Going Confidently and Joyfully Rogue on the Path to Financial Independence

Back in March Mr. Money Mustache (MMM), probably the most well-known FIRE blogger, penned a post he titled Money and Confidence Are Interchangeable. In this article he gives some examples from his own life to make the case that a person who has enough confidence could quit a job s/he doesn’t like to pursue work s/he does enjoy and make enough money to live a comfortable, happy life. MMM notes that since many people lack this confidence they stick with a well-paying job that makes them miserable because they fear they’ll be unable to create sufficient income streams on their own doing work that’s meaningful to them.

I sense that my intrepid days as a Peace Corps volunteer and faith in my ability to always land on my feet have led me to be more adventuresome and confident than others. My version of pursuing financial independence would be fraught with fear for many others. I walked away from my last W-2 job in 2010. I was brave enough to approach my boss with the idea of using some of the grant funding I was helping the organization secure to hire me on as a part-time consultant after I left. That consulting work continued for three years until I realized that I was ready for a new adventure, one that involved more time outside and exploring new places. So I sold my house in DC, offloaded most of what I owned, and spent the next two years house-sitting, Couchsurfing, camping, and crashing with family out west. I did not work at all during this time. The only income I earned was on investments in my retirement accounts. I lived off of some savings and money earned from the sale of my house. I guess it was a mini-retirement of sorts inspired by reading The Four Hour Workweek by Tim Ferris.

At the end of my nomadic experience almost three years ago I bought a house and settled in St. Petersburg, FL paying cash with the money I had left from my DC house. In terms of income generation that mini-retirement still exists to some extent as I have yet to find ways of earning enough money (that also bring me joy) to steadily increase my net worth. I see myself currently as pursuing a cross between lean FI and entrepreneur FI. I house-hacked and got a roommate. After roommate rental income, my next largest influx of money comes from the still usable items I rescue from dumpsters and sell on eBay, Etsy, and Craigslist. I have a backyard plant nursery as well. And now I’ve started this blog. I’m still deliberating how I want to monetize it without pushing products and the extractive and predatory practices of many companies.

I so appreciate the sincere honesty and vulnerability Gwen from Fiery Millennials demonstrates in her recent post about the Entrepreneurial Slog she’s now experiencing after boldly leaving her W-2 job. I completely relate to a number of the points she makes in this post. Things haven’t gone as she planned since she left her job and now she’s considering part-time employment to fill the $$$ gap. I too figured that I would more easily and quickly identify a couple of high income generating (and meaningful to me) entrepreneurial activities that would have a more positive impact on my bottom line after settling in Florida. Like Gwen, my stagnant finances concern me some, but I retain my faith in myself to markedly improve the situation. (There’s always Barista FI, which is what it sounds like Gwen is going to pursue temporarily.)

I’ve veered even further off the mainstream FI path by pretty much eliminating low-cost broad based index funds and rental properties from my investment portfolio. I’m experimenting with a more conscious money approach, having moved most of my funds from my employer based retirement plans to a self-directed IRA. Now I’m investing in sustainably-minded businesses, a local farm, and hopefully soon some local businesses and other alternative investments I’m still learning about.

What I’ve outlined above may sound like an uncomfortable path to FI to many people. For me though, my days are filled with time outside, in my garden or on my bike; planning impromptu outings with my boyfriend; and volunteering with refugees amidst all of the income generation activities. For now my income is sufficient to cover most of my expenses and my income has increased from last year. I sense that trend will continue. I take a great deal of inspiration from Ernie Zelinski’s books The Joy of Not Working and Career Success Without a Job.

Knowing about the multiple forms of capital or wealth that surround me daily is also part of what gives me the confidence to hover tentatively at this somewhat floundering version of Entrepreneur FI (FIE) while I explore the best money generating matches for me. When I wanted the big shed moved in my backyard a dear neighbor and his son helped me do it for a fraction of what I would’ve paid somebody else. And they would have done it for free, but I didn’t feel right not giving them something for this job — it’s a big shed and there was a tree branch in the way. I make sure to share the abundance of organic produce I rescue from the dumpster of the local organic food store with this neighbor and many others — social capital in action. I can walk out my door and harvest pumpkins, garlic chives, and

sweet potatoes pretty much year round. In the summer there are avocados and longans to pick. I’m not likely to go hungry thanks to the living capital with which I’ve surrounded myself.

There’s so much abundance around us we just need to open our eyes to it. We can get so easily drawn to the scarcity mindset by mainstream media. We’ve all heard it – what we focus on increases. Think about it. When you are considering purchasing a new car, you start noticing that car everywhere you go. So why not focus more on abundance and less (or not at all) on scarcity? I think one of the most entertaining and motivating books, which touches on this is Jen Sincero’s You Are a Badass at Making Money. (I highly recommend the audio version which she reads herself. Her inflection and humor are spot on.)

A few other strategies that can help increase your confidence around achieving FI include:

Frugality — In a post last year, Liz from Frugalwoods catalogued 19 reasons frugality is the best thing that ever happened to her. See point number 17 to learn how her frugality led to increased confidence.

Enough — When people answer the question “what is enough?” for themselves they often recognize that it doesn’t involve as much spendy stuff as they originally thought.

Resourcefulness — The more we can do ourselves or tap our social capital to find ways to get others to help us do things without needing to pay them, the less money we will need to spend once we stop working a W-2 job.

And since we’ve been swearing in this post it seems apropos to mention Miss Mazuma’s latest article – Fuck it FI. In it she relates how windy her FI journey has been so far and will likely continue to be. Life happens! she exclaims. She’s confident enough to remain flexible with her “numbers and timelines and the outcome of everything” since it looks like she may not retire as early as she originally thought. Like Miss Mazuma I am confident and optimistic. Most of us contemplating financial independence already are intelligent, higher-achieving, resilient individuals, who think a little differently and can quickly pivot and recover when necessary.

What about you?

How confident are you on the path to FI?

What would you do if you were more confident?