How Alcoholism & COVID-19 Led Me to More Meaningful Money Values & A Vision for Financial Freedom

“We generally change ourselves for one of two reasons: inspiration or desperation.” So said the late Jim Rohn, one of the most quotable entrepreneurs and motivational speakers in American history.

Well, desperation drove most of my life changes, up til my mid-twenties. That’s when my secret double life of alcoholism and suicidal depression came crashing down on me. Finally desperate enough to come crawling into a recovery meeting with my tail between my legs, after 15 years of trying to stop the train wreck on my own, I was completely out of other ideas. Wrestling with the bleak state of my soul, I’d “tried everything,” and “nothing worked.”

The thing is, according to worldly standards, I had it made. It should’ve been one of the greatest “rags to riches” stories ever told! After growing up below the poverty line in small-town South Dakota, I turned 18 and started landing amazing city-job opportunities in fields I knew nothing about. (That's a whole 'nother post for a different day...) Given a journalism role I’d done nothing yet to deserve, I picked up the greatest life hack of all time: become a writer. There are no qualifications for becoming a writer, you see; writers just write. Our experiences are our expertise.

So, before I was even old enough to legally drink, my trajectory was set for a 10-year, hellbent crusade to make a name for myself in media and publishing. In years to come, I’d serve as an author, editor, and marketer of many things, fiction and non. The track took me from newspaper reporting to regional magazine editing to digital media strategy to co-founding a multi-continental book company. When I look back, I still have a hard time believing any of it myself.

By age 24, I was writing for international audiences, traveling the world for work and getting paid to take tequila shots with millionaires in Mexico. I should’ve been living my dream life—but a lifetime of dysfunction ate constantly at my soul, and I was dying inside.

Have you ever heard of cognitive dissonance? How about imposter syndrome? Google ’em. They defined the life I lived at the time.

In one version of reality, the world saw a talented, upwardly mobile young professional woman racking up awards for her publications and leveraging collaborative business partnerships across social media, back before the term social media even entered the vernacular. A nerd by nature, I taught myself to code, design websites, edit video, run Photoshop, set up Web campaigns… all from an old Compaq laptop in a corner of my bedroom late at night, while a rural South Dakota town of 120 people slumbered around me and my drug addict husband played Madden with his drug addict buddies in the living room right outside my door.

You see, everything I ever wanted to do, I learned from the internet—usually while “everyone else” stared at TV screens and accused me of being a weirdo, a freak, or a know-it-all. Thus, the enduring identity crisis I brought into my adulthood... In my work, I was highly valued for what I knew, what I could do, and what I had to say. In my white-trash-reject personal life, however, I was belittled, scorned, and dragged down for “always tryna be better than the rest of us.” Truthfully, I wanted all of us to be better—but I couldn’t do it for everybody. Not by myself.

And no matter how hard I pushed myself or how far I went in my work, eventually, I always had to go home again. That’s where the “other” me lived—the one shrinking under the crushing pressures of addiction, abuse, and abandonment, weighing down every single branch of my family tree.

I didn't know how to break free. I knew there was something more out there—I'd read enough books and rubbed elbows with enough people on business travel who were living the kind of meaningful life I sensed possible. But nobody in my small-town South Dakota personal circle wanted any part of it (or at least, they didn't want to put in any effort for it), and I didn't know anybody locally who did.

As far as worldly achievements went, I’d overcome bizarre levels of adversity and disadvantage, taking a drastic jump up the ladder right out of high school, without even trying. But the money, the accomplishments, and the impressive résumé didn't fill the hole in my soul. I kept looking to the people closest to me to do that, but they just used me and ditched me without a second thought. No matter how much talent, skill, and ambition I brought to my work life, nothing I did could stem the bleeding from home.

By age 26, I had no integrity left—no nerve to live up to my own values in the midst of my moral decay. Just like when I was a kid growing up on the wrong side of the tracks, I could see that a certain kind of life was available to other people, but not me. My spirit railed and wept; I was blackout drinking almost every night and hoping I wouldn't wake up in the morning. I started cutting myself and wrecking vehicles out on country gravel roads. Even if nobody around me could see the problem, I knew I was a fraud, and it was killing me from the inside out.

Grant me the serenity... to accept the things I cannot change, courage to change the things I can, and wisdom to know the difference...

Friends in recovery will recognize this meditation intimately. It’s a hallmark of every 12-Step group which purposes to address any addiction or compulsion. Back when I hit rock bottom and finally attended my first recovery meeting, somewhere in between these words, I mumbled my way into a private dialogue that began to radically reorient my entire attitude and outlook on the world around me.

My life didn’t change instantaneously... but in a way, it did. In one breath, I left behind a person who saw only failure, and in the next, I became a person who could see hope.

Over the course of the next year, I lost everything I ever had and found everything I was always missing. I lost a career, a marriage, and a house, in that order. I experienced incarceration, divorce, bankruptcy, foreclosure, and homelessness. By the end of the whole mess, I was down to a dog and a pickup truck—sleeping on my mom’s cigarette-burned couch in an abandoned old farmhouse, starting over as a bartender in a seedy rural joint 15 miles away, since that was the quickest and easiest way I knew to get my hands on some money while I figured out how to be sober.

As awful as that year was... I was alive again. My life was falling apart all around me, and I’d never felt better.

Why? For the first time in my life, I was making meaningful, intentional choices about what mattered to me and how I would live. Yes, even bartending for a living while getting sober from alcohol—that, too, had its place in time. It was a calculated compromise I made with myself, a decision I made on purpose, as a bridge to my next action steps. Uniquely, after I saw everything taken away from me, I got to be the one to decide what I would add back in. There I was, a twenty-something has-been, and life had just begun.

Since then, everything has changed. It’s been a little over 10 years, and inspiration—not desperation—continues to be my reason for change. There was a time when I didn’t plan to see age 30; I’m 36 now, and I have so much to live for.

In many respects, The Serenity Project has been under way for a little over 10 years now—a work in progress; a life reverse engineered to its proper function. Who knows if I’ll ever have time to tell the whole story?

The thing is, I’ve spent at least five of those years wanting to give back what I’ve been given, looking for a way to start. It took a global pandemic and a year of “2020 Vision” to see where I’m going from here. Writers just write.

Looking back on my former life as a workaholic desperate to escape my past, I can see my struggles to embrace my identity apart from what I could "do," understanding my value only in terms of what other people thought they could get out of me. Throughout 2020 in particular, and all through the COVID-19 crisis, as so much of "business as usual" has been disrupted, I’ve been reflecting on my relationship with money, work, and self. Like so many other people, I’ve spent this past year asking...

• What really matters?
• What is my life focused on?
• What am I building, and what am I leaving behind?

Around this time last year, as our world collectively experienced a forced "slowing season," I found myself reflecting about what drives us, what calls us, what inspires us to do the things we do... the yearnings and desires that long together in us to make a difference, to somehow matter. I spent hours in my journal, observing the outgrowth into our enduring inner power struggles—self-defeating conflicts between creativity, responsibility, rhythms of work and rest. Somewhere along the way, I began to lean into a liberating, countercultural design for human flourishing that smiles in the face of our common, compulsive instinct to impose rigid control.

I really didn’t expect to begin 2021 setting out on an investing experiment or aiming for financial freedom by age 50. But somehow, after the year we’ve all just been through, nothing seems impossible. All of a sudden, becoming a millionaire doesn’t sound that hard. Living off of investment income seems surprisingly realistic. Financial independence and early retirement look fairly doable. Maybe that’s not a big deal for some people, but if you knew the life I've lived, you’d understand why these prospects should feel so absurdly far out of my reach.

I have no idea what will happen. It’s an experiment. I have no particular urge to get rich, exactly. I want to experience financial freedom. I want to live generously. I want to give extravagantly. I want to spend my days enjoying one moment at a time.

I want to test out this hypothesis that being “reasonably happy in this life” can be possible for anyone, even me. Asking, "What really matters?" in the great scheme of things, I’m finding all my other priorities falling into their proper place. And from there, the sky’s the limit.

Alongside some serious soul-searching this past year, examining these warring demands between creativity, responsibility, rhythms of work and rest… I’m seeing that the concept of financial freedom carries many more far-reaching implications than those numbered solely in dollars and cents.

I don’t know about you, but I’ve got a lifetime of baggage and breakthroughs to sort out along the way… letting go of limiting beliefs, and the lies that hold us back from what our souls sense is possible.

What do you think? Have we got the courage to change all the things we can? Well, that brings us to The Serenity Project—an experiment in winning the wealth-building game.

In the year ahead, I plan to continue writing about my experiences as a beginner investor, using the Stash app to build a portfolio in the stock market. I’m not saying you should do it, too—I’m just gonna try it myself and let you know what happens. I’m learning as I go, so if you’d like to come along for the ride, we’ll be learning together, hopefully doing our small part to turn the tables and win the wealth-building game, for the good of greater society.

Does that sound overly ambitious to you? Maybe we just haven't allowed ourselves to think big enough before.

If you like anything you read here, please share this post with your social media networks to get more people thinking about how we can all start winning the wealth-building game. Like to connect? Drop me a line: jeanmillersays {at} gmail.com.