“I will quit my job and start freelancing”, I told my friend over coffee, and as soon as I said it out loud, I immediately felt my shoulders relax. Over the last few weeks, I had spent countless sleepless nights pondering that decision, weighing the need for stability on one side with the desire for a drastic change on the other. Once I had finally made the decision to resign and go solo, it felt like the worst part was over. After I told my manager the next day, that calm feeling became even stronger.

This was my third job in a year (hello, Berlin startup scene), and this wasn’t the right place for me. But I simply couldn’t do it again, the long application processes, the technical interviews, the we-won’t-be-moving-forward emails.

Was this the right time to go self-employed? Maybe not. I had no idea how to run a business and didn’t have a single client lined up. But I felt like I had no alternative, so I took a leap. The only thing that allowed me to do that without freaking out completely was that I had anticipated the fall before.

And does that even exist, the perfect time to start your solo business?

This is probably the concern I hear people express most often: “I have been thinking about doing my own thing but now is not the right time.” I get it, among all the uncertainties that show up when going self-employed, time is measurable. It is easy to come up with a list of conditions that have to be fulfilled before you can take the leap: once you have saved x amount of money, once the loan for the house is approved, once you get the next promotion at work.

The one question almost no one seems to ask: what do I even want from this?

When weighing the decision, I also came up with a list of reasons for why now might not be the right time. If I resign now, will it look like I job-hopped too much? Shouldn’t I move into a new apartment first while I still have stable pay cheques to impress landlords? And the economy, isn’t it in the worst state ever right now? Shouldn’t I wait for the tech job market to become more steady again?

It is tempting to hide behind the timing question and use it as an excuse to never start, because there will always be one more milestone to reach that would make it easier to jump.

I was craving more freedom and flexibility in how I structure my work. I wanted to be able to go to the gym in the middle of the day, escape Berlin winters, and not spend hours and hours in all-hands meetings discussing OKRs and KPIs. Freelancing suddenly didn’t feel like an abstract thought of something I might do in the future, it almost started to feel like something I had to try, and I had to try it right then and there.

Once I had made the decision to give it a go, I didn’t try to find the perfect time to do it, I calculated how hard the fall could be if I jumped right now. I didn’t fully know what I was jumping towards, but estimating the fall gave me a few years to figure out where I might want to land.

I had no clue what I was doing, no clients lined up. If this failed terribly and I’d never find a paying client, would I be able to recover from that? In my case, the answer was yes, but it came from a place of privilege.

My cost of living was relatively low, I wasn’t financially responsible for anyone but myself, I had no mortgage to pay off. On top of that, working in the tech industry for years before I took this step allowed me to save enough money that I could pay my bills for a while even without any income, and it meant I had built a decent professional network of people who could vouch for my work.

So for me, the answer was very clear: I want to do this and it won’t ruin me if I fail. But the risk will be different for you and every other person out there. A software engineer and father sent me a DM at some point asking for tips on how to start freelancing. He was the sole provider for a family of five, additionally sent money back home to his family of origin, had a mortgage, and no significant savings. Just listening to his setup made me anxious.

For him, the fall could be much harder and mean that he couldn’t provide for the people who he loves. Freelancing might not have created more flexibility but rather reduced it. While there might not ever be the perfect time to go freelance, sometimes there are indicators that the fall would be too hard.

Three years into freelancing, I still can’t claim that I have found what I was looking for. My ideal Tuesday would include waking up without an alarm, and then spending my day reading and writing and thinking. I’m quite far away from that, and I sometimes feel trapped in a net of client meetings, deadlines, Slack messages, and admin tasks. But I have gained more freedom compared to being employed, and I can slowly work towards making my ideal Tuesday happen. It’s a steady and gradual process, not a drastic change.

I found it impossible to answer the question of whether it is the right time to go freelance, or rather, the answer was always no and always would be no. But when I swapped the question and looked instead at how hard I could possibly fall, I found that the worst-case scenario would not ruin me, and that I was excited about what a random Tuesday could look like on the other side. And those two things in combination made the leap not only worth it for me, but almost inevitable.

“Now is not the right time” - if that sentence sounds familiar to you, is that actually what you mean?

I have been binge-listening to the SOLVED Podcast with Mark Manson. I can particularly recommend the episode on anxiety. (Bastian, if you’re reading this, many thanks for the recommendation.)

low noise dashboard. issue #02 // 45 subscribers // struggling with EU data compliance stuff (don’t sue me pls).
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