Career Uncertainty In Your Early Thirties


Comparison. Doubt. This way and that. 

Career is the one area of my life that's always felt a bit lacking or fuzzy. At my core, I'm a curious person. This curiosity can be an asset, but it also feels like it's held me back in some ways. 

10 years ago, I graduated from college, with a degree in Communications Studies. Between now and then, I've:

  • Worked on and won a congressional campaign in Kansas
  • Spent a year working on Capitol Hill
  • Ran by own business for four years, helping restaurants and small businesses with social media
  • Completed a life coaching program and coached clients for awhile
  • Got into the wine business, eventually becoming a wine buyer
  • Moved into the tech industry, where I learned the ropes of customer support, led a small team, and once again find myself doing customer support

I don't want to say I'm disappointed in myself, but I struggle with comparing my career-life with that of my close friends and acquaintances who are around my age. This is probably common and makes me human. It still feels unsettling.

Most of them seem so senior in what they do. They're making more money, going on trips, and appear to be more "established". They've stuck with one or similar industries, while I've weaved and meandered from one thing to the next.

On my down days, this wave of panic rises up, with thoughts of:

  • How will I pay for retirement?
  • Just pick something and stick with it
  • Who will hire you with this work history?
  • Are you qualified for anything other than customer support?
  • You don't have "hard skills", like a graphic designer or web developer 
  • What can you even tell people when they ask what you do?

Those thoughts, mostly from my gremlin, seem convincing at times. Then there are the other voices that tell another story:

  • Josh, the variety of what you've done has equipped you with so many skills and talents
  • It's never too late to start over
  • You have a lot of talent and heart
  • There's so much possibility, even if you don't see it yet
  • Life is more than a career

Career often feels like the one puzzle in life that I can't quite solve. Do I have the right pieces? Am I missing some? Is it more organic and non-linear than a simple point A to point B?

Over the last two to three months, I've been exploring the world of HR (or People operations) and see a lot in the field that I resonate with. I'm trying to take steps to move in that direction, without any HR education or even entry-level experience. Reaching out to people in the industry has been helpful - getting advice, insight about the industry, and how I might be able to find my way into this field.

I'm uncertain, but hopeful. Afraid, but eager to find my way. It's tough to say what my next chapter looks like. Another twist. Another turn. Yet there's always that fear, knocking in the back of my brain. Perhaps that's just part of the journey.