Financial Freedom: How to Know When to Pursue Your Dreams

Jul 30, 2021 | Executive Coaching, Financial Fitness

This talk about The Great Resignation may have you thinking it’s time to jump ship.

During an extended vacation in Alaska in July, I, too, found myself wondering how long before I could retire and be on permanent vacation.

While I’m completely satisfied with my current career choice, I share my thoughts, just in case you’re wondering the same.

Could you turn in your resignation tomorrow, consider yourself a success, and continue to live a lifestyle that makes you comfortable?


Financial Health Impacts Career Decisions

The Covid pandemic has changed the way some people view work. Individuals are pushing back on the pressure to perform under conditions that threaten their physical or mental health. See Simone Biles’ famous withdrawal from Olympic competition as a prime example.

After so much uncertainty surrounding the workplace, people are struggling in their journey of “what’s next?” Regardless of age, there’s a considerable number of executives who are asking Mid-Life Crisis questions: “What’s my purpose? And have I been living it out?”

Millionaires have delayed self-gratification and worked hard to build legacy wealth. They’ve put off vacations and made personal sacrifices. And they’re asking, “For what?”

As the pendulum swings, people are now seeking more psychological safety and establishing personal boundaries to protect their own physical health. We are prepared to jump ship rather than accept undesirable terms that appear to threaten our physical, emotional or spiritual security.

Executive Coaches don’t pretend to be financial planners, personal trainers, ministers, nor psychologists, but there’s an element to coaching that requires understanding the whole picture.

Sometimes, when you feel financial pressure, it impacts how you think through career decisions. You feel pressured to pursue a promotion.   Pressured to stay in a job that isn’t a good fit because you make great money, or you need the health insurance benefits.

If you find yourself at a career crossroads, take a holistic approach that first establishes healthy practices in all areas of your life. Allow yourself time to find a better balance – physically, mentally, spiritually, financially –before jumping into a new circumstance. Your career and life decisions stand a much better chance of serving you well after doing some self-work.

For instance, you may discover that your relationship with money has not been a healthy one.


What Financial Independence Is Not

I have known high-income wage earners who defined financial independence as being able to go months without reconciling their bank statements. They don’t notice until there’s no money left in the checking account, and they find themselves as needy as someone who doesn’t have two pennies to rub together.

“I don’t make enough money,” they’ll say. “I need a bigger salary. I need to get promoted.”

“Why do you use the word ‘need?’  Help me understand why you need this this massive promotion.”

“Well, I’ve got a lot of expenses. I’ve got kids in college, and I’m leasing a Bugatti. I’ve got three homes with mortgages, and this stuff doesn’t come cheap.”

If your idea of the American dream is just “make more to spend more,” you are never going to get ahead. Long-term financial independence demands intentionality in budgeting and disciplined stewardship, rather than blindly burning through cash.


How to Know You’re Ready

Individuals’ working definitions of financial security vary.

There’s a series of questions that we ask on the inclineHR personal baseline assessment that explores the mindset surrounding finances.

There seems to be two camps when it comes to money management.  Those who spend prodigally and those who save frugally.  It’s those who have saved all their lives, when they do the calculations, discover they’ve amassed a couple of million dollars and realize it’s time to enjoy life a little more.

Are you ready to walk out that door on your terms? Consider these questions.


  • Do you know your net worth?
    Sometimes you think you’re better off than you really are. Calculating your personal net worth allows you to “stand in your truth” and make informed decisions.
  • Do you know your monthly operating budget?
    This should be a simple calculation of all basic necessities, plus your monthly debt burden for mortgages, car payments, credit card bills, and other personal loans. As mentioned above, inattention to this detail sometimes brings disastrous results through reckless spending.
  • Do you have cash reserves?
    If you were to be downsized, the total amount of your liquid assets should be enough to cover your monthly operating needs for the time it takes to replace that lost salary. Optimally, keep an emergency fund that equals 8 months of your current living expenses.
  • What are your lifestyle goals?
    If your priority is to continue the current work-from-home arrangement so that you have more time with the family, be prepared to settle for less cash if the compromise agreement is a job share with another co-worker. In the past, employees have traded time for money. Now, they sacrifice money for the more-valued commodity, time.


If you have no debt and can maintain the lifestyle you’ve created without touching your savings, your career options become wide open.  I’ve counseled folks who realize $5000 a month is enough to keep them comfortable. That equates to $60,000 a year, after taxes – so, calculate a $100,000 annual salary.

That may be a sizeable drop from your current income. But, knowing that you will survive frees you from the fear keeping you in an untenable job because the money is “too good.” That’s financial freedom.


“Freedom’s just another word for nothin’ left to lose.”  

Kristofferson, Kris and Fred Foster. “Me and Bobby McGee” (1969)


Living in Freedom

If you take this lyric and reframe it in the context of “regardless of the choice I make today, I cannot lose,” I believe you now have a working definition of financial freedom. Freedom to do with your time and talents whatever feeds your energy and fulfills your purpose.

Should you decide to take part in The Great Resignation, you are able to take on work that is more meaningful for you when you have achieved financial independence. Winning could be defined as career advancement, retirement, or semi-retirement with time for volunteer work in causes you deeply support.

If you choose to step back from fulltime work, extrinsically, you won’t see as big a return as the salary you once earned. Intrinsically – if you can still afford to meet your basic needs – you could find yourself operating in the Self-Actualization range on Maslow’s Scale.


At inclineHR, we have four legs on our coaching stool: physical health, mental health, spiritual health, and financial health. We believe a gap in one or more of those areas tends to show up in leadership decisions and career choices.

If you are contemplating a career move that’s motivated by a need for more income or more flexibility, our coaches are ready to guide you through the evaluation and preparation process to make your best move.

Contact inclineHR. We build exceptional leaders.