Freelancing and Back in One Year - A Retrospective - Part 2

In my last post about why I quit freelancing, I explained my initial motivation for initially going freelance. In short, the two points were

  1. More freedom
  2. More technical work

Don't ask me why, but when I started freelancing I somehow expected to automagically get development projects, that would satisfy point 2 on above list. It took me quite some time to realize that it's not going to happen. Especially not as long as I continue selling myself as a consultant/teamlead/coach-hybrid, the things and roles I previously worked in, and which I knew I can comfortably fulfill.

Looking back, I really don't know what I was thinking. In interviews with potential clients I always tried to sell the “leadership” part of my previous jobs and then wondered a bit, when they offered me consulting jobs instead of development jobs.

As I said it took me a while to figure out, that it was my fault and that I was the only one who can change it. But when I got that, when it clicked, man, was I relieved.
That exhilarating moment, when you realize, you're the one in charge, and nobody can stop you from trying out new things. No boss, no company strategy. In fact I was the “company” and I defined the strategy.

What helped me get there (having that Eureka moment) were the regular, if infrequent, meetings with a business coach that I granted myself from the beginning (not the least because it was heavily subsidized by a government funded agency). Those meetings, though they were initially focused on writing a business plan for a (SaaS) product I had in mind, broadened my horizon in unexpected ways and left me with the realization that I could do nearly everything (business-wise). Sounds corny and obvious, but really blew my mind back then.

But while those coachings helped me, they were not enough for me to connect the dots.
I needed several more months to notice that I was getting the wrong clients and projects, or rather that I was working on projects that only fulfilled one of my two goals for going freelance. And I didn't really have an idea on how to change that.

In Retrospect

All this happened around end of 2012, beginning of 2013, meaning I freelanced for ~9 months back then. End of the year seemed like the perfect time to take a step back and reflect on future directions. Looking back, my way of doing retrospective could've benefitted from a bit of formality (in the sense that I write down some things, compare alternatives etc), so maybe the word retrospective is a bit too much. What I was doing actually, was kicking around questions and ideas in my head for quite some time. And during this time two very good things happened.

  1. J.B. Rainsberger launched his My Agile Tutor service.
  2. I met the founders of vaamo (spoiler: I now work for vaamo).

I had some hour-long coaching sessions with J.B., and they totally blew my mind. I mean, t.o.t.a.l.l.y. He definitely knows how to ask questions and how to get you to a point where you believe you came up with all the action items on your own. Which is kind of important and useful, because I left every session not only with a slew of ideas, but also with very concrete things to do.
So basically he provided me with enough ideas and some more confidence to actually start shaping my freelancing business. I started working on those ideas and quickly saw first results such as having different conversations with my clients.

At the same time I started speaking with the founders of vaamo, as they were looking for someone to lead their technology efforts.
To make a long story short, I joined vaamo as the first employee in sometime in March 2013, while still finishing some work for my freelance clients, and switched to full-time in May 2013.

Why did I ditch freelancing?

Not even a year after starting it? As I said in the beginning and in my first post, I wanted freedom and technical work from freelancing. And vaamo looked like an opportunity that can provide me both and even a third aspect: Building and leading a team.
As it turns out I really enjoyed working “as a manager” in my previous jobs, and vaamo was an opportunity to build on what I learned in both fields, technology and people, and improve it.
And of course they had a vision for a product that really convinced me.

So joining vaamo really seemed like the perfect combo for me: Freedom of work in a young company, lots of technical work, building a team from the ground up and leading it.
And it actually turned out exactly as anticipated. I learned so much in the past 15 months, digging into so many new and interesting technical details, got to know so many great people, found wonderful people for an amazing team, which makes getting to work an everyday pleasure.

And, shameless plug: If you'd like to follow what I and my team are doing at vaamo, our tech blog and @VaamoTech on twitter are good places to do that.


If you're a freelancer or thinking about going freelance, I got a three recommendations:

  1. Think hard about what you want from it, why you're doing it ...
  2. ... and then define a strategy that fits you for achieving those goals.
  3. Get help and don't do everything on your own. Be it, that you form or join a collective of freelancers, that you join mailinglists where other, experienced freelancers mingle or that you seek support from coaches or similar people. Really, do it!