that I would be choosing these problems:

• Loneliness

• Limited upside

• 100% self-dependence

• Long-term commitment to one thing

• Spending more time on marketing activities than I cared for

While my prototype involved course development, I could extrapolate these problems to any form of solo business whether it be a micro SaaS, launching an app or similar.

This isn’t to say that none of these are solvable problems. For example, platforms like Udemy reduce the amount of time I would need to spend on marketing but they also further limit business upside. In the end I concluded that these problems might be tolerated by some but I found them to be unacceptable for myself.

Of course I reconsidered what problems I would be choosing if I went any of the other routes I considered too. Staying where I was would keep me in my meaning crisis and I expected a different company would do the same or even worse.

A New Option: The Indie Cooperative

As I dwelled on the dubious set of choices in front of me, I connected with some old friends who introduced me to a brand new idea. An idea that could pull me out of crisis and also presented the right trade-offs for my next career move.

I was “Going Indie” as the title of this post forecasted but not on my own. I joined a cooperative with other senior-level independent developers, designers and creatives who value the same things I do. Meaningful work, creative freedom, financial independence and so many other things that are difficult if not impossible to find on other career paths.

IndieDAO addressed so many of the problems I previously listed that I laughed out loud when I wrote it all down. The rich, vibrant community makes it difficult to be lonely. Innovative compensation models open the door for new forms of financial upside. I'm not 100% dependent on myself - I have others that I can lean on for advice and support. My only long-term commitments are to myself and to those I care about in the community. I’m not locked into any one product, project or industry - I work on new projects with new people every few months. And I choose the balance of how much time I want to spend on marketing and outreach for my personal brand and also for the shared brand. I enjoy producing content, attending conferences and networking but not all the time, just when it’s energizing.

I would be lying if I told you this new working model didn’t come with its own set of unique problems. Every choice is a selection of problems after all. Scheduling projects can be a challenge, especially when it comes to long term vacation planning. That exciting project you really want to be on might just conflict with that trip you were planning. Demand goes up and down with the market so project flow is difficult to predict. I need manage my own LLC, which means additional accounting and tax overhead.

In the end, the goal isn’t to make choices with zero problems. The goal is to make choices that have problems you can live with - where the benefits significantly outweigh the problems.

I concluded for myself that the IndieDAO cooperative was the right choice for me and over one year in, I’m not looking back. What feels really great is that this isn’t a stepping stone towards something else, it is the destination. From here I can continuously grow and progress in my creativity, my craft and my financial independence. And I’m not alone - others will help me along the way and I will help them. Cooperatives are positively different.