Why Am I Still Dealing with This? 5 Career Challenges That Refuse to Go Away
These aren’t one-time hurdles. They’re the recurring patterns that slow us down, drain our energy, and keep us stuck. Let’s name them—and start moving through them, one bold step at a time.
I’ve been thinking about you.
Not in a creepy way. It’s more in a “you’re one of the amazing humans I’ve had the privilege to coach or work closely with” kind of way.
Lately, I’ve been writing a lot about impact—how we chase it, lose it, and try to get it back. And honestly? You inspired that.
So, I did what I always do when I need clarity: I zoomed out. I revisited notes from hundreds of coaching conversations over the past few years and started seeing five patterns emerge. The same blockers. The same stuck points. The same questions.
Self-doubt and invisible confidence killers
Overthinking and fear of risk
Burnout and the sprint-to-nowhere
Presence and persuasion
Wanting more but not sure how to get there
What I noticed is that these are perennial challenges. Think about flowers for a sec. Annuals are the loud, urgent crises that flare up and fade. But perennials? Those are the deeper patterns like self-doubt, overthinking, or the fear of speaking up that keep resurfacing.
They’re not one-and-done problems. They’re ongoing growth areas.
The most successful leaders I coach don’t try to “fix” these. They get better at recognizing them, navigating them, and growing through them season after season.
Here’s the good news: these blocks are totally normal. And better yet? They’re move-through-able.
That’s why I’m launching something new: The Core Career Challenges—a short, 5-email series you’re already on the list to receive.
In each note over the next couple of weeks, I’ll share:
One perspective shift or new way to see the challenge
Two stories or stats to make it real
Three quick ways to apply it
(Some days, I may toss in a tool or video if inspiration strikes.)
This is a quiet launch just for my inner circle- mid-career pros like you who care deeply, work hard, and aren’t done yet.
No pressure to reply. But if something resonates? I’d love to hear from you. And if you know someone who needs this too? Forward it.
More to come soon and possibly a live session down the line.
Thanks again for being part of my journey. Coaching you has shaped mine in ways you may not even realize.
Let’s keep going one bold move at a time.
With gratitude,
Robin