Dear Dorothy,
I never imagined I would be writing in, but here I am. I’ve worked incredibly hard over the years to get where I am professionally, I’ve ticked every box. Promotions, accolades, financial stability… all of it. On paper, I’m winning.
But lately, I find myself feeling more isolated than ever. Friends don’t quite relate anymore. My family assumes I’ve “made it” and don’t check in as often. At work, I’m the boss; respected, yes but not confided in or truly seen.
I find myself asking: is this what success is meant to feel like? Why does it feel so empty? I feel guilty even saying it out loud. Any advice?
— Lisa
Dear Lisa,
Thank you for writing. What you’re feeling is more common than you might think, even if it’s not often said aloud.
Success can be a double-edged sword. While it brings recognition, responsibility, and rewards, it also comes with distance, sometimes emotional, and sometimes social. People may admire you from afar but forget that you’re still human, still craving connection and vulnerability like anyone else.
First, know that your feelings are valid. You’re not ungrateful, nor are you broken. You’re simply at a point where outer success is outpacing inner fulfilment.
Here are a few thoughts to sit with:
-
Connection needs intention. At higher levels, the spontaneous connection becomes rarer. That doesn’t mean it’s impossible, but it does mean you may need to be more deliberate. Seek out peers who are also navigating leadership: mentorship circles, masterminds, or even therapy can offer safe spaces where you’re not “the boss,” just a person.
-
Re-evaluate your circle. Friendships evolve, but they shouldn’t evaporate. If you’re craving deeper connections, reach out not with updates on your accomplishments, but with honesty about where your heart is.
-
Find joy beyond the job. Sometimes our identity becomes so entangled with our work that we forget who we are outside it. Reconnect with passions, hobbies, and even mischief, something that doesn’t need to be monetised or measured.
-
Speak your truth. You’ve spent years being strong and steering the ship. It’s okay to let your guard down. Whether it’s a trusted friend or a coach, share this version of your story. It might surprise you how many people have felt the same.
Loneliness doesn’t mean you’re failing, it means you’re human. And while the top might feel chilly at times, it doesn’t have to stay that way. You have the power, and now the awareness, to invite warmth back in.
With kindness,
Dorothy