You May Already Be Free
Updated: 1 hour ago
Are the barriers to a more fulfilling life real?
It’s late on a Sunday afternoon and Monday is already pulling your attention away from the family gathering. Maybe you are dreading the nine o’clock staff meeting--another new leader, another AI generated slide deck justifying another reorganization. Maybe you are rationalizing once again why you’re not quite ready to step out of what you dread into what inspires you.
I encounter this form of burnout often. It's actually the part of my work I enjoy most. Let me explain.
This late-career restlessness is common among people from 55 to 62—those who are no longer fulfilled by their current work but are not quite ready for full retirement. The skateboard-riding latchkey kids are now funding 401(k)s, collecting RSUs and navigating another "paradigm shift" or some such thing.
This is what often drives people to seek planning advice from someone like me. However they articulate it in the discovery meeting, the real question is usually some form of “how much longer do I have endure this?”. And in the best meetings they also articulate, “what I really want to do is (teach, volunteer, grandparent, explore, real estate, consult, join a startup, build something, create, etc.).
Whatever the aspiration, they feel it is far away. Executives, doctors or business owners, they all see insurmountable walls and locked doors blocking the way until some countdown clock finally signals their freedom at 65 or 67.
But as we do the work to replace vague notions with real numbers, there can be a Truman Show moment. Remember when Jim Carrey’s character sailed to the horizon and discovered that the “sky” was a painted wall?
This is the moment I love about planning: watching clients discover that they may already be free. The numbers may reveal that the transition toward a more fulfilling and inspiring life can begin immediately.
The walls
Let’s take a look at some of these walls that might have you feeling trapped:
I cannot touch the retirement money until 59½.
I have to make it to 65 for Medicare.
I can’t sell the business for the price I want.
The RSU grants are too lucrative.
These are my peak earning and saving years.
Earning less will damage my Social Security.
Taking Social Security early will reduce the payout.
If I leave this job, I am retiring—and I cannot afford to retire.
No doubt, these are real factors that influence the choices you have. The mistake is assuming there are only two choices. There is the option to keep grinding, maximizing the 401(k), collecting the stock and surrendering Sunday nights until 65. Or there is the option to leap into retirement, stop earning, tap the portfolio and hope you can support your lifestyle.
Option two feels reckless. For many people, it is reckless. So they choose to grind. But there are always more options and if you put the time into it they will be revealed. I know, I see it all the time.
Testing Your Walls
If you are intrigued by the possibility of personal change or feel the tyranny of a retirement countdown clock, you will absolutely benefit from doing the math. I define financial planning as answering these questions: how much money do I need? When do I need it? Where is it going to come from? And what can go wrong?
This is the framework that leads to freedom and false walls crumbling. I will give you a few representative cases I have seen recently.
The clearest case is simply someone that already has enough savings and investments to cover their lifestyle for the remainder of their lives. For example, they live very comfortably on $200,000 a year and have $5 million in dedicated retirement savings. They are ready, they don’t have to wait for Medicare to start or for another $50K in RSUs vesting. You can scale those numbers, a couple comfortable with $100K of lifestyle spending and $2 million in retirement may also be there. It is circumstantial so do the math and see if you are there.
Often, especially for someone in their 50s, they don’t have the resources for full financial independence but certainly enough to pursue something more inspiring. With investment portfolios swollen by extraordinary gains and company stock values well above the most optimistic estimates, some families can potentially fund a bold career change without significant long-term risk. Let’s say that means taking $100K to bridge the launch of a consulting practice. Maybe it means taking small distributions to supplement lower income work, say teaching, but work you will happily do for 20 more years. That math might work.
Or for the business owner? Maybe selling for 10X earnings is an out of reach fantasy, even if your business is fantastic. But training and paying skilled managers, trading less margin for more freedom, might actually work. If you start now, you could be much better off in two years instead of still dreading Monday’s two years from now.
There are too many permutations, tradeoffs, and circumstances specific to your family to know what options will appear, but when you walk through a professionally guided financial planning process that answers the four key questions, they will appear. All of it can be considered, taxes, health care costs, paying off the house, part-time work, sabbaticals, dual income situations, etc. You can touch the walls and find out which ones are real, you can push on the door and see if it is really locked.
The purpose is to put the options next to each other, compare, consider then decide:
Stay in the current role and retire at 65?
Stop working completely at 60 or 62?
Change careers now, earn less and work longer?
Reduce the lifestyle enough to make work optional?
Stay—but stay because you chose it after seeing the alternatives?
After helping hundreds of people prepare for retirement, I know this is not a question to shortcut with a online calculator. That’s like determining how healthy you are with a BMI calculator—useful but woefully inadequate.
The answer may be that you need to stay put for now. It may be that you need two more years, not seven. It may be that the job is already optional.
Thinking of another movie I loved, Ferris Bueller told us 40 years ago “Life moves pretty fast, if you don’t stop and look around once in a while you could miss it.” Your decades of experience confirm the wisdom of that famous line. The time ahead will move even faster than the last 40 years, so take a little time to look around, test the walls, and do the math.
