“What’s an opportunity or pursuit that you passed on earlier in life, but if the opportunity came again, you would consider taking it?” 

This is a question I contemplated a lot during our last three-month road trip. And this year, while I’m working a max of 8 hours a week, I’m still considering. 

The Roads Not Taken

Our lives are full of roads not taken. Paths diverged, and we made a choice. One choice pulled us farther away from the other choice. Maybe you have regrets. But most likely, you don’t. The choices we made brought us to where we are now. 

The mistake is thinking that once the paths diverged, they will never loop around again. There were lots of good reasons you didn’t choose that other path at the time. 

But what if you had another chance? Would you still be interested? Is there still a spark of curiosity or excitement? 

For those who are being intentional with their money, paying down debt, saving, and investing, you might have more agency than you think. The path might not circle back on its own, but you can make a detour and find it again. 

Mini-Retirements and 2nd Chapters

I talk with my coaching clients a lot about their 2nd chapter. The first chapter is the part of your career where you are paying down debt, getting established, and saving for retirement. A big focus in the 1st chapter is often optimizing income. 

For some people, the 1st chapter never ends. But for those on the financial independence journey, you start thinking about the 2nd chapter at some point. The second chapter probably involves some type of work, but you might not be optimizing for income anymore. Instead, you might start optimizing for time with family, health, purpose in your work, work-life balance, and more interesting or challenging work projects. 

There is this false narrative in the American culture that it’s okay to switch careers in the 2nd chapter…..BUT it better be seamless. Two weeks tops between careers. The expectation is that while you are burned out and overwhelmed in your current career that has consumed your life for the last 15+ years, you can also rest, recuperate and reimagine your next chapter. 

That almost never works. 

You need time to rest. You need time to explore. To try things out. To become more creative again. To reimagine. 

When you are burned out and tired, your focus naturally narrows. You can only focus on the most essential and urgent things. That’s biology. If you don’t have enough mental resources, you should focus on surviving. If you’re lost in the woods, you shouldn’t be designing new buildings or writing a novel. Your 180-degree vision should shrink down to 20 or 30 degrees. Focus on the essential. 

But as you rest and recuperate, your vision can widen again. You can start to see new possibilities. You can think creatively. You can make connections you missed before. Your intuition comes back. 

I’ve coached dozens of people through this process, and the pattern is really consistent. But expecting to creatively and intuitively reimagine your life while you are buried at work is a lie. It’s almost biologically impossible. 

As you reimagine this next chapter, think about the roads not taken. All the paths that you could have gone down but didn’t make sense at the time. Maybe now is the right time? 

Is it too late?

This is a question I get a lot? Is it too late to start something new for a 2nd chapter? 

Here’s a rule of thumb I use when traveling. I need to spend 2x as much time in my destination as it takes to travel there. So if the drive is 2 hours each way (4 hours total), I want to be able to spend at least 8 hours there. 

Maybe that rule of thumb will help you decide if you have enough time. If you have always wanted to be a teacher and it will take 4 years of education, do you have 8 years of teaching left in you? 

The exception to the rule is if you love the journey to your goal. Would you love the process? Maybe the journey is even better than the destination. We live close to Glacier National Park in Montana. And we break that rule of thumb to go into the park all the time. Why? I love the drive into the park. It’s beautiful and relaxing. I’d happily drive the 2 hours total, even if we are only there for an hour.

Seven years ago I became financially independent, and I asked myself about roads not taken. There were many! Lots of things that felt to impractical, undependable, and risky during my 20’s. Things I passed by for more consistent paychecks. For the last 7 years, I’ve looped back to many of those old dreams. I started a coaching business. I wrote a book. I created online content. And I traveled around the country with our 5 kids. 

What will the next 7 years hold? That’s the biggest error in early retirement planning… assuming every year will be the same for the next 40 years. Once you are FI and in control of your time, the years become long. You can accomplish so many things. And you get to keep asking yourself the same questions and expecting new answers. Because life will change. You will change. And roads not taken before might be able to loop back around.