The Number One Most Crucial Step To Following Your Dreams And Living Out Your Passion

My least favorite piece of career advice read:

Do what you love and the money will follow...

It’s not exactly an outright lie, but it’s misleading, nonetheless.

The truth is closer to this:

Do what you love. When you do what you love, it's more likely that you will do it well. If you do it well (assuming that what you do is of value to others), you may be able to get paid for doing it. And, between the time you start working at what you love and are able to support yourself doing it, you will likely have to do some other work that you don’t like as much to pay your bills. And, though you may never get rich, waking up every day and doing work you enjoy is still better than making lots of money at a job you hate.

How does that sound? Sorry if it's different from the advice you've been given, but my intention is not to throw cold water on your dreams. I just want you to go into this with your eyes wide open; I don’t want you to make decisions you might regret.

More accurately, I want you to learn from my experience and do a better job executing the transition from an unfulfilling corporate job to a life you love. Here’s how:

Living the dream

I decided I was going to "do what I love" on a beautiful September day in New York City. It wasn't just any beautiful September day in Manhattan; it was September 11, 2001. Soon after making my personal proclamation, airplanes hit the World Trade Center and Pentagon and changed the world forever.

At the time, I was working for a small magazine publishing company. The work wasn't soul crushing, but it wasn’t what I wanted to be doing. I had previously been too scared to act on the advice about doing what you love and believing the money would follow. I was too afraid of what others would think; afraid of “falling behind” my college peers and totally f*cking up my life, among other things.

However, that September morning, everything changed. Amidst the noisy chaos and confusion of the day, I felt like the Universe was sending me a quiet message that life is too short to not start living it today.

And so, I started. Three days later, I officially quit my job and three weeks later, I was in my car, heading west to Aspen, Colorado to do what I loved: ski.

I had always loved the idea of life in a ski town. I loved the idea of waking up every day, invigorated with the sight and smell and feel of the mountains. I loved the idea of how I would feel getting paid to share my love of skiing with men and women from all over the world. I love the idea of the people I would meet, the friendships I would form and the stories I would tell.

In many ways, the idea of life in a ski town was just as good, if not better, than I had imagined. The mountains were intoxicating. Teaching skiing was insanely fun. The friendships I formed were amazing. The stories we told often prompted my friends and family back East to simply say, “Wow, you are really living the dream.”

In many ways, I was. But, many of friends back home didn’t fully appreciate that in order to afford my “dream,” I was working my ass off and just barely getting by. I was doing what I loved, but the money wasn’t following.

Paying for the dream

My first year in Aspen, I taught skiing part-time (a typical first step for a new instructor). While experienced, certified ski instructors can make upwards of $40 per hour teaching, “rookies” start at around $8 per hour. Needless to say, my paycheck wasn’t cutting it.

After a long search for a second job, I finally got an offer to bartend at a fancy local hotel. (In a ski town, any bartending job is a good one.) But, just like on the ski slopes, the new guys typically make less than the experienced pros.

In my first year bartending, I earned roughly $20 per hour, including tips. In addition to taking on a second job, I also committed to living cheaply. I shared a condo with three other ski instructors and I resisted the (excruciating) temptation to buy new ski equipment.

I often ate a breakfast of coffee and a Clif Bar, as both were provided free to ski guests (or employees) on the mountain.

No-regret personal finance

According to my tax return, I made just over $20,000 that first year in Colorado.

Sure, it wasn’t much. The money didn’t “follow,” exactly as I thought it would, but it was enough. I never had to ask family or friends for money. I was now paying my own way. Ultimately, I lived and worked in Aspen for four years and I wouldn’t trade that time or experience for anything in the world.

That said, when people today seek my advice regarding quitting an uninspiring job and following a “passion,” whether it be teaching skiing in Colorado or starting a new non-profit, my advice is always the same: First, figure out the money.

Specifically, I recommend abiding by the following three personal finance guidelines to ensure that, even if the money doesn’t follow exactly as you hope, you’ll be able to keep doing what you love:

1. Stay Cash Flow Positive

The freedom to do work we love requires that we stay cash flow positive; in other words, we must spend less than we earn.

Before you quit your job, consider how much your lifestyle costs. How much will it cost you to move? How much will you need to make to afford your new life? Despite making far less money, my cash flow position improved when I moved from Manhattan to Aspen, due to a significantly lower cost of living.

2. Fill Your Freedom Fund

The “Freedom Fund” (aka “Emergency Savings” or “Rainy Day Fund”) is a secure savings account that equals six to 12 months of living expenses. The fact is, sh*t happens: bad jobs, bad relationships and bad luck. The Freedom Fund guarantees that we can survive and escape from bad situations and continue to do what we love.

What I didn’t realize when I moved to Colorado was that while the ski season starts around Thanksgiving, you won’t actually make “real” money until Christmas. My “Freedom Fund” gave me the cushion I needed to get through the lean months.

3. Get Protected

There is no greater threat to your financial wellbeing and/or ability to do work you love than an uninsured emergency catastrophe. Whether you are teaching scuba in Santorini or making micro-loans in Somalia, everyone needs two types of protection: health insurance and renter’s insurance.

Today, health insurance is available to everyone. Don't think twice about this. Nerd Wallet Health estimates that more than 10 million people will not be able to afford basic necessities, such as food, rent and heat, due to medical bills. This is the fast track to a life you won’t love. Protect yourself.

Renter’s insurance is an inexpensive (about $12 per month) policy that protects you and your stuff in the event of fire, flood, theft or otherwise bad living situation catastrophe.

When investigating Renter’s coverage, be sure to read the policy for the specifics of what’s covered and what’s not. If something isn’t explicitly stated as covered, assume that it’s not. A little research is all you need to find a policy that’s best for you and your situation.


So, are still fired up to do what you love?

I hope so.

There’s no better feeling in the world than waking up in the morning, psyched to go to work and to love what you have to do. While doing what you love may never yield a crazy financial windfall, if you follow the simple steps above, you should be able to keep doing it.

As far as I'm concerned, that really is what matters in the end.

Photo Courtesy: We Heart It