When your career no longer feels intentional

This week’s edition of Wishful Working was written by Alyssa Towns of Time Intentional (one of my favorite newsletters!).

I don’t know about you, but growing up, everyone around me encouraged me to:

1. Get good grades 

2. Go to college 

3. Get a good job 

4. Climb the (invisible yet ever-controlling) career ladder

Repeat step four until retirement. Cycle between steps three and four when you want to make more money or need a change, but stay within your lane of expertise because once you choose a career, you stick with it, right?

This is the traditional career path, one many have no issues with and are okay pursuing for various reasons — the funds to live the life they want, the perfectionism they’ve never shed, and the external validation they crave. 

But if you read Wishful Working, that might not be the route for you. 

And it’s okay, friend, because it isn’t the route for me either. 

Admittedly, I don’t recall ever believing you have to have the same career until you retire  because that’s not how my brain works. As a first-generation college student, I didn’t truly realize what I was signing up for when I was 18 years old. (Do any of us?) 

Don’t get me wrong, I am genuinely grateful for my education and the experience that shaped who I am today. I also appreciate every role I’ve ever held that contributed dollar signs to my bank account, no matter how unconventional the journey may have been. 

I don’t believe work should be your entire life, the core of your identity, or your sole motivation in life, but it damn well should feel intentional (and authentic to you). 

Some research suggests the average person will spend 90,000 hours at work over a lifetime. Or ‌⅓ of your lifetime. That’s a lot of hours and a lot of life. 

When our work life feels unintentional, outdated, or no longer a good fit, we often wish away those 90,000 hours, remaining in a constant state of misalignment and rarely showing up as our best selves. 

Before we address how to realign, there are a few important points about careers today worth noting:

• It’s 2025, and the working world changes on a nearly hourly basis (especially if you are a knowledge worker). It’s okay if your career looks different from someone else’s career in the 1980s. 

• Our lives change with age, which means our values can (and often do) evolve. It’s okay if work that once fit you well no longer aligns with who you are and what you value. 

• You’re allowed to change your mind about work at any time. (Cool, right?!) 

I’m no stranger to knowing how it feels when your career no longer feels intentional. Every couple of years, I get the urge to shift. I don’t work in either of the fields I majored in. I’ve moved roles and companies. I left the 9-to-5 world to freelance. 

Here are some telltale signs that your career, whether a 9-to-5, self-employment, or something else entirely, feels unintentional (and remember, this doesn’t mean you have to love your job!):

• Your body sends signals. You can’t shake the Sunday Scaries. You’re irritable and can’t resolve it with a solid night’s rest or a hot cup of your favorite caffeinated beverage. (Psst! You don’t have to — and shouldn’t — feel cranky all the time!)

• You feel trapped. You show up because you have to, not because you want to. Every day feels like a slog. Sometimes, it might even feel nearly impossible to get out of bed. And you might even ask yourself, “Is there anything else beyond this?”

• Your values don’t align. You say you value your family, but you work after hours more days than not. You say you value your health, but your doctor flags health concerns at your annual checkup (but you don’t want to admit you haven’t been taking care of yourself because you work too much). Your actions don’t match what you care about most.

• You’ve changed and outgrown your role. Your work is boring. Or it’s given you everything it offers and you crave something new. You climbed the ladder because you knew you should, but now you want to smash the ladder in half. Or you just don’t feel like doing the same thing forever. All normal (and valid) feelings!

What do you do when the signs of unintentionality appear? Burn it all down? Scream into the ether? I don’t have all the answers (sigh), but here’s what I recommend:

• Do the uncomfortable self-work. Pause and reflect. Create space for self-inquiry. What is going well? What’s not working? When do you feel energized versus drained? Consider doing this as a daily or weekly practice so you can pinpoint where you need to make a change. (Sometimes, the results are surprising!) 

• Clarify your work values. We all hold different values, and our values shift over time as our experiences and needs change. What are your work values in this season of life? Flexibility? Financial stability? A pre-defined career plan? A specific title? Once clear, you can consider whether your career supports or conflicts with them.

• Experiment on the edges. Test new interests in low-stakes ways: take an online course, volunteer in a field you’re curious about, or launch a side project. Small experiments can reveal whether a spark of curiosity is worth pursuing further. (This is a better option than burning it all down, no matter how tempting.)

Your career should feel like a choice you make intentionally and not a permanent box you feel stuck inside. Life’s too short to spend 90,000 hours buried in a career that doesn’t suit you best. Change is scary (and hard), but it’s the first step toward something more aligned, more fulfilling, and more you.

Out of Office (Alyssa’s Version)

What I’m doing when I’m not working

• I’m doing the Pure Barre Fall Fit Challenge (30 classes in 60 days) right now, so I am at the barre either first thing in the morning or in the early evening every other day. (Send encouragement, I’m tired, lol). 

• I’m enjoying Artificial Wisdom by Thomas Weaver thanks to @krisandmads and I can’t stop thinking or talking about it. I never thought I’d let AI seep into my reading (for enjoyment) time, but so far, I’m really glad I did.

• Our cherry tomato plant is thriving (I’m proud!), so I’ve been experimenting with new recipes. This Creamy Tomato Gnocchi with Burrata is incredible.

Alyssa Towns is a freelance writer based in Denver, Colorado. She publishes Time Intentional, a weekly newsletter packed with reflections and inspiration about what it means to live intentionally, in honor of her late grandparents, who passed away in their 60s. She uses their losses to remind and teach others that time is finite. She also writes long-form content for brands that are building better workplaces and is passionate about making work a more enjoyable part of life, as we spend so much of it working.