It’s a weird experience when you talk to others about financial independence and the potential to retire. For some, it’s such a foreign concept they simply don’t believe it can really happen. That’s fine.
For those who believe you might actually do it – it’s even stranger. They immediately assume that you plan to sit around and do nothing.
“I’d be so bored.”
“I’d feel bad not contributing”
“I wouldn’t know what to do with myself.”
There is a belief that early retirement means choosing to do nothing. That somehow we’d step away and life would become easy and purposeless. Maybe that’s true for some, but it’s not my purpose.
For someone who has had constant challenge, sometimes by choice other times not, this is both perplexing…and alluring. I want challenge in my life – I just want the power to choose. At least as much as possible.
Challenge Is Important
Challenge is important to progress. Virtually all of my personal growth has come as a result of struggle. There are powerful benefits to productive struggle.
Skill
Skill doesn’t come from repeating an already mastered action over and over. Repetition is important, but growth comes from working just beyond your current skill level. In learning, this is the zone of proximal development.
If you want to get better at something, you have to challenge yourself. Face a more skilled opponent, set your goals a little farther ahead, or take on a task you aren’t sure you can complete.
Each of these things will make you better. They don’t happen without challenge.
Awareness
Challenge brings a heightened sense of awareness. An alertness that is lacking when going through the motions. It can be an exhilarating feeling.
You have to pay attention, otherwise you fail. The world seems more vibrant and more real when you’re working outside your comfort zone.
Preconceived Notions
Experiencing challenge, well..challenges, your preconceived notions. Maybe you thought that job was easy – until you tried it.
Maybe your assumptions about why someone failed are flat wrong. The most judgmental people I see make assumptions about others when they’ve never faced similar circumstances.
Facing real challenge, whether you fail or succeed, lets you understand the possibility of failure better. The factors that lead to success or the very real barriers aren’t as obvious as you may think. It’s a growth experience for everyone.
Accomplishment

The feeling you get from overcoming something you, or others, thought was impossible is a hell of a drug. There are people who run entirely on resentment of being counted out or underestimated.
That doesn’t motivate me in the same way, but setting a goal and accomplishing it is an amazing feeling. (I’m working on untangling that from my perfectionism)
I can’t imagine choosing a life where I don’t have that feeling regularly.
I Just Want To Choose
Here’s the thing though – while all of those positives about challenge are true, there is an important caveat. Not all challenge is productive.
Some is toxic. Sometimes the costs outweigh the benefits. Sometimes the ability to overcome the challenge isn’t actually in your sphere of control.
I feel incredibly lucky that I’ve been able to overcome most challenges in my life. That many of those challenges were by choice. Yet, enough weren’t that I recognize the privilege inherent in being able to choose.
When is challenge not an ideal state? What challenges would I eliminate?
Externally Imposed
Challenges that come from a circumstance beyond your control often aren’t productive. Yes, you can often learn from them. Sometimes that lesson comes at a great cost. Other times, it’s a challenge that can be overcome but doesn’t confer any of the benefits I’ve listed.
I’ve seen toxic bullying destroy kids. Health challenges drain the life from once joyful people. Poverty pulls brilliant and driven people away from their dreams.
Yes, overcoming those things can be empowering – but people don’t seek them out. I’ve been poor, but I don’t want the challenge of overcoming financial insecurity again.
Work is the most common force applying externally imposed challenges. It’s one reason early retirement is appealing to many.
Other People
A huge part of my job is helping adults deal with their challenges. I’m willing to do it because I’m mission driven. Early on, I grew in skill by learning strategies for managing conflict.
That growth is in the past, and I get no sense of accomplishment from helping adults navigate their conflict.
Now it’s just one of the costs I pay because I want to help as many kids as possible. Worth it – but it’s not a productive challenge for me.
To be clear – I don’t want to eliminate supporting others. I’d just prefer to narrow the scope a bit.
Not Aligned With Goals
Challenge is great when it’s aligned with goals you want to achieve. Unfortunately, work challenges often do not. This is the nature of working as part of an organization – even when your mission is aligned it won’t necessarily align with your personal goals. Sometimes overall progress requires a different direction.
After twenty years in education, I’ve grown an incredible amount professionally. I won’t pretend I’ll ever master the incredible complexity of teaching or of managing other people. Yet, I’ve learned a lot. Early on, these were my goals.
It’s natural that after two decades of work, most of my personal goals are no longer work related. Therefore, work related challenges aren’t as fulfilling as they used to be.
Stress
One of my favorite quotes:
“Working hard for something we don’t care about is called stress: Working hard for something we love is called passion.”
– Simon Sinek
Challenges that are imposed upon you, or do not align with your goals, create stress. Surmounting these is still worthwhile, but is not fulfilling in the same way.
Similarly, externally imposed challenges often create stress. Financial stress, physical stress, mental stress.
How much better is it to experience challenges in areas you care deeply about, that you’ve chosen to pursue? Where rather than stress, you feel a drive to push through the challenge for something you’re passionate about?
No – You Cannot Choose All Challenge Or Eliminate Stress
It’s foolish to think you can choose every challenge in your life. That life will ever be stress free. In my experience, the moment things feel like they’re on cruise control something will knock you off.
Whether it’s health, family stress, or relationship challenge – something will appear that must be dealt with in order to move forward or simply survive.
I’m not naive enough to think financial independence will eliminate all hardship. Instead, it will provide more bandwidth to deal with externally imposed challenges. It can help smooth the bumps that we all experience.
And, in between those moments, it may enable you to choose the challenges you want to pursue.
What Challenges Will I Choose?
As someone with a strong bias for action, part of my challenge (ha!) will be limiting the number I choose. When I walk away from the career I feel passionate about but overwhelmed with, I don’t want to create a new level of “too busy.”
I love the idea of carefully curating where I focus my energy for maximum progress. I can predict where that will be when I first step away from work, but know it will evolve over time.
My early choices will be:
Fitness – Right now it’s a challenge to just maintain a base level of health. Many of the happiest times in my life have come when pursuing a challenging fitness goal – increasing my PFT score in the Marine Corps, preparing for a long bike tour, or training to ride up Haleakala are just a few examples. I look forward to setting an aggressive goal that requires me to train for long periods of time. It’s a luxury my current work schedule doesn’t allow.
Language – I’ve always been a strong student, easily mastering most academic areas with one exception: foreign language. It takes a significant amount of mental energy for me, in a way no other subject or task does. As a result, while I’ve dabbled in several languages over the years I’ve never taken the time to truly master one. That’s a worthwhile challenge.
Online skill – I’m getting older. At one point, I was on the front edge of technology. My chosen profession pulled me out of that world. I’d love to have the time and energy to challenge myself by learning a new skill in a world that is now largely unknown to me. Perhaps a programming language, graphic design, or something else entirely.
Financial Independence Lets You Choose (More of) Your Challenges

I seek financial independence to have more control. We embrace FIOR (financial independence optional retirement) because we may, or may not retire early – but we want the choice.
Those who assume financial independence is about eliminating challenge are wrong – at least in my case.
I want to struggle, to grow, to have my assumptions challenged, and to feel that amazing sense of accomplishment.
I want to pursue challenges that move me forward, don’t rely on other people, and ultimately bring me closer to whatever goals I set.
Challenge is great. I just want to choose.
How about you? If you had the luxury of choosing your challenges, which would you eliminate and which would you add?
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