How Regret Distorted My Career Path

For a long time, I carried the weight of a major regret: getting my Master’s degree in a subject that would never translate easily into a “real job.”

In the hazy clusterf*ck that was my post-grad job search, I berated myself constantly for choosing to spend close to $80,000 on a degree in Conflict and Dispute Resolution that didn’t seem to be getting me anywhere.

I’d launch into thoughts like “How could I be so foolish?” or “I’m so impractical,” or the most painful one: “I wasted all that time and money and am no better for it.”

I hear sentiments like this from clients all the time - pain associated with the belief that they’ve wasted the best part of their careers, a ton of money, or even their entire lives in the pursuit of “the wrong thing.”

Even though I could rationally justify getting my Master’s degree in conflict resolution and wouldn’t change a thing because I met my sweet husband in the program, the painful thoughts still haunted me. At their core was a story about shame - a story that said I’d made a huge mistake and couldn’t be trusted to navigate my life in the future.

If I was willing to blow all that money and “waste my time,” how could I be trusted to choose my next steps wisely?

So not being willing to trust myself, I handed over my authority to the “experts,” who all told me to be practical. To start over in an entry-level role. To bide my time and work my way up the totem pole, hating it all the way, but with the carrot of prestige and retirement hanging ahead of me.

And I tried this approach. I really did. I spent months applying for jobs I was over-qualified for, under-qualified for, jobs I knew I didn’t want but thought I should take, and everything in-between.

All the while, the belief that I couldn’t trust myself to make big career decisions kept operating under the surface, compelling me to pursue a path that wasn’t mine.

When I finally became aware of this belief, I started to see its tentacles all over my present situation. It would convince me that I didn’t know the best way to answer interview questions, that I needed to keep revising my resume according to the latest article I read, that I couldn’t trust my intuition when someone I was networking with seemed “off.”

Once I could see how this story of regret and distrust was impacting my choices, I had to decide what I wanted to do with it. I ultimately chose to discard it and believe instead that everything is progress, to be grateful for the opportunity to learn and meet some wonderful people, and to trust that I could absolutely find my own way forward.

I had to recommit to this choice about ten times every day and tell myself again and again, “I trust myself to find my own way forward.”

The fact is, my regretful thoughts and the self-hatred they embodied weren’t really me. I believe that each of us has a part of us that buys into beliefs like these in order to keep us “safe” and socially in line, and another part of us that knows our own truth. Some people call these parts of us the “ego” and the “soul.”

My ego cared about appearing like I had it together, like I knew what I was doing, and if that meant feeling regret and shame over my choices in the past, so be it. My ego told me that I couldn’t be trusted.

But my soul, or intuition, helped me see that those thoughts were anchored in beliefs that weren’t truly mine. When I got quiet and centered enough, I felt a wave of truth and trust in myself, which I knew to be more real than the cycle of pain and regret I’d been in.

If you feel distressed about your career - if it keeps you up at night, if there’s tightness in your body when you think about it, or if you’re just too afraid to really explore your unhappiness - I’d encourage you to ask yourself this question:

Do I trust myself to find the path that’s right for me?

If the answer is ‘yes’, hold your heart and let the glow of this belief fill you up and move you into the next best action.

If the answer is ‘no’, like it would have been for me, I encourage you to spend some time introspecting on whether or not you’re carrying regrets that are preventing you from seeing yourself clearly.

Is there something that happened in your career or education - some choice you made - that’s causing you pain and self-doubt?

Try to identify what it is and ask yourself if that self-doubt has caused you to hand over the authority over your career to other people. Has it caused you to implicitly give your spouse, parents, friends, experts, or peers the authority to dictate what you should do in your worklife? And, more importantly, are you okay with giving up your authority?

In his book Walking on Water, Derrick Jensen writes, “If we wish to make different choices we must smash the frames that constrain us. We must, if we care about our own lives, and if we care about the life of the planet, begin to remember how to think critically, how to think for ourselves.”

It took me a while to smash this constraining frame, and it still shows up sometimes when I feel like I’ve failed or lost my way. When I get to that place, I have to get quiet again and really check in with the part of me that knows what I need - the part of me that doesn’t use shame and fear as motivation, but that draws me out with kindness.

If I hadn’t come to terms with the pain and distrust associated with my decision to go to graduate school, I’d probably be working in a job I hated, hustling to show everyone how successful and corporate I was. I’d never have trusted myself enough to pursue a path that really felt like mine.

I won’t leave you with a five-step plan for how to learn to think and feel for yourself (because there is no such plan), but I will implore you to do one thing: trust yourself. Even if it feels like you can’t or you shouldn’t.

Trust your intuition.

Trust your soul.

Trust your self.