I did a major career review during 2023. I’m sharing it now because:

1. I think it’s a good case study for iterated depth decision-making in general and reevaluating your career in particular, and 

2. I want to let you know about my exciting plans! I’m doing the Tarbell Fellowship for early-career journalists for the next nine months. I’m excited to dive in and see if AI journalism is a good path for me long-term. I’ll still be doing coaching, but my availability will be more limited. 

Some career decisions are easy. There’s a clear best option. 

Many are not easy. Where are you a good fit? What would you be best at? What work is most important? These questions can feel baffling. How do you even start getting the information to make these decisions well? 

Do you wish you could just look at how successful people made their decisions? What made them confident in their plans?

Well, here you can. Here are 10+ real stories of career decisions. Each story is a real account from a real person. You can see what works -- and what doesn’t. 

In the spirit of growth and self-improvement, I recently attempted to apply Ericsson’s principles of deliberate practice to my own growth goal: speeding up my writing. If you're unfamiliar with the minutia of Ericsson's methods, don't worry, I was in the same boat — and hence my initial goal had substantial room for improvement. This is the story of how I used to deliberate practice principles to workshop my growth goal.

Doctors, painters, writers, and composers seem to get worse at their jobs after a couple of extra decades of experience.

What’s going on here?

I was diagnosed with attention deficit hyperactivity disorder (ADHD) last winter. 

I’m a productivity coach who frequently works with people who have ADHD. I’d studied diagnostic questionnaires and read about the official symptoms of ADHD.  

I’ve also been struggling with those symptoms for decades. I was unable to consistently focus on demand, felt constantly tired, and often needed to force myself to get started on my projects. Yet I never seriously considered that I might have ADHD. 

Why not?

I felt scared just thinking about the ideas, and terrified at the thought of telling others I was attempting them. What if I tried and failed? Or just decided it wasn’t worth it after all? Would they write me off as a failure? 

Those fears were my wake up call. I couldn’t really explore career options if just thinking about them felt scary. So I scheduled some sessions with a cognitive behavioral therapy (CBT) therapist and started Overcoming Perfectionism by Roz Shafran (a CBT workbook). Here you can see what that process looked like.