This reader story comes from Joel Zaslofsky, who is offering instant access to download the free tools on his website Value of Simple to help you simplify, organize, and be money wise. When he’s not helping people start investing with $100, enjoying nature, podcasting, or chasing his sons around the house, he’s cranking out useful stuff at Value of Simple.

I was so stoked to go from $105,143.56 in annual compensation to $0.00 overnight.

This was in March 2012 as I quit my cushy corporate gig in the wealth management industry and became a full-time entrepreneur. I had – and still have – this deep passion to help people simplify, organize, and be money wise… and I took a leap of faith that this life transition that would somehow work out.

I didn’t leap alone, of course.

My wife Melinda took a giant emotional, mental, and financial leap too. The jump was swift, but the race to the ledge was slow. My transformation from soul-crushing corporate job to exhilarated solo entrepreneur was done in true Get Rich Slowly style by calculating, planning, and taking the long road.

It took almost two years and many conversations to trade my stable job for an uncertain life. And on my first glorious day of self-employment, I had no idea how to make money (and serious money avoidance issues from years of working for a purposeless paycheck).

My story is still unfolding, but I’ve journeyed long enough to share how to earn less than $25 a month for sixteen months and still be happy, married, passion-driven, and financially healthy.

I’m Not That Much of a Minimalist

I’ve strongly embraced minimalism since my personal renaissance began when my wife, Melinda, told me, “I’m pregnant!” with our first son, Grant.

But as much as I’ve simplified my personal finances and helped to reduce our family’s money needs, I’m locked into some big fixed bills. Like you, my mortgage, day care, groceries, utilities, home maintenance, car use, insurance, vet trips, and tax bills (among others) aren’t optional.

It helps that my recurring bootstrapped business bills are $78 a month, but that doesn’t count the thousands spent on:

  • Website development and graphic design
  • A marketing contractor
  • Trips to events like the World Domination Summit to hang out with J.D. and 2,998 other amazing people

My business has lost money from day one and only recently have I started to turn the corner. But this is what my net income looked like for sixteen thrilling and unsettling months between March 2012 – June 2013:

  • Products
    • Start Investing with $100: $201.17
    • The Digital Launch Playbook: $79.64
  • Services
    • Unsexy System Sessions: $24.17
  • Affiliate Marketing
    • Various: $86.13

So how does a person earn $391.11 over 16 months and have everything still be OK?

Saving + Support + Frugal = “We Can Do This!”

I knew I wanted to quit my job for something else – anything else – in May 2010. So I planted the self-employment seed with Melinda and worked with her for two years to get financially (and emotionally) prepared.

Little did I know, but we were already prepared from a decade of solid habits including:

  1. Prioritizing our long-term fiscal health by maxing out our 401(k) and Roth IRA annual contributions.
  2. Keeping strong bonds with a supportive community of family, friends, neighbors, and co-workers.
  3. Maintaining top credit scores to literally cash in on credit card sign-up bonuses and secure a 2.875 percent 15-year fixed-rate mortgage.
  4. Ensuring we had zero non-mortgage debt.

I had some other things going my way, though, to smooth the transition from six figures to zero figures. I’m grateful for friends who challenge me to live an intentional and meaningful life, for my sugar mama (a.k.a. Melinda), and a technology landscape to bootstrap my online work.

With the help of minimalism, learning from other people’s success stories, and my share of hard knocks, I gained some insight that I’d like to pay forward to you.

The lessons

I’ve absorbed a lot of knowledge since kicking my videogame addiction and starting my personal renaissance. And I’ve shared this insight with enough people on Value of Simple to know that they’re all important.

  1. It’s more vital that your kids are happy with spending less than unhappy in the empty pursuit of always earning more.
  2. Starting a micro-business is simple and requires little up-front investment. The work is still hard and the stress is still there, but awesome resources like Tyler Tervooren’s The Bootstrapper Guild or Courtney Carver’s Create a Microbusiness can help.
  3. Take smart risks when they present themselves. I snapped up an offer for steady contracting work from a friend to be her business “Billing Support Guy,” even though I risked diluting the time for my business in the process. It turns out that working on her business doesn’t detract from my business and that I was offered the gig because of my “give first, give second” philosophy. That reminds me…
  4. Living generously makes everyone else happier (including you). Making a positive impact in other people’s lives is where I find meaning these days. And doing most of it for free through my website, podcast, the Refuge of Simplicity, and other creative resources excites the hell out of me!

But perhaps the biggest lesson I’ve learned is that the opportunity costs are more important than the financial costs.

I’m confident that I’ll earn more over a lifetime of self-employment than I would have in my corporate job. Some people find purpose, success, and happiness in working for someone else, but that just wasn’t for me.

As sales of my products and services grow, I get tremendous joy from being a fully present papa and husband. And my ability to pass along health, gratitude, and personal finance savvy to countless people has me beaming like the sun’s rays.

So how about you?

Have you ever had a personal renaissance that changed everything? What lessons have you learned about structuring your life without chasing money like a dog chases a car?

This article is about Budgeting, Career, Entrepreneurship, Reader Stories