Should You Stay or Quit? How to Know When to Bet on Yourself

Am I a hypocrite for saying this? You decide.

For years, I’ve been selling the dream of getting promoted and better paid.

But here’s the bitter truth—

Traditional career growth is a mirage for most people.

The odds are stacked against employees, especially women and minorities. Macroeconomics, mismanagement, layoffs, discrimination—forces beyond your control determine your fate.

So why bother?

Why fight for a promotion?

Why push for a pay raise when you’re already exhausted?

Honestly, you don’t have to.

Because the real value isn’t in a new title on LinkedIn. It isn’t in an extra $481.65 on your paycheck...

The real value is in unlearning the myths we were taught to believe:

• Work hard.

• Stay humble.

• Respect institutions.

• Don’t bet on yourself.

I’ve worked with clients who followed these rules for decades—only to realize they were running on a treadmill, not climbing a ladder.

Once they see the truth, they do three things:

• Stop waiting for permission.

• Step into authority.

• Start betting on themselves.

For some, betting on themselves means finally asking for the promotion they want and getting it.

For others, betting on themselves means stepping off the treadmill altogether.

Like Kayla—getting let go from a toxic job was the push she needed. Within months, she made her first $10,000 running her own coaching practice instead of working for a micromanager with anger issues.

Or Saho—an experienced media trainer finally preparing to leave an agency that treats her like a commodity, not the one-of-a-kind devoted expert that her clients love.

Betting on yourself is risky—but so is staying stuck.

I know because I’ve been there.

When I left my tech job in 2016, I didn’t have a perfect plan. But I knew I wanted more than what traditional career paths offered me.

After getting the promotion I advocated for, I no longer wanted to climb higher within the system.

I’d seen enough. I’d keep getting sick from the chronic stress of staying where I didn’t truly belong.

I wanted to build something of my own—a path that was as unique and humane as my consciousness.

For years, I worked a part-time job to pay rent while I hustled to build a scrappy coaching and speaking business.

(While we're being honest, let me admit that it totally helps that I live with my life partner, someone who kept a well-paying tech job and health benefits.)

Steadily, my work and life became richer.

For the past five years, I’ve consistently out-earned my old salary—partly because I’m privileged to work with privileged people.

And I work hard to keep my coaching practice aligned with my values of mastery and integrity.

But beyond the money?

I no longer get sick like I used to. I no longer lash out at my partner, having bottled up the rage of a thousand paper cuts at work.

I’m healthier. More creative. More at ease in my own skin.

None of this is easy.

Working for yourself is NOT the answer for everyone.

And the goal isn’t instant riches.

It's something more sacred—a connection to your own god-given creativity and your ability to generate value in the world.

To cultivate self-respect that runs deeper than any socialized fear.

So...

I'm super curious --

Is working for yourself, whether as a side hustle or as your main gig, something you're also thinking about?

Or maybe you already do.

Either case, I'd love to know how you most want to bet on yourself.

Send me an email at jamie@jamieleecoach.com or leave a comment on this blog post.

From one risk-taker to another,

Jamie