We’ve all seen the studies or heard the stories. A great boss makes work bearable; a terrible one can send your stress through the roof. Maybe that’s why so many people I know are chasing early retirement.
I’ve had my share of bad managers, especially early in my career. They seemed to be everywhere—sometimes not even my boss, but still ready to ruin my day. Nothing like a surprise gripe right before a client call. Fast forward twenty years, and I’ve ended up with two of the best bosses I’ve ever had.
How much of that change is about them and how much is about me? You can probably guess where I’m going with that.
As you move up the ladder, the boss-worker relationship changes. At entry level you get the menial tasks, often from a junior manager who’s still learning people skills. Sometimes you get lucky and report to someone who’s emotionally smart and supportive. More often, you’re stuck with someone figuring it out as they go.
The best fix? Be your own boss. Bring your own motivation and help others improve. Yes, this is a blog and I’m speaking from personal experience, but I think it applies to many people.
A senior leader once told me to be bold. That stuck with me. Being bold means taking risks, finishing projects, and bringing the team across the line. But how do you act like your own boss when you still have a boss above you? Start by taking care of your plate.
First, respond quickly to emails—especially from your manager. Emails are a stand-in for real conversation. Getting things in writing helps memory and priorities. Leaving your boss waiting for a simple acknowledgment doesn’t help you.
Second, play well with others. Getting along with colleagues and higher-ups matters every bit as much as doing your job. Many companies expect employees to treat coworkers like clients, and 360 feedback—imperfect as it is—matters in reviews.
Finally, anticipate and tackle tasks proactively. Don’t just react.
Master those three things and your bosses will notice. Even the worst micromanager will leave you alone and focus on the people causing problems.
If you think freelancing frees you from bosses, remember you’ll have clients. My wife runs her own chiropractic practice and you’d think she’s her own boss. But difficult patients can drain her just as badly as a bad manager. Whether you’re a consultant, author, or plumber, you still deal with people—and people can be unpredictable.
Careers aren’t easy. In your 20s you’re adjusting to a new reality—far different from part-time jobs or internships. For the next 20–40 years you’ll likely spend weekdays working long hours. That’s a shock after college freedom, when you had more control over classes, naps, and your schedule. So no wonder many 20-somethings focus on happy hours.
By your 30s, with family and bills, you’re still getting used to “the career thing.” Your 40s are pivotal: debts should be falling, your work reps add up, and life becomes easier if you’ve managed things well. If you stress easily, you might start looking for exit ramps.
I can’t speak for your 50s and 60s, but my friend Fritz from The Retirement Manifesto prepared well and retired at 55. He’s living a life many of us dream about—few regrets and lots of hiking and cold-water swims. He probably could’ve worked another decade or two, but he chose different plans that don’t need a 50-hour Monday–Friday commitment.
Bottom line: learn team dynamics and pick up cues from successful coworkers and your career will smooth out over time. It’s ironic that many who retire early in their 40s or 50s leave precisely when they’ve mastered their careers.
On the home front, partnership matters. Problems arise when someone feels dominated at work and at home. Be a servant leader at home: show empathy and share the chores—watching kids, vacuuming, washing dishes. Don’t fake joy about scrubbing floors, but do what you can to avoid resentment, which erodes relationships.
Try getting up early to carve out time for yourself. I’m up at 5:15 most mornings and use that hour and a half to write this blog. Writing is therapy for me, and sometimes the page views stroke my fragile ego.
Don’t worry—I’m still focused on building a war chest (aka “F-you money”) so I have options if work gets messy. July 2019 is coming up fast. I’m enjoying my weekends and the chase at work. A decent job has hidden perks: daily interactions, colleagues to commiserate with, and routines I like—especially when I can cycle to work in the warmer months. Having a place to go Monday through Friday suits me.
Sometime in the next year or two—or maybe three—I’ll need to figure out how to replace the routine, relationships, and refuge. I’ll be watching early retirees for ideas. In the meantime, be bold. Realize that half of what makes a boss bad is often a reflection of your own performance. Take that to heart and the journey will get a lot easier.