Well, not always. Sure, everyone has heard the stories about women who ditched their safe-but-snoozy desk jobs in order to follow a dream, emerging on the other side happier and healthier than ever before. And while those examples are awesome, it’s much more rare to hear about what happens in the middle—the uncertain period when a passion project is just starting to take flight and things are definitely not all unicorns and moonbeams.
One gal who knows that better than anyone is Amy Woodside, the New York City-based founder of women’s empowerment network OKReal. Not only has her own career path had lots of twists and turns—including stints in advertising, branding, and painting—but her current gig revolves around chatting with some of the coolest creative entrepreneurs and CEOs about how they’ve cultivated success and happiness in their own lives.
Her biggest takeaway: Turning a passion into a paycheck is totally worth it in the end, but it’s way harder than you think it’ll be. “OKReal is about untangling the truth behind the idea of ‘doing what you love,’” explains Woodside, who launched the company as an online magazine in 2014. “You can say your mantras and drink your green juice and meditate, which might help, but it requires more grit than dreaming.”
To that end, OKReal has evolved to encompass live events that help women navigate that tricky territory together, from mentorship circles to workshops and lectures (Next up is a conversation on brand-building with LNA founder Lauren Alexander, taking place in Los Angeles on August 25). “The whole premise of OKReal is learning from others’ mistakes to see yourself more clearly, and let that guide you down your own path,” notes Woodside.
Thankfully, she says, the process of cultivating a dream is a whole lot smoother once you know exactly what to expect—and how to get past the inevitable rough patches that, let’s face it, you are going to encounter.
Here are the eight toughest things that happen when you embark upon a big passion project—plus tips on how to overcome those obstacles.
1. You will be scared a lot of the time
According to Woodside, one of the biggest challenges that comes with making a major career shift is simply getting out of your own way. “We have so many excuses that we use to talk ourselves out of things,” she says. “Even with OKReal, I waited around for a really long time for clarity until I pressed ‘go.’ It got to the point where I just had to do it, even though I didn’t feel totally sure about it.”
Her mantra for busting through that fear: “If it doesn’t work out, I’ll try something else.” That’s because, as Woodside explains, “I’ve always treated life as an experiment. My wonky career trajectory shows that I’m somebody who is really determined to figure out who she’s actually meant to be, and who does whatever it takes to reach that understanding.” Approaching a project with that mindset takes a lot of the pressure off—and if it fails, at least you’ve learned something about yourself along the way.
2. You’ll need to majorly streamline your budget
No matter what it is you want to do, whether it’s taking a year off to travel the world or starting a new career as a yoga instructor, it’s important to be smart about financial planning. While that seems like a no-brainer, says Woodside, “you’ll definitely need more money than you think you will—people really underestimate that. You have to be resourceful.”
Whether that means collecting coupons for your groceries or taking on a roommate to help you cover the rent, Woodside insists that creativity is key. She also cautions that quitting your job without anything to fall back on is a really bad idea, and recommends keeping a steady gig at least part-time to help fund your passion project in the early stages.
3. You’ll have to give up things you love
Money’s not the only thing that’ll be tight when you first decide to “do what you love”—you’ll also find that energy and time will be in short supply too. “Nobody tells you about all the sacrifices,” says Woodside. “You’re exhausted all the time, you have to give up seeing friends, having free time on the weekends…. I work every day.”
Even so, it’s important to remember that you are responsible for how you spend your time, and carving out space for things outside of your dream is crucial. “You will make time for what you choose to make time for, and how you divvy that up is totally personal,” she explains. “For me, that means that I work out in the morning—that’s really, really important to me. I might have to sacrifice sleep, but I always make time for it.” (Not that we would necessarily recommend pushing zzz’s down your priority list—they’re really important.)
4. You will fail again and again—and it will suck
What would you do if you knew you wouldn’t fail? It’s a quote you see in self-help books and inspirational Instagram memes, but according to Woodside it would be a lot more realistic if it actually read: What would you do if you knew you would fail? “There’s every chance that things will go wrong, and failing’s really hard,” she says. And it’s not always the life-altering, catastrophic failures that are the worst, she adds. “The little failures hurt just as much, like someone being mean on social media.”
So how do you get through all of those little disappointments? Just keep going, advises Woodside. “The only way hard stuff becomes less hard is by continuing to show up,” she says. “Something that might have really stressed me out two years ago might not be as stressful now. Just making the choice to get up when you don’t feel like it is really powerful.”
Another one of her favorite tricks: Picture someone you admire and channel how they would handle a situation you’re in. “Sometimes you do have to fake it a bit in order to become more resilient,” Woodside notes.
5. You’ll have to take responsibility for everything that happens—good and bad
When things go wrong, your first instinct will often be to blame someone else. But if you do that, says Woodside, you miss out on an opportunity to grow.
She experienced this firsthand when she received the first unfavorable survey review for one of her events. “I had a really defensive and emotionally charged reaction at first,” she says. “Taking responsibility in that situation was me saying, ‘I did the very best that I could, but is there something that I can learn from this?’ It was about being open and listening to what that person had to say.”
6. You will feel lonely
Even if you’re surrounded by people who love and support you, says Woodside, they might not fully get what you’re doing—and that can be really frustrating. “At the end of the day, you can only rely on yourself,” she says. “You have to believe so strongly in whatever you’re doing that it’s absurd.”
It helps to connect with people who are following similar paths to you, but Woodside cautions against disconnecting from everyone else as you pursue you goal. “Staying grounded is really important to me—I speak with my mom all the time and go home to New Zealand twice a year,” she says. “It helps me see that building my career is great, but it’s not everything.”
7. You’ll have to give up control
For whatever reason, your dream might not end up looking like you thought it would—and it’s important to be okay with that, says Woodside. “We have these truths inside us, and our responsibility is to nurture that truth and help define it. But how it turns out is not up to us,” she explains.
If you’re someone who likes to be in control, that might be hard to hear, but Woodside insists that going with the flow is actually very freeing. “That drive you have is going to take its own shape and form, and your job is just to push it out into the world and be your own biggest cheerleader,” she says. “But you have to do it without controlling it—that’s a really challenging thing to do.”
8. You’ll finally understand what fulfillment really means
Despite all of the inevitable setbacks, says Woodside, taking steps to follow a long-held dream is 100 percent worth it. Even if your big project ends up being a flop, you’ll have learned some really valuable things about what makes you tick, which can go on to enrich every area of your life.
“That’s essentially what fulfillment is—having a really accurate understanding of what you need, as a human being,” she says. “It’s not necessarily a fleeting sense of happiness…it’s more a sense of peace.” And isn’t that worth a few long nights and early mornings in the end?
For more advice on what to do when things go wrong, check out what Misty Copeland has to say about handling criticism, how the Levo co-founder deals with tricky situations in the office, and why this journalist is serious about ending competition among working women.
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