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#2640F

It’s been almost 6 months since I started in my current job and about a year and a half since I’ve returned to full time employment. On paper I’m in a good spot financially, carreer-wise and in work conditions. Nevertheless I’m stressed and unhappy most of the time. Today I want to explore why that is and maybe what I can do about it.

I have a pretty typical “high-functioning ADHD” work history. I started out in freelance photography, moving on to a couple of failed businesses with friends and finally freelance web development in my early twenties. My first job as an employee lasted five years, moving from customer support to product management at an SaaS company. I was contemplating quitting for close to a year when I was let go - burnout and a company restructuring left my position easily removed. I spent half a year blissfully coasting on my severance before joining a friend’s company running marketing and most of the software-related initiatives. Once that company started circling the drain I moved back to project management at a software agency, spending 8 months going from fired up to burned out and leaving. An unexpected windfall and savings allowed me to spend the next two years free. I dug deep into photography, completed photojournalism school and started freelancing in web development again. As resources started to run dry I started contracting as brodacast technician at a sports TV channel. After about half a year I took a full time IT admin job, then hopped to a BA role once my employer started sliding towards bancrupcy (again). The BA role was miserable from the start so I jumped ship once more, landing at my current employer leading their newly established software team.

Almost all of my full time roles started with excitement and high commitment then ended in fast and total burnout. Freelancing periods felt a lot better, but usually ended when my challenges with bringing in new business caught up with me, leaving my finances untenable. The exception is the TV gig, which wasn’t really freelance, limiting my income simply by the amount of work the station had available (plus the strain of working mostly nights and weekends didn’t help).

So let’s look at the patterns in all this.

Software jobs leave me struggling with the requirements of employment - set working hours, office presence, having to prioritize the formal framework over the substance of what I’m producing. They usually don’t provide much emotional fulfillment either, with the straightforward business mostly being in boring background services for giant corporate clients.

I do genuinely enjoy software however, and even while in dayjobs in the field I often try to find more exciting software projects to do on the side.

Freelancing lets me work with, rather than against my natural tendencies and allows me freedom to find excitement in how I solve a particular client problem. Being responsible for bringing in business however is immensely stressful for me. I’m generally uncomfortable with and unmotivated by all the business parts of running a business, so the burnout stems from having to force myself to do the things that bring in income, while not being very good at them either. This internal conflict tends to also taint the substance of what I do; after my first major period of freelance photography ended, I didn’t touch a camera for years.

The conclusion: I need the freedom of creativity and flexible working conditions of freelancing, but I also need the stable income and lack of business responsibilities of employment.

My current job is almost perfect on paper. I have flexible work hours, work mostly from home, I have some control over my and my teams workflows and approaches, I have new projects regularly to keep up excitement and a solid salary to allow me to not worry about finances day-to-day. So why am I not happy?

Even though in theory I have all this freedom and control, I still feel like I need to fulfill all the explicit and unspoken expectations of company politics, buorocracy and productivity ideals. Logging work time, being available any time my boss randomly schedules a call, jumping on every new task as if it’s life or death to complete - I feel my job’s in jeopardy if I’m not a good, obedient worker bee.

Objectively however I have the framework to treat this job as a freelance/consulting role without the sales and the uncertainty. I have more freedom and authority to shape things than in any previous role I’ve had. When I need to commit to a deadline, I can work following my natural rythm, working intensly in a couple days’s sprint. Just because everyone else around me works at a steady pace from start to deadline doesn’t force me to do the same. I can ignore a phone call and call back when I’m ready to, I can block out my calendar to prevent unexpected urgent meetings, I can work from cafes mixing photography and work during the day, I can take a day off when I’m low on energy without needing anyone’s permission. Like a freelancer, I only need to make sure I produce good work by the deadline. How I get there is, in practice, fully up to me.

So for my current situation this might be the way out of stress and burnout: realizing and keeping in mind the fact that I need to meet explicit expectations but not imagined ones. I can think of myself as a free agent, contracted to produce work rather than an employee required to act busy for the benefit of the boss.

A different aspect of what I am drawn to do is the content of the work. I feel strongly that some things are valuable for me and others aren’t. In art as well as technology I suffer from a lack of this value and have a stubborn urge to flip the table and go do something valuable, whatever may come.

But what do I mean when I feel something is valuable or not? What defines the things I feel I want to spend my life doing?
I have some thoughts on that:

Putting all this together I’m not sure where I land. The dream has always been to be in business for myself, fueled by excitement and making interesting, human scale things. I’ve spent over a decade returning to this dream again and again. It takes a different shape every time - an indie software studio, a SaaS business, photojournalism, being a full time artist, quirky IT services for cool organizations, the list is endless. Every iteration deadends however when I realize the idea needs more than motivation and excitement and creativity, it needs a business model and a source of new clients. That’s usually where I dejectedly close the notebook and relegate myself to trying to optimise the misery out of my current job for a few more months.