How I kept myself accountable as a founder in the first year

Many of us dream of being free to work on our terms, choose our work hours, and decide what we work on.

When I quit my job to start Prodsight, that become an instant reality for me. I no longer had a boss or colleagues to report to, I could decide when I worked, and there certainly wasn’t anyone telling me what I should or shouldn’t do.

Except it didn’t feel as good as I expected. Certainly not as “freeing” as I imagined going in.

Instead, I was met with a crippling sensation of anxiety, guilt, and fear. I was anxious about not doing the “right” things or not fast enough to advance my startup. When I got stuck in an unproductive state, I would feel guilty for wasting the time and the opportunity in front of me. And on the most gloomy days, I would fear that the whole thing would fail, burn through my savings, and be left with nothing to show.

I was so focused on the financial part of surviving the startup journey that I forgot to figure out an even more important aspect, my psychology.

I craved structure

I realized that I got used to the structure of having a set workplace to go to, set hours, a group of people to interact with every day, and a source of direction from my manager.

As I’d kiss my wife goodbye as she went to work, I’d have the entire day to work on my new startup. But there was no place to go to, no set hours, or anyone to interact with. I was entirely on my own.

I was craving the structure that my job provided and that I was taking for granted.

Rebuilding some form of sanity meant re-establishing the environment that made me productive as an employee:

• Workspace

• Work hours

• Accountability

Workspace

After the COVID-19 pandemic forced us all to become remote-working experts, it is now my most productive and preferred work mode. However, when I started Prodsight in 2017, five days in the office was the defacto way of working and something I was used to. So when I no longer had an office to go to or anyone to talk to all day (I was a solo founder), staying home to work on my startup felt incredibly isolating.

The natural temptation to procrastinate was unbearable. Instead of trying to work on the “hard” things of validating my business idea, building prototypes, or making plans, all I could think of was making another sandwich, another coffee, or watching just one more episode of my favorite Netflix show. All of that is with a side of guilt and self-loathing.

I just had to get out of the house!

Since I was bootstrapping, I opted for the cheapest option of working from a nearby coffee shop. Getting out of my flat gave me bursts of productivity that I needed to make progress. The psychology was that since I have gone through the effort of leaving home and the expense of buying a coffee (a luxury at the time), I now must do something productive to make it all worthwhile. It worked. I worked.

Eventually, my back started hurting from days of sitting on hard coffee shop benches hunched over my laptop, and I decided to get a co-working pass at a nearby co-working space.

My first co-working space

Work hours

Technically I could work on my startup whenever I wanted. There was no one to tell me when I should be working.

However, it made sense for me to set regular working hours for my sanity. I decided to align my hours to my wife’s, which meant a standard Monday to Friday, 9 am to 5 pm.

Working this corporate schedule meant a return to a routine, giving me some sense of normality to the chaos of the early days of a startup. I would try to make as much progress as possible during the workday, knowing that I would l have to “clock out” at the end of the day. This put a rigid boundary on how I viewed my workload and minimized procrastination. I could no longer push the work into the evening or weekend, at least in theory. In practice, I sometimes worked late evenings and weekends to get things done.

The other benefit was that I could spend time with my wife once she returned from work without feeling guilty that I hadn’t done enough.

Accountability

Even in jobs where you have a lot of freedom, there is always someone you are accountable to. Whether it’s your boss, your colleagues, customers, or partners, there is always a motivation to deliver or else.

In the early days of a startup, there is none of that! You are your own boss, you haven’t hired any employees, and you don’t yet have any customers or partners because you don’t have anything to sell.

We are conditioned to do things for others, whether consciously or subconsciously. Initially, I found it very difficult to be accountable to myself. I needed someone to validate what I was doing. I wanted someone to keep me accountable.

For most startups, I suspect this would be solved by having a co-founder, but I was flying solo.

I contacted my good friend and startup founder Martin Lind and asked him to be my accountability partner. We would meet in a cafe every two weeks, and I would have to report to him on what progress I made on my startup, what challenges I encountered, and what next steps I wanted to commit to.

The knowledge of the constantly looming meeting with Martin meant that I always had the incentive to make progress with my startup and complete the action points so I would have something meaningful to share with him. I knew deep down that if I failed to keep up, I would lose his trust, and our “arrangement” would fall apart.

He was incredibly patient and generous with his time and feedback. I am forever grateful for that. Martin’s input was so valuable that I asked him to join our board of directors and gave him stock options.

Once I hired employees, raised investment, and secured early customers, I no longer needed to fabricate accountability. The startup suddenly felt very real, and I felt an immense sense of accountability to the people I pulled into the journey for me. The big challenge was getting to that point.

Closing thoughts

Surviving startups is as much a psychological puzzle for founders as it is about skills, knowledge, or finance. I surprised myself by craving things I was seemingly running away from, like fixed workspace, consistent work hours, and external accountability.

It might be different things for different founders, but staying productive in the early days is critical as you are the only engine keeping things going. The day you stop, the whole thing falls apart.