Since I’d never have you try something I haven’t applied extensively in my own life, later I’ll be sharing with you the story of how I used these very tools to go from being broke, miserable, and desperate to building my own dream career for myself, which is both meaningful to me and lucrative. But for now, let’s dive into the Four Steps to Aligning Your Money and Your Meaning directly.
There are three groups of people I’ll be talking to in this section:
A) You’d be happy spending the rest of your life earning what you’re now earning, if what you’re doing now felt meaningful to you, but it doesn’t.
B) You’d be happy spending the rest of your life doing what you’re doing because it feels so meaningful to you, but you’re not earning enough money doing it.
C) You’re not happy with either the money you’re earning or the meaning of what you’re doing to earn it. In other words, Shit City.
I’m going to address people in groups B and C first; I’ll address group A in a moment.
STEP 1: Get on Your Feet Financially
If you’re in group B or C, there’s really only one thing to do next. Get on your feet financially. I was in group B big-time during my “wannabe literary bad boy” phase, for much of my twenties, which I’ll describe later in this chapter. I could have happily gone on for the rest of my life writing that stuff (God save the readers!), but the money simply wasn’t good enough for me; there was no money.
If you’re in group B or C, get on your feet financially, however you can. That’s what most of the people in this book did. They got financially stable, from a young age, often their mid-teens. Get a square job, a corporate job, a temp job, a boring nine-to-five. Don’t feel anything is “beneath you” so long as it pays. Wait tables if you have to. Give up your “art,” “purpose,” or “meaning” for a little while and know what it means to be financially stable. Get a kinesthetic feeling in your body of how it feels to have enough money to pay rent, to pay your bills on time, to take your sweetie out to a nice restaurant.
The best way to get financially stable, once you have some kind of job—any job—is to exhibit the entrepreneurial leadership values on the job, described in detail in Chapter 7, “The Entrepreneurial Mind-set versus the Employee Mind-set.” This is how I did it and how all the self-educated entrepreneurs in this book did it.
STEP 2: Create More Room for Experimentation
This step (and all the rest) applies to groups A, B, and C mentioned above. (Presumably those in group A are already financially stable and thus have already completed Step 1.) The next step in Aligning Your Money and Your Meaning, once you’re financially on your feet, is to create more room for experimentation.
Finding a comfortable meeting ground for your money and your meaning is going to require a lot of experimentation. Experimentation takes time. It takes money. And it takes room to fall and to fail.
Having the financial stability gained in Step 1 makes it a lot easier to start taking some measured risks in your life. Anthony Sandberg, for example, started his sailing school when he already had money coming in from his solar and plumbing business. Elliott Bisnow, whom we’ll be meeting in Chapter 2, started his Summit Series when he already had money coming in from his real estate newsletter business. My wife, Jena, worked a variety of unfulfilling jobs before she developed her health-coaching and yoga-teaching career, which was more fulfilling to her. And again, she waited until she had solid money coming in from her health coaching and yoga before she took the next step and opened a wellness center. Frank Kern, whom we’ll meet in Success Skill #3, worked a variety of shit jobs as he was building his Internet marketing business.
It’s just so different—and better—figuring out how to make a difference in the world and find meaning in your life when your bills are covered and you have a secure roof over your head. It’s way less stressful than trying to do it when you’re broke. And, once the hurdle of supporting yourself is already passed, you’ll be much less likely to take a path that leads you to being broke again. Paying your bills on time is a seductive feeling, and once you get in the habit of it, you won’t want to go back.
Now, one problem you may encounter once you’re financially stable is that the time it takes to create that financial stability in your life is so great, there’s nothing left over for anything but following the dictates of your job. This is where Step 2 comes in.
You need to free up time and space for some experiments in leadership, innovation, making a difference, and finding meaning. If you’re working freelance gigs (as I was during this period), then there’s always a way to find a few spare hours each day for starting a pursuit that might feel meaningful to you. If you’re working seventy-hour weeks at a corporate job, however, there will be very little space left over for anything else but that.
In this case, you should begin taking some risks at work. See if you can get buy-in from your boss to focus more on results you achieve, rather than focusing on hours logged. There are some great books on how to make this transition, including Why Work Sucks and How to Fix It: No Schedules, No Meetings, No Joke, the Simple Change That Can Make Your Job Terrific by Cali Ressler and Jodi Thompson; Chapter 12 of Tim Ferriss’s The Four-Hour Workweek, titled “Disappearing Act: How to Escape the Office”; and also The Custom-Fit Workplace: Choose When, Where, and How to Work and Boost Your Bottom Line by Joan Blades and Nanette Fondas.
Flextime, working at home, telecommuting, working from your laptop and your mobile phone—these just aren’t the foreign concepts they were even five years ago. There’s really no excuse for not creating some flexibility in your workday now if you want it. The only excuse is your own fear and lack of imagination—and those aren’t good enough.
STEP 3: With This New Space in Your Workday, Begin Experimenting!
With some increased flexibility in your workday and workweek, or at least some buy-in from your boss about the idea of getting evaluated based on results rather than hours, you can now experiment with taking some risks toward making a difference within your organization, workplace, or industry. Read Chapter 7, and adopt an entrepreneurial mind-set at your workplace. Solve problems that you weren’t “hired” to solve. Contribute in high-leverage ways you weren’t hired to contribute. Leading always feels more meaningful, impactful, and creative than following.
Read Seth Godin’s Linchpin: Are You Indispensable? This is the best book I know on the topic of exercising more leadership within your organization—which Seth calls being a “Linchpin”—no matter what your formal title or job description is. Become a Linchpin in your organization. Most of the people featured in The Education of Millionaires worked their way up their early jobs by doing so even if they’d never heard of Seth Godin.
If you’re already working in the field you plan to stay in for the rest of your life, and you don’t want to become an entrepreneur within that field, then you’re right where you need to be in the Art of Earning a Living. Keep seeking out opportunities to exercise more leadership in your workplace (read Chapter 7 and apply the entrepreneurial mind-set at your workplace). Keep looking for ways to stick your neck out, to take risks, to innovate, to make a difference, in the name of taking your organization to the next level.
With the newly flexible hours in your day and week (from Step 2 here), you can also begin experimenting more intensively with potential sources of meaning, passion, and purpose outside of work, from artistic endeavors to charity and causes.
Many people are quite content to leave things here: they have a career that pays the bills and in which they’re increasingly making a difference and finding meaning, through exercising leadership. And they also have time during their day or week to pursue meaningful passions outside of work.
Seth Godin recommends this path for many people. He told me: “For fifty thousand years, humans did what they were passionate about, and then they did something else to eat. I don’t think there’s anything written down to say that those days are gone forever. We don’t have a poetry shortage. There’s plenty of poetry. No one gets paid to write poetry. If you want to write poetry, write poetry.”
There’s really not much downside to this path. It works. Worst case, you have a day job that pays the bills with increasing artistry, creativity, and leadership, and you get to explore your passions (for poetry, singing-songwriting, charity, etc.) on the side.
STEP 4: Striking Out on Your Own (for Those Who Want to Change Careers, Become Entrepreneurs, or Become Self-Employed)
If your current field, industry, company, or organization does not reflect your deepest sense of purpose and meaning, then you’re going to need to go beyond Step 3 in Aligning Your Money and Your Meaning. You don’t want your passion and meaning to come either from your current job or organization, or “on the side”—you want to find a new main dish. With the flexible hours in your day and week gained in Steps 2 and 3, begin experimenting with things that might one day become both a source of meaning and a source of serious income for you outside of your current job.
This might mean starting a small business on the side, moonlighting in a second “start-up” career, pursuing self-study to prepare for a different career, or finding ways to earn money from your artistic and creative passions.
Whatever it may be, if you want to make a living from it and leave your current job, you’re going to have to do a deep dive into the success skills in this book, particularly marketing, sales, and networking. You’re going to have to wrap your own passions, talents, and purpose—the things you care most about and are best at—in the package of these fundamental success skills. If you know how to do that, you get paid a lot, and you’re living your passion and purpose. Keep reading. A major pitfall in this journey is that we are so conditioned to thinking of money and meaning as separate, we overlook creative ways that we can bring them together. If you use your noggin—and the success skills in this book—you can find a zillion ways to interface your creative skills, passions, visions, and dreams with the already-existing worlds of capitalism and commerce. I’m not going to say this will be an easy or risk-free task. However, the stories throughout this book should provide plenty of examples and inspiration of how to do it.
As I was interviewing Seth Godin (who went to Tufts and got an MBA from Stanford), we were sitting in the main dining room of the architecturally stunning Capital Grille on Forty-second Street in Manhattan. Seth told me:
“People have this idea that either you’re a cog in the machine, just working for the man, or you’re out singing onstage, making your living that way. It seems like there’s a lot in between—there are a lot of people who may not have what it takes to become the next famous musician, but who are finding ways to make money with what they care about.
“Think about this restaurant right now. It’s not really like any restaurant in New York City that I’ve ever been in. Where did it come from? It’s not here because someone made chairs or china, which are available to everyone. It’s here because someone’s putting on a show. And they’re charging many times what they would get if they were selling it from a street cart.
“I’m saying that’s ‘art.’ Someone didn’t just copy it. Someone had to take various components and put them together, to create something that was worth experiencing, and sharing, and talking about. On the back of that, you can build a business that makes tons of money selling food.
“The art here, the experience of seeing it, that’s free. Anyone can walk in this place, look around, get it, and leave. The souvenir part—the experience part, the owning-the-table-for-two-hours part—that’s what they make money from.
“McDonald’s fooled us into believing that the purpose of industry was to churn out standardized quantity at low cost. This place reminds us that, no, there’s an alternative to racing to the bottom. And that is, racing to the top.”
Are you ready to race toward the top and combine money with meaning? Keep reading—the remaining stories and skills in this book show you how.
Next: Portrait of the Artist as a Young Fuckup: How I Went from a Broke, Miserable Wannabe Superstar to Financially Secure, Creatively Engaged Professional Author
