Part 1:
In 2016, I was falling out of love with a career I once dreamed of - advertising. Folks in a similar situation would often jump off to the client side, or media. Neither appealed to me. I jumped off to - of all things - events. The company behind the music festival I'd attended for so long, the NH7 Weekender, asked if I'd be interested in joining them. It was a tough choice! I may have had my issues working in an agency, but it was safe, I was moving up (just been promoted to AVP), and good at it. Events would mean something totally new and something I had no experience in - a possibly risky move at 32. But dang it felt exciting. I took the leap and had an amazing three years. Till...
Part 2:
Three years later, I felt like I hit another ceiling and was wondering what I could do next. I felt the pull to go solo. I'd already done some on-and-off freelance work: cartooning, writing features, even some marketing stuff... But to do it full-time? That felt risky, and exciting. That combination worked well before. Some sagacious advice from friends (and some beer) later, the decision was made. I became a freelancer. The experiment worked well enough for my wife to join me two years later, and we formed Rough Paper Creative - still fiercely two-person, still taking on projects of our choosing, working how we like.
So two successful pivots. Along the way, there have been some mini-pivots (I became an adjunct faculty at a university for a year, and then gave that up - I guess combined those could count as a whole pivot).
Making the pivots work
I've always got questions on how I managed to make these pivots work - whether it was friends, students, or in interviews (like this one I did with Amit Varma, or this one with CTQ Compounds). Here are three things that helped me.
Having a safety net (or a fallback option)
It’s useful to think through the worst case scenario - what if this pivot doesn’t work - and plan accordingly. A safety net could come in many forms. I had some savings, the cushion of a supportive spouse’s salary, and enough of a reputation where I could go back to my earlier job. I’m not saying this to show off - if anything, I want to acknowledge my privilege - but I think reckless pivoting can be disastrous if things go south.
Setting medium-term targets and sticking to them
The first few months of a pivot are always exciting. The long-term is too difficult to predict. I ignored both. It was more important for me to set realistic medium-term goals. In the first case, it was whether I was good at a completely new job (I was decent), and in the second case, it was if I could match my last year’s salary (overshot by 50%). Having clarity on those helped me work towards something more tangible than vibes.
Hunkering down and getting it done
No getting around it. Making pivoting work is hard work - you have to do things you thought were below your pay grade, or do tasks you didn’t think you’d need to (it’s funny how freelancing can make you gain immense respect for your erstwhile HR and finance departments). Yep, just gotta get it done. I worked my arse off.
Now that I’ve told you what worked for me, here are…
Three pieces of advice I would give anyone considering a pivot at any level
The pull should be stronger than the push
Never run away from a bad job or career. Run towards something you find more interesting. I think the hate of something (or someone!) can make you blind. Ask yourself - is the thing you’re considering truly pulling you?
Be aware of the downsides
Keep rose-tinted glasses away, and make a long list of cons. Whether it’s inconsistent or lower money, atrophying of certain skills, needing to learn new ones, having to be your own boss (not as romantic as it may seem), missing human contact, missing a potential ESOP sale… Consider everything and plan for the worst case.
Analyse if conditions are right for you to take the leap now
I mean this more from a YOU perspective than a market perspective. When I started working for myself, I knew I had a decent reputation among my network that would spread the word, AND some experience doing freelance work before. I think the latter is very important - you want to do a lot of groundwork to set your pivot up for success. Maybe it’s establishing the right contacts, maybe it’s learning a new tool, maybe it’s gaining some experience.
I hope these thoughts help you out. Of course, during Unstuck, we will be covering these in detail - and a whole lot more, to help you with pivots in your career, and life.