How to Leave a Career You Don’t Genuinely Love

Elevator door with glowing orange interior. How to leave a career you don't genuinely love. Common advice from life coaches and career gurus is to build a career you love so much you don’t want to retire. 

I appreciate this advice and wish I’d followed it more in my 20s and early 30s.

But genuinely loving what you do is a rare privilege. Most people don’t love their jobs, let alone their careers. 

Early on, we might like our jobs or tolerate them enough to use the income to qualify for a 30-year mortgage and get comfortable in a certain lifestyle.

But then we’re trapped because we need the same income level or more to service the debt and maintain the way of life. Lifestyle inflation kicks in — income grows; spending follows.

It’s gradual confinement

The day may come when we wake up and realize our situation feels inescapable.

We have three choices of action. 

  • Live with it
  • Make a change
  • Have a mid-life crisis

I was on this path two decades ago. I chose a lucrative career in my 20s with limited job satisfaction. The only joy came every other Friday

Claustrophobia kicked in a few days after I bought my first home in September 2006. Marriage and kids followed. 

Were it not for my pursuit of early retirement, I might be amid a mid-life crisis. But I took action years ago to build a financial buffer between what I earned and spent, investing for our future.

The plan execution was far from perfect I’m still not exactly where I want to be. But I’ve come a long way.

This article isn’t meant to criticize our choices or situations many of us find ourselves in. Steady careers give us good health care and pay for necessities and embellishments. That’s a privilege to be grateful for.

But we can mitigate career discontent.

Is this Love? The $10 Million Test 

Is this love that I’m feeling?
Is this the love that I’ve been searching for?
Is this love, or am I dreaming?
This must be love
‘Cause it’s really got a hold on me
A hold on me

— Whitesnake

Here’s a simple thought experiment to determine if the love for your career is power-ballad-worthy.

If you were given $10 million today, tax-free, would you still be working the same job in the same career one year from now?

I suspect nearly all of us would not continue spending our professional time the same way every day. Most in a full-time job would quit. Many self-employed or business owners would modify their work.

Maybe not immediately, but soon. 

Why $10 million? 

  • $1 million is not enough these days. Not in an urban area with a family and kids going to college. 
  • $5 million is probably enough for most people. Even Suze Orman thinks that’s the minimum. 
  • But $10 million is a definitive “yes, that’s enough” for nearly everyone. 

Congratulations if you would continue working the same hours in the same career after receiving the $10 million.

You are a rare breed, and I admire you and your career choice. 

For the rest of us, keep reading.

How to Leave a Career You Don’t Genuinely Love

Before we move on, I recognize there’s a complex spectrum between hating your job and loving it. Career satisfaction fluctuates. 

I’m grateful that my former career allowed me to save and support my family. We don’t need to love our work for a meaningful, lucrative, and productive career. 

This post is for people who have a strong desire to leave their careers.

Early in our careers, we find ourselves in a decent-paying job with benefits, friendly coworkers, and a visible career path. The future looks bright!

But years later, you might hit a point where you ask yourself, what am I doing with my life? 

If you genuinely want to change your life and escape a career you don’t enjoy, there are escape routes but no shortcuts.

One way is to save and invest your way out. Financial independence gives us options to modify our lifestyles. 

There are also opportunities to create new ways to earn a living. 

I enabled my career change by combining investing and a side hustle.

There are other ways to accelerate the transition toward financial independence, retirement, or a more meaningful professional life. Here are some ideas. 

Excel at Your Job

Even if you don’t like it, you’ve built a career that allows you to earn a living. Reliable and high-performing employees eventually rise, receive promotions, and make more.

Exemplary employee can leverage their reputation to earn more and find better opportunities at the current company or the next. 

Don’t squander the extra earnings. Save and invest to reach financial independence sooner. 

Control Living Expenses

It’s elementary but still so hard to do. Inflation doesn’t help. 

Maintaining your current living expenses means being content with your current lifestyle and relentlessly resisting the temptation to increase spending when there’s more money available.

Controlling living expenses is a superpower enabling the pursuit of alternative careers. 

Build Supplemental Investment Income Streams

Use excess cash flow from your day job to create passive investment income streams.

Over the past two decades, I built a stock portfolio large enough to produce a significant monthly dividend income stream. We’re living off dividends as I transition to self-employment

Real estate rentals are even better. I sold my rental property in 2019, but it was a solid income stream for many years.

Crowdfunding allows us to create passive real estate income with smaller investment amounts and reduced risk exposure. 

Start a Side Passion Business

The Internet has empowered millions of entrepreneurs. Starting an e-commerce business or becoming a content creator online is straightforward. 

Better yet, startup costs are very low — online businesses are low-risk endeavors. 

When you start a business about something you’re passionate about, you can create a career you love and never want to retire from. 

I started my blog in 2013, and it’s led to opportunities I could have never imagined. Now it’s supporting my family.

The hardest step is the first one. 

Reach “Enough”

Retirement is a feasible route to escape a career you don’t enjoy. But that takes decades. 

If you’re already a few decades into it, now it’s only a matter of determining how much money is enough

I’ve written about the financial independence number. Target an investment portfolio that equals 25 times your annual spending.

That’s a rule of thumb.

For a more definitive answer, experiment with an online retirement calculator such as NewRetirement for a detailed visualization of your wealth. 

Practice Career Agility

A more agile career is an effective way to earn more money, keep things fresh, and test roles ideal for your skill set.

Trying different companies and positions over your career could lead to better fulfillment — maybe even enough to pass the $10 Million Test

I stayed with a mediocre employer for 14 years. Had I changed employers a few more times, I may have found a better career fit and more job satisfaction. 

Instead, I became complacent in an easy role and was wrongfully intimidated by an overbearing non-compete. 

Job hopping may lead to a healthier and more lucrative career. 

Love the One You’re With

And if you can’t be with the one you love, honey. Love the one you’re with — Stephen Stills

The most practical solution to this problem is to develop a sincere and genuine love for the career you’ve already built. 

This is 100% possible. I worked with many people over the years who really did love what they do, even though it wasn’t for me. 

Beyond the $10 million threshold? Maybe not that much love. 

But there is always room to embrace the relationships, team successes, and collective accomplishments in corporate environments. Big companies and teams achieve extraordinary things.

Passionate people designed the first iPhone, animated Disney’s Moana, discovered insulin, and figured out how to cut hair evenly with a vacuum. They extract millions of barrels of oil from the Gulf of Mexico, create new vaccines, record inspiring music, and push the limits of what’s possible. 

Contribute to the achievements. Encourage excellence with your valued team members. Celebrate success with Safeway cupcakes at the monthly status meeting.

It’s healthier than carrying the burden of hating your career.

Photo via DepositPhotos used under license. 

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