New year, new thinking: What to do when you’re stuck in a rut

New Year’s is a good time to think about change.

As I think back on all the biggest opportunities and shifts I have made in my career, they all have these things in common: I was feeling stuck and bored. Something was tickling the back of my imagination. I moved toward it. And eventually, I redefined myself around it.

Three years into the Ph.D. program in math at MIT, I was feeling frustrated. I’d passed all the exams but a thesis was not in sight. So I quit and became a technical writer at Software Arts, writing about mathematical software. All my math professors thought I was insane. I had no idea at the time that I was starting a 35-year career in business.

Several jobs later, I was running the production department for a startup publishing company. I had six or eight people working for me, and we had pioneered a new way of writing textbooks which delivered finished books about 6 months faster than the competition. Since these were books about how to use software, that made a difference. But it was a job about schedules and management, and I’d solved all the problems — what was left was operations. So I told my boss that I wanted to hire my replacement and switch over to the company’s fledgling educational CD-ROM business. That business eventually went bust, but that job was the beginning of 25 years of learning about and analyzing interactive media.

After ten years as a Forrester Research analyst, I’d written about the television industry and the music industry and launched a survey business. But I felt there was nothing left to prove as an analyst. So I prepared to quit and become an author. (Luckily for me, the CEO, George Colony, decided he would rather keep me as an author working for him than see me go.) That was the beginning of my career as an author, which has yielded a decade of work with four books so far.

After 20 years as an analyst and author at Forrester, I took a severance package and launched myself as a sole proprietor. I wrote a book about writing. And now I have a successful business helping companies with writing and authors with books.

How to get out of the rut and do something better

Are you stuck? Based on my experience, this is what you should do:

• Keep at it. Stick with what you can as long as you can. I didn’t quit these jobs that were boring me precipitously. You don’t want to be one of those people who can’t stick with anything for long, and it’s always easier to keep improving what you’re doing than to change tracks. There’s a great little book on how to make these decisions: Seth Godin’s The Dip.
• Consider possible paths connected to what you’re doing. Talk to people. Do research. And figure out what sort of pivot might make sense for you. Dream like a professional. In my experience, this process takes months, sometimes years. But it’s something you should apply yourself to diligently, so you know you are making a good decision.
• Learn as much as you can. Take classes. Go to conferences. Pursue side projects. This is not only to develop the skills you need to do something different, but to figure out if you will actually like it.
• When you decide to make a move, prepare. When I left graduate school, I was too young and inexperienced to understand this. But for all the other changes I made, I had prepared. I spoke with my family. I prepared for possible financial disruption. I hedged the risk as much as I could.

Dreaming of something better — and being frustrated with what you’re doing now — sounds both urgent and fruitless. In fact, it’s a process. If you pursue it faithfully, you can get ahead without destroying everything you’ve built already.

Why I’m thinking about this now

I’ll be doing something different soon. I’ll explain it to you all tomorrow.