After two decades in corporate technology leadership, I'm now in my own career transition—building a fractional CTO practice and executive coaching business. Here's what I've learned about navigating major professional transitions, especially for accomplished executives who feel stuck despite their success.
We celebrate promotions, new roles, and career milestones. But we rarely talk about the messy middle of transition—when you know something needs to change but aren't sure what comes next.
The pattern I see repeatedly:
This isn't a crisis. It's a recalibration.
For years, I was "the technology executive at Deloitte working with state agencies." Shifting to "independent fractional CTO and coach" required more than updating my LinkedIn profile.
What helped:
The trap: Rushing to declare your new identity before you've lived into it. Give yourself space to experiment.
Initially, I worried that 20 years in corporate consulting might not translate to independent work. Wrong.
The reality:
Reframe: You're not leaving your expertise behind. You're applying it differently.
I spent months anxious about the transition until I got crystal clear on finances:
What changed: Once I had numbers instead of vague fears, decision-making became straightforward. I could evaluate opportunities rationally rather than emotionally.
If you're in transition or contemplating one, these questions have been most valuable:
Clarity Questions:
Reality-Check Questions:
The success trap: You've been rewarded for certainty, decisiveness, and having answers. Transition requires comfort with ambiguity and experimentation.
The expertise paradox: Your deep expertise in one domain doesn't automatically transfer. You're simultaneously expert and beginner.
The identity question: If you're not [previous title], who are you? This isn't philosophical—it's practical. How do you introduce yourself at a networking event?
The network challenge: Your professional network may be tied to your previous role. Building a new network takes intentional effort.
Start conversations before you're ready. I waited too long to talk about what I was considering. Early conversations create possibilities you can't imagine alone.
Test small. Don't quit your job to start a business. Start the business while employed—even if just evenings and weekends. Learn what works before making the leap.
Find guides who've made similar transitions. Not mentors in your old field, but people who've navigated similar transitions. They understand the emotional terrain.
Financial clarity precedes career clarity. Get your numbers sorted first. It removes anxiety and enables clear thinking.
Your transition timeline is yours alone. Some people make bold leaps. Others (like me) make gradual pivots. Neither is superior. Match your approach to your circumstances and risk tolerance.
The most surprising discovery? The skills I most value weren't technical—they were the ability to:
These transfer everywhere. So do yours.
I work with executives navigating career transitions through one-on-one coaching. If you're feeling stuck despite your success, let's talk.
This post reflects my personal journey of transitioning from corporate technology executive to independent fractional CTO and coach. Your journey will be different, but perhaps some patterns resonate.