Stop Waiting for Permission: Career Lessons From My 20s

Welcome to the fifth and final edition of Jobtober! The little tiny pumpkins are taking over your grocery store window display, and for many of us…it’s OPEN ENROLLMENT season! In this five-part series, we’ve explored how to make your job work for you and how to improve your life at work (well, at least the financial part of it). We’ve already covered employee benefits, layoffs, consulting, and negotiating, so let’s look at everything I regret about my career. Yikes!

Key Takeaways:

1. Most of what you try won’t work, but staying in motion creates the conditions for luck to find you.

2. Saving early, negotiating every role, and understanding benefits shape your long-term freedom.

3. Saying yes to everything can open doors, but knowing when to stop is what keeps you sane and solvent.

In my mid-twenties, I felt stuck in my career. I was five years into book publishing, working in the academic division. The job was a volume business: chasing down tenured professors to turn their dissertations into monographs, packaging up research that maybe fifty other people in the world would ever read. At first, I loved it. There was a thrill in convincing a scholar to sign with me, in helping ideas make their way into print. But over time, the shine wore off. I was doing the same work on repeat with almost no increase in pay. The projects that actually excited me—the kind of books that felt alive and urgent—I was told I could work on them, but only in addition to my regular output. That kind of hustle didn’t come with more money, and at the rate they were paying, I couldn’t even afford to live a reasonable distance from my office.

At the same time, I was desperate to break into food writing. I went to networking events, sat through conferences, collected business cards, and cold-emailed writers I admired (almost no one replied). Late at night, after long days of academic publishing, I was testing recipes, writing essays for tiny checks, and trying to wedge my way into a world where I had no connections. I hadn’t gone to the right schools. I didn’t know the right people. Every path in felt blocked.

What changed wasn’t my résumé or my network. It was momentum—the sheer fact that I kept showing up, even when it felt pointless. Then one night, scrolling Facebook, I saw an author of mine post a job opening at a music media company. The job sounded like it had been written for me. I threw together a short cover letter and my publishing résumé, expecting nothing. I had no “in.” Which is why I nearly fell out of my chair when the hiring manager emailed me back. Somehow, he looked at my academic publishing background, my freelance food writing, and the odds and ends I’d been piecing together, and he saw what I saw: that I was actually perfect for the role.

That job changed my life. I met some of my closest friends there. I met my husband there. And most importantly, I finally got to work on the kinds of projects I’d been chasing after in the margins of my day job. Looking back, it didn’t feel like a straight line. Most of my efforts—late nights writing for very little money, conferences where no one remembered my name—went nowhere. But they kept me in motion, and once I was moving, luck had something to work with. Just so we’re clear, what I mean by very little money is being paid $100 for an essay or recipe that took at least six hours to research, interview, transcribe, write, and edit.

Looking back, what felt like luck was really just years of trying different things, most of which went nowhere. I’d gone to the events and done the side hustles. None of these efforts paid off directly in the moment, but all that work did keep me in motion. And once I was moving, luck had something to work with.

It’s funny when you read autobiographies of twentieth-century entrepreneurs, which are mostly about white men over fifty. They always skip lightly over a particular part of their story: how they got their first job. There’s usually a dad, a coach, or a family friend who gave them that first job. I don’t begrudge them their success, but it always makes me laugh when they frame their careers as pure grit and genius while ignoring the enormous leg up they got from inherited connections or a family loan. I’ve had plenty of privilege in my life, which I acknowledge openly, but I didn’t have those kinds of shortcuts when it came to my career. I might have if I’d gone into the same career as my parents, but I chose a different path. One where I didn’t have any prior connections. However, what I did have was the willingness to keep trying new shit, even when most of it wasn’t working.

And yet, even with that persistence, there are still some career moves that I wish I’d made earlier. Some I learned the hard way, others I’ve borrowed from smarter people. If I could go back in time to the start of my career, here’s what I’d tell myself/

I wish I’d treated my career more like a business. For too long, I acted like an employee waiting to be noticed instead of someone responsible for managing her own professional assets. A simple contact log would have made a huge difference—nothing fancy, just a spreadsheet to keep track of names, emails, conversations, and follow-ups. Relationships fade if you don’t tend to them, and neglected relationships are missed opportunities that often have financial consequences. And remember, if you do get laid off, you might lose access to all your contacts! So save those important email addresses somewhere while you can. (Well, maybe first read your company policy on that so you don’t get sued.)

I wish I had been better about contacting people I admired. When I did send those “I love you, can I pick your brain” emails, they were vague and forgettable, and I shouldn’t have been surprised when most went unanswered. Now that I’m on the receiving end of some of those emails, I see exactly why. A stronger email doesn’t just say, “I’d love to ask you some questions.” It’s direct, respectful, and specific: “I admire your work. I’m trying to break into [field], and I’d love to hear about your experience at [company]. Here are three questions I’d be so grateful for your perspective on.” Even if it’s just a short email reply, that’s much easier for someone to respond to. And for the love of god, always say thank you. Gratitude makes people remember you.

I wish I’d started keeping a record of my achievements: promotions, raises, freelance pitches. When the time comes to craft an ask for one of these things, it’s so much easier if you already have concrete examples at your fingertips to use as templates. And that means ALWAYS having an updated résumé or website with all of your stuff on it.

I wish I’d learned to read a benefits package earlier. At the time, I cared only about salary. I didn’t understand that retirement contributions, healthcare costs, and stock options could add up to tens of thousands of dollars over a decade. A job that looks “lower paying” on paper can actually be the better financial decision if the benefits are structured well.

I wish I’d been a better saver earlier on. Even a modest cushion changes how you negotiate, how you leave jobs, and how you handle risk. Without savings, you constantly have to play defense and are stressed about running out of money. I was always stressed about money. Honestly, it wasn’t until I got married that I felt the terrible weight of fear of running out of money lift. With savings, you get to play offense. That’s a financial truth that extends beyond just your career—having money in the bank is about power and freedom.

I wish I’d been more strategic about free work. Early on, I said yes to underpaid and unpaid opportunities because I wanted experience, and sometimes that was the right call. In fact, early on in your career, it’s almost always the right call. Writing for exposure occasionally opened doors for me. But the problem was, I stayed in that phase too long. The hard part isn’t working for free; it’s recognizing when you’ve outgrown it. If you don’t draw the line at some point, people will happily let you work for free forever. The transition from “yes to everything” to “my time costs money” is awkward, but financially and professionally, making this switch is essential. I didn’t make it soon enough, and I’m still struggling with some of the setbacks that caused me. I think saying yes to everything that MIGHT help me has led to a lot of my success. But it’s also led to a lot of unnecessary and unnatural stress. And very early mornings (she says as she edits this at 5:49 am). Sometimes you have to say no, and I think the most successful people are the ones who nail this transition.

I wish I’d negotiated my pay at every job. Even small bumps in pay compound over time, especially once retirement contributions are tied to them. I thought negotiating was about getting a bigger paycheck right away. What I didn’t realize was that every missed negotiation set the baseline for my future raises and cost me far more in the long run.

I think the best advice I can give is that it’s benefited me greatly to always be working on the next thing, to always have not just a job, but something else career-related that gives me energy. I wrote freelance articles about food while I was working as a book editor. I started my financial planning business while I was writing album reviews for a music website. Maybe that makes me a crazy person, but I have found success in what I’ve done, not just by hard work, but by saying yes to as many opportunities as possible. You never know which side thing will turn into your next chapter, but having one keeps you less dependent on a single paycheck.

If I could tell my younger self one last thing, it wouldn’t be about résumés or networking events. It would be this: stop waiting for someone to hand you your next step. Apply anyway. Pitch anyway. Save anyway. Just do something. Most of the seeds you plant won’t sprout, but a few will. You really only need one to change everything.

Parting shot: Remember, one “yes” can pay for a decade of “no’s.”