The biggest career mistake I see in leaders isn’t failure. It’s playing it safe.
What bold change would you make today, if only you knew you’d have no regrets tomorrow?
In a turbulent world, it’s easy to cling to the safety of what we know instead of jumping into the unknown. We avoid the immediate regret of losing of what we have, especially if it is bound to our identity. But if we’re stagnating in our current role, that safety can vanish, and our future self will really regret that we stayed.
I joined IBM out of university. After two decades, I felt stuck. I pivoted to different roles and started coaching and teaching as side gigs within the organization, but it wasn’t enough. If I wanted to grow, I either needed to move to another city or get on a plane too often on Monday morning.
Still, I worried that I’d regret leaving an innovative company, great people, and a competitive salary. Then one day I realized that future me would regret settling instead of exploring what else might be out there.
When I turned in my badge, I had no new job lined up nor even a current CV. Instead of fear or regret, I felt relief. I was finally committed to change. I slowed down to reflect on my goals, spend time learning, and develop course material that I now teach.
Besides a complete lack of regret, the break brought perspective on my time at IBM. I appreciated what I had learned, the people I worked with and what we had accomplished together. A few months later I started looking for another role.
The big insight: our future selves will view our situation very differently from our current selves. My entire outlook changed the day I left.
So, what bold change would you make today, if only you knew you’d have no regrets tomorrow?
If you’re clinging, or stagnating, or settling, message me. As a coach, I can help connect you with your future self to see their perspective, and I’m willing to take on two pro bono clients this month.
