Professionally Lost: The Dark Days of Making a Career Shift

I’m 33 and it feels too late to start over.

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The window for choosing a specific profession, pathway, or “career” is narrowing. Time’s running out. I’m missing my chance to carve out a unique path for myself. Even though I intellectually know many people make career leaps and have breakthroughs later in life, lately, I’ve felt more like this:

Friends I know are moving up the ladder of their respective industries, having stayed in the same or similar work since their early to mid twenties. Right now, I’m in a role (of my own choosing) that feels so below my capabilities, yet moving up and into another field feels utterly impossible at times.

I am in a state of panic.

This may come across as melodramatic and without a larger perspective of how much “work life” I likely have left. I’m incredibly grateful to work at a company where people are open and willing to share their wisdom and path to get to where they are. That’s not the case in many workplaces.

That said, the voices of shame are real:

  • You really missed the boat on this career thing. Good luck with that!
  • Wow, you’ll probably still be in an entry level job at 40
  • Who do you think you are to try and start in a new field?
  • You have to pay for your lack of career planning and refusal to stick with one path.
  • You aren’t focused. Focused people pick one thing and often find success.

I understand even getting to consider what career I actually want is an incredible privilege.

At the same time, I feel incredibly embarrassed, unaccomplished, and honestly so small to find myself in this place at age 33.

I’ve been more like this lately:

credit: giphy

Over the last year, I’ve been researching and exploring various possible paths:

  • HR
  • UX Design
  • Some sort of role that involves facilitation/coaching/writing

I’ve read some great books, particularly Reinventing You, With a New Preface: Define Your Brand, Imagine Your Future by Dorie Clark and Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett and Dave Evans.

Part of me longs for someone who is professionally successful to look at my past and say, “Josh, your last 10 years of work isn’t a waste of time or energy. You have real skills, talents, and strengths that serve the world. You have value. You matter.”

It’s been a challenge to give myself that affirmation lately. Instead of abundance and rich experiences, all I see are gaping holes and unfocused moves from one industry to the next.

While other areas of my life feel so rich and full of meaning, “career” is the one area of life that feels painful and chaotic. Like a work of art that never fully comes together — a mess that never gets cleaned up.

The other day, I was joking with a friend about how nice would it be to simply tell others — oh, I’m a doctor or I’m a lawyer. I’m ENTER JOB TITLE.

That’s clear-cut. Easy to understand. Little more needs to be said.

Instead, myself (and many others I know) are career wanderers, having a mish-mash of experiences that are often seen as aimlessness by recruiters and successful professionals.

Where the hell do people like us fit in?! The professional, “work world” doesn’t seem designed for people like us. Even though I read articles about how companies desire people with a wide breadth of knowledge and experiences, those seem more like disconnected think pieces, rather than actual practices of companies today.

When it comes to the nuts and bolts of job searching, companies are really looking for experience and expertise.

A story I keep telling myself is that businesses don’t want to hire “jack-of-all-trades” or multipotentialites — both ways of being I’ve tried to embrace with pride. Yet when I look across roles and opportunities, even in NYC, the work world seems to look for people who invest in one particular path.

I realize this post is part bitch-fest, part rant of hopelessness. It’s not that I have zero faith I’ll be able to find my next career chapter. It’s that this is where I’m really at right now.

Feeling hopeless, sad, and overwhelmed about what next steps to take. As I type, there’s a tense, fist-clenched feeling in my chest and my energy level has been low for a few days.

I also know that I won’t always feel this way, because I haven’t always felt this way about making a career transition. Some days I feel empowered and that progress was made. Whether that was due to a conversation I had with someone in a field I’m interested in or an e-learning course that helped narrow down what I don’t want to do next.

My hope is this post will speak to others who are thinking about or in the midst of figuring out “what’s next”. It is work. It may be rewarding once you get to the other side. But there may also be dark days of discouragement and overwhelm.

I’m not sure I’m handling these dark days gracefully, but hopefully knowing that those days will come and that you’re not alone will help you get through your own career reinvention.

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Josh Hersh

Seeker. Writer. Hot cocoa entrepreneur. Cat dad. Musings about spirituality, ecology, and more. joshhersh.com