Stop Preparing to Change Careers and Actually Change Careers

Question: I’m 36 and have spent 11 years in payroll. I hate admitting this, but I’m bored enough to cry during spreadsheet cleanup. I want to move into project management, but every job posting wants experience I don’t have. I’ve rewritten my resume six times and taken two online courses. What am I missing?

You’re missing evidence, not another course. Payroll already contains project-management work: coordinating deadlines, fixing broken processes, communicating with people who are stressed, and preventing expensive mistakes. You’ve probably been doing the job in disguise.

Make a list of three projects you’ve handled. For each one, write the problem, your actions, the people involved, the deadline, and the result. “Processed payroll” is a task. “Coordinated a payroll-system transition for 200 employees with zero missed paydays” is project-management evidence. Put those examples in your resume and use them in interviews.

Also, apply before you feel ready. If you meet roughly 60 percent of the requirements, send the application. Job descriptions are wish lists written by people who would also like a pony.

Question: I quit my marketing job six months ago because I was burned out, then spent the first three months “figuring things out” and the next three months avoiding LinkedIn like it owed me money. Now I’m embarrassed about the gap. What do I say?

Tell the truth without writing a memoir. “I took time away to reassess my direction and am now focused on roles in nonprofit communications” is enough. Then prove the second half. Volunteer for one real project, freelance for one small client, or create a portfolio piece that shows current skills.

And yeah, the avoidance is on you. Not because you’re lazy, but because hiding has become more comfortable than being judged. Comfort is expensive when you’re job hunting.

Question: I want to start a bookkeeping business, but I keep tweaking the name, logo, website colors, and Instagram bio. My friends say I’m procrastinating. Are they right?

They are right, and annoyingly, they may be saving you from yourself. A logo cannot tell you whether anyone will pay you. Before touching the branding again, contact 10 people who might need bookkeeping help. Ask what they currently do, what frustrates them, and what they pay. Offer a small, clearly priced service to the first three.

Today, create a one-page document with three project examples from your current or past work—or, if you’re starting a business, a one-sentence offer—and send it to one real person before dinner.