As I’ve gotten older, I’ve become more and more of a seeker. This must be a commonly shared trait across many verticals of my identity—millennials, entrepreneurs, single parents, independents, and all of those for whom life is a little variable, capricious, and unconventional. The purpose of all of this questing, seeking, and exploring is ostensibly to define and identify my “passion.” My Passion. Thee Passion Of Thee Meg. My True Calling™. I mean, every conference I’ve been to, every book I have read for self-starters and founders and aspiring trailblazers, and all the interviews I’ve seen with my heroes in the pursuit of happiness have made sure to repeat that axiom enough to convince us not only of the authors' magnificent self-assuredness, but of the imperative necessity to life of being able to define and name that elusive True Passion. “Do what you love, and you’ll never work a day in your life,” right? It’s almost haunting—what if I don’t find what I love? What if I can’t do it? And, hold on. Who the hell doesn’t work a day in their lives?
I think we all need to loosen the reins on the idea that success and happiness, in practice, looks like sacrificing everything conventional and redeeming it for a fountain of wealth and free time. The pressure we put on ourselves to give up our jobs and savings and die for what we do is so overwhelming and unrealistic. The truth is that no one really finds success “following their passion” without a practical plan, lots of discipline, and a little luck. Small steps are the first part of the plan. You can take them without giving everything up, taking out a big loan, or even quitting your job. I first heard Jason Fried say “Failure is overrated." Jumping off a cliff without a parachute is not actually a rite of passage for entrepreneurs. But, I think a false start is still a start--when founding something new, it's not a choice between "giving up everything" and "never beginning at all." So there's no glory in going down in flames. Cashing out every safety net you have to start something that may not even have enough value to be sustainable is one of the most common ways new entrepreneurs undermine their potential for success.
It gave me a lot of relief when I realized that maybe the way to happiness wasn’t defining my passion, but honing my skills. Getting good at things I liked, to put it simply. I like lots of things. I like to embroider and sew. I like style and fashion. I like to read. I like to support people who create things. I like making little websites. I like thinking about beauty, finding it, and showing it in the world. I like discussing issues of justice and equality and civic progress. I love to bask in controversy. So everything I do in my life is caused by or related to or informed by these interests of mine, and that’s why I don’t just do one thing.
By focusing on the intersection between what I like and what I am skilled at, the feeling of fulfillment that comes from “following passion” began to emerge and become easier to identify. Over time I began to find overlap between what I was interested in doing and what people were willing to pay for. Ten years ago I was embroidering flowers full-time, which turned gradually into a thousand different things to bring me to owning a women’s clothing startup today. I got here by following where my skills led me. Skills evolve. Opportunities emerge. And then we see our passions—what brings us purpose, personally—with more clarity. With self-awareness and intentional self-development, it’s a cycle that continues to redefine us all the time.
My passion is just being free. That’s why I do all this.
What my partner Sarah and I are building with Hello Holiday is really exciting, and it’s important to both of us that we build something sustainable. My clearly stated goal has always been to get to the point where I can travel most of the time, work remotely, write more books, do more speaking engagements, and mentor others eventually as an investor and venture capitalist. But to get to that point, we need to sell some shit. And she and I need to be working together to do that, whether that's Sarah's basement, in a rented loft apartment above a bar, in a downtown coworking space, or in our own showroom. We’ve come up through all of those places, and we would go back to any of them if we had to. All I'm ultimately in pursuit of is simply the freedom to do this massively fulfilling and fun work.
So that's how it is. And then at night, when I'm done with the office, when the door is locked and the lights are off, I write these things. That’s what makes me happiest and proudest, and I can do it because I’m just working for the freedom.
When you are inventing a job, you have to sell yourself a little harder than people who just apply for jobs that already exist, right? Maybe that’s doing free work to build your name and field of experience. Maybe it’s designing projects you want to do before you're asked to do them. But be discoverable, show up everywhere, be available, be a helper. Show others how you’ve done it. And as you are inventing your own job, it is good to keep working. Do whatever you have to do to make enough to live. Figure out the bare minimum you need per month, do whatever shit you have to do to get that, and then use the rest of your time to invent your job, to do all that free work that you must put out into the world to establish your expertise and credibility. There is no shame, nothing wrong with busting your ass in a job you don't love for a while, for the privilege of having the time for that experience-building and risk-taking.
Also, there are hard truths you may have to examine and accept in the process. If you can’t figure out how to make your skills work for you, maybe you just aren’t built for it. Maybe it’s not for you, maybe that’s just reality. Not all hobbies need to become businesses, and keeping your interests in the realm of “hobby” is not a failure at all. But if you feel like you’re on to something, keep throwing darts at the board—you’ll hit something that sticks. It takes a lot of emotional, physical, and financial energy to build a business from interests you, the things that make you happy. So don't worry if you have spend more focus on the weekends or evenings or whatever else. Entrepreneurs feel very guilty about having side projects, or about needing other work. At first--and still, sometimes--I felt like shit having to do Airbnb to make ends meet after putting all my cash into founding a new startup. Sometimes months go by when I haven't slept in my own bed, save a few nights here and there between guests. There have been weeks when I commuted an hour to sleep at my parents' house, and weeks when I couldn't afford the gas so Alice and I just camped out in my office. It’s hard to not think to yourself, "Wow, I am not successful enough and I have to go back to the trenches. I never thought I'd be here." But that's how it's always gonna be--a cycle of work and passion, passion and work, all in different incarnations as you keep moving forward.
So I believe that your work does not need to be your passion. You do your passion at work. You do it for the love of the machine, not just for the cogs that you are always maintaining. For me, the big picture isn't Hello Holiday. It's my whole life. I do Hello Holiday, I assist on organization boards and with associations, I go to meetings, I write, I seek people who seem to have things to teach me, because all these things have to do with why I get to be free. The conventional world order has blown up because there are so many new ways to work and live. We can work from anywhere, and for seekers, what could be more tempting? At the same time, the overload of resources and inspiration also creates unrealistic pressure to be 100% confident—not to mention successful—in our pursuit of our passions. Don’t let yourself succumb to that pressure!
It's your story, and the more of it you can author yourself, the better. Anything is better than nothing. And anything more than nothing makes you radically different from so many others.