Planning Your Career Around Your Life (Before It Plans Life for You)

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Plan Your Career Around Your Life (Before It Plans Life For You)

The old adage: to fail to plan is to plan to fail—it’s true in careers, too.

Careers are tricky. Too many people chase the next paycheck or promotion without asking the most important questions:

Where do I want my life to be? What do I want it to be?

This post is for folks early in their careers. If you just need a job, there’s still value here—but I’m talking to people who want a path that aligns with their skills, values, and long-term goals.

Before you polish a résumé or sprint after job postings, stop and ask:

• Where am I willing to work, and what am I really working for?

  
  

If you don’t answer that honestly, you’ll spend months in a scattershot hunt—landing roles that fill a bank account but drain the soul.

Here’s the truth: if you don’t plan your career around your life, your career will plan your life for you. And usually not in a way that leaves you happy.

That’s how the golden handcuffs get locked on. Once life reaches the point where you must have this job and must have that income (diapers are expensive), leaving gets tough.

You can wake up bitter, stuck, and wondering how you got there.

Start With Life, Not Work

When I coach, where we start depends on stage and need. But the basics don’t change:

Location, mission, lifestyle. If you’re not willing to move, say so. If you want to be close to family, own it. If the mission matters more than money, (or the other way around) be clear.

Career vs. paycheck. If all you want is a paycheck, fine—just don’t pretend it’s a planned path.

I want to stop for just a second. Yes, many a person has just taken a job with a company, that turned into a career. If that happens be grateful. But over the last four decades even those people that ended up there, have said to me, "this is not where I thought I would be."

Be deliberate: Does this job move me closer to where I want to be in five years?

Trade-offs. You can’t have it all—salary, mission, location, growth—at the same time.

Rank them. Decide what you’ll flex on and what’s non-negotiable right now.

Priorities shift. Maybe you’ll put growth above all else early on willing to move every two years and chase the next big challenge.

Later, location or stability might climb to the top.

Maybe you’re willing to pay $3,600/month in Silicon Valley and live on ramen for two years because the experience will set you up to start your own business back home later.

That’s a choice—make it consciously.

Manage the Career You Start

Oh, you thought it was “get it started and it’ll all work out?”

Nope. You’re usually one corporate buyout away from starting over.

(Yes, I have been there.)

This is where being deliberate about your plan and vigilant about the market intersect.

If the market is demanding skill X now, and your job keeps you locked on skill Y with no path to cross over, you need to re-evaluate.

• COBOL programmers were once the backbone of banking and government systems—now it’s a niche. Some still do well, but most watched demand fall as newer languages took over.

  
  

• Flash developers were red-hot in the 2000s—then support died and mastery of an “essential” skill became useless almost overnight.

  
  

Point: staying still is sliding backward. Keep your skills moving where the market is headed, not just where you’re comfortable.

Be honest about how much time you’ll give any employer to get where you truly want to be.

Be just as honest about when it’s time to move on.

Priorities will change—plan for it.

The Five-Year Bites

A mentee told me, “Sir, I have no idea where to start.”

I said: “Write your life in five-year bites—and no work/career talk.” 

Make simple qualifier statements. Let the life you want to live shine a light on the career you need to plan.

At 25 I want…

At 30 I want…

At 35 I want…

At 40 I want…

He came back with:

• 25: travel and see some of the world

• 30: know where I want to live

• 35: married with kids, own a home

  etc.

No career talk. Just life.

Then we worked backward: Where will that family live? What kind of place? What kind of stability?

If you want that at 35, maybe you grind it out in a one-bedroom in a city you don’t love at 25—traveling, figuring out where feels like home, and building the skills that get you where you want to be at 30.

That’s planning:

Tie career steps to being the vehicle for life steps. 

We worked this for a few months. He’d bring ideas; I’d ask, “Did you think about this?”

I made it clear: Plans aren’t etched in stone. Life changes. You might plan to be somewhere for a few years and—boom—love shows up.

That doesn’t derail everything; it means you step back, run the process again, and re-evaluate.

Trade-Offs Are Real (Again)

You can’t have salary, mission, location, and growth all at once.

Rank them. Decide what’s non-negotiable and what you’ll flex on—and for how long.

Maybe you take less pay for mission now, then shift later for family stability.

That’s okay. Know it. Plan it. Move intentionally.

The Lesson

That intern? He took a stretch role in Columbus he wasn’t thrilled about after he graduated. Learned a lot over the next few years.

Then Detroit for two years—more growth, plus classes to fill skill gaps that became obvious in the work.

Then he landed the job outside Chicago—right where he wanted to be, just past 30.

Bought a townhouse. Got promoted a couple of times. Met a schoolteacher at dance class. Married at 33 (ahead of plan—because love).

When kid #3 was on the way, they sold the townhouse and bought in the suburbs.

Today: three kids, director-level career.

He still reaches out sometimes to say thanks—and admits he plagiarizes my stuff in his own mentoring program.

Not because I told him which job to take. We talked about almost everything except jobs.

He learned to plan his career to support the life he wanted to live.

“We talked recently; now they’re in the thick of post-career planning.”

After all, once your career is done, life is still there—and it won’t wait for you.

If you’re early in your career, don’t just grab what’s easy.

Think five years ahead. Write it down. Map it.

Make the job serve your life, not the other way around.

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