Chad Willardson, President & Founder of Pacific Capital and Platinum Elevated. Best-Selling Author of Wealth Wired Differently.
Tell me who hasn’t daydreamed about the day you hand in your work badge and office key, shut down your computer and just ride off into the sunset—bank accounts full, still young and finally “retired”? It sounds like the ideal setup. But I believe this romanticized vision of retirement is old school and not relevant to everyone today.
In my nearly two decades of experience as a wealth manager, I’ve worked with hundreds of retirees. I’ve provided guidance on how to retire early and wealthy, what to know about retiring in expensive areas and having a resilient retirement plan. Through this experience, I’ve seen that rather than dreaming of an escape from work before 50, many leaders today focus on financial independence and meaningful activities that spark purpose and passion.
Here’s why I believe the traditional concept of retirement has changed and how entrepreneurs and executives can work on building true freedom instead.
Life expectancies are longer, and the nature of work is evolving.
Back in the day, the idea of retirement made a lot of sense. Many jobs were physically exhausting, and people didn’t live as long. Fast-forward to the 21st century, and lifespans are increasing, healthcare has advanced and more jobs rely on mental endurance, rather than raw physical labor. One of my key employees works remotely from Bali and surfs every single day. For a lot of jobs these days, you really can work from anywhere.
Retiring from work isn’t always the carefree experience some might imagine. Boredom and lack of purpose are common when the daily routine disappears. Many older adults who retire experience cognitive decline after leaving work. Put simply, that sudden change from being fully productive to having little to zero activity can make you feel very unanchored.
In my view, the old ideal doesn’t mesh well with modern longevity. Instead, I encourage entrepreneurs to think of retirement less as a finish line and more as a pivot point. Look at it as an opportunity to work on what fascinates you rather than running away from responsibilities altogether.
Escaping work isn’t always the goal.
You know how you often hear the phrase, “If you love what you do, you’ll never work a day in your life”? At the end of the day, even if you love your job, it’s still work. But having work that interests you and gives you a sense of purpose is often what helps keep people fulfilled.
Warren Buffett, who recently announced his retirement after 60 years of leading Berkshire Hathaway, stayed with the company for so long because he said he enjoyed the work. He likely could’ve kicked back decades ago, but he stuck with it because he liked what he did.
This mindset isn’t just for the rich. Many who retire early find themselves looking for something to fill their time. Surprisingly, having “nothing to do” can get old pretty fast. I see it a lot with entrepreneurs, executives and creatives who’ve built careers around what they’re passionate about; they often don’t feel the need to stop completely because they find their work fulfilling.
Traditional savings don’t work for everyone.
If you’ve come across the “financial independence, retire early,” or FIRE, trend online, you know there are some interesting strategies, like really going hard on saving and investing and spending as little as possible. While this can work for some retirees, here’s a little reality check: Many people who leave their jobs return to working after a few years, especially if they retired early in their careers. It’s unexpected, but life doesn’t stop when you decide to retire. There are a number of reasons retirees choose to rejoin the workforce, a big one being money. Rising healthcare costs, unpredictable markets and inflation can slowly eat away at an entrepreneur’s savings.
The idea of having just one big retirement fund might not be enough to cover 30 or more years of living, especially if you retire young. It’s not that saving isn’t important—it absolutely is. But instead of just aiming for that one perfect amount to last forever, entrepreneurs can consider having different ways to bring in money. Things like real estate, dividends from investments, a business on the side, freelance work or consulting can offer flexibility and help make you more resilient.
How Leaders Can Find Freedom
Retirement shouldn’t be about just stopping everything cold turkey. It should be more about having the freedom to decide what you want to do with your time, your energy and your skills. Real independence means you can slow down or totally switch gears whenever you feel like it, without stressing about paying the bills in the coming months. It means you can finally dive into those passion projects you’ve always thought about, spend time helping out younger folks in their careers or even try out a whole new career if something catches your eye.
I believe that when you set up your finances wisely—such as through investments that grow over time, businesses that can run without you being there all the time or side projects you can dial up or down as needed—that’s when you really gain true freedom. You’re not being forced to quit; you’re just in a position to call the shots and change things up as your entrepreneurial and personal goals evolve.
Ultimately, the narrative of traditional retirement isn’t always the right fit for everyone today, especially if you’re still under 50. Instead of counting down the days until you can stop working, I think the goal should be to change your work into something that makes you happy. Because, honestly, retirement is more about having the freedom to live life exactly how you want, with your time being the most valuable asset.
The information provided here is not investment, tax or financial advice. You should consult with a licensed professional for advice concerning your specific situation.
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