Several years ago, I unexpectedly lost my job as a full-time magazine editor in Dallas. I knew I would be moving to Chicago in six months, so I was stuck in a difficult position. It was too short of a time frame for me to find a new job in Dallas and too early to begin searching for jobs in Chicago.
I was 28 years old. I’d always envisioned following my dream of one day becoming a full-time freelance writer, but I pictured doing it at 35 or even 40 years old, once I had more solid financial footing and a larger network of contacts.
Despite the stomach-twisting, heart-racing fear I felt at diving into this dream before I was ready, it was my best, most practical option at the time. My husband and friends encouraged me, and I figured the absolute worst thing that could happen would be failing after six months and then finding a full-time job in Chicago.
Nearly two years later, I’m still freelancing full-time. Not only am I significantly happier thanks to a flexible schedule and the freedom to take on the projects I want, but I’m making more than double what I did as a salaried editor.
When it comes to big dreams, goals and aspirations, many of us plan out every last detail so that we feel primed for success. But this excessive planning is a way of shielding ourselves from failure and ultimately preventing us from ever taking action. No matter how much planning you do, you’ll never feel 100% ready to take a leap of faith into the unknown.
If my story isn’t enough to sway you to finally pursue your dream, take it from these seasoned entrepreneurs who dived in before they felt ready:
Vivian Chan, co-founder of East Meets Dress
When Jennifer Qiao got married, she struggled to find a modern version of a cheongsam, a traditional Chinese wedding dress, and an idea was born. Neither she nor Vivian Chan, her co-founder, had experience in fashion or entrepreneurship. They didn’t even know if there was a market for their product in the U.S.
One night, the co-founders created a free landing page to test out their idea and discovered there was some interest. The duo created a Shopify website with one dress design over the weekend. After one month, they got their first customer.
“Even though we weren’t very confident that we would be able to make this a reality, we decided to just start small and test out our idea quickly. We never truly felt ready to start a business, let alone make custom wedding dresses,” said Chan. “However, through a lot of hard work, hustle and trial and error, we’ve been able to grow our team and company to a six-figure annual recurring revenue and help hundreds of brides across the world celebrate their heritage in style.”
Nick Gray, founder of Museum Hack
In 2013, Nick Gray went on a date at the Metropolitan Museum of Art in New York City. He instantly fell in love with the spot and began hosting renegade tours of the museum with his friends.
Gray continued working his day job selling electrical equipment for planes and hosted museum tours on the weekend. Word about his tours spread, and a local blog covered them. Over 1,000 people emailed Gray wanting to join his tours. A year later, Gray officially quit his day job and dived in full-time. Museum Hack now hosts over 30 weekly public tours, and Gray recently sold his company for seven figures.
“When I started leading tours of the Met for my friends, I didn’t know it would become a business… But we had momentum—friends of friends kept coming on tour, and then people started finding our website and we started to create a movement,” said Gray.
Jamie Lackey, founder and CEO of Helping Mamas
Five years ago, Jamie Lackey, who had been a social worker for almost two decades, was struggling to decide whether to continue working or stay home with her two kids. Then it dawned on her: The moms she worked with in her role as a social worker didn’t have this choice. They often worked multiple jobs, reused disposable diapers and struggled to put food on the table.
Lackey founded Helping Mamas out of her garage and her friend’s basement. What began as a small project collecting baby items for children, from newborns through age 12, has grown into a nonprofit that has served over 50,000 children and donated over one million items to low-income women and children in Georgia.
“I never take risks. I went into this with a lot of fear. But I heard someone say once that you might only get one good idea, one really big idea, and you have to act on it because it may never happen again,” said Lackey. “And that is what happened. I took a leap of faith, faced my fears and jumped. The time was right. Even if I wasn’t ready, the situation was ready.”
Still not ready to dive in? The following are all tips and tricks for starting before you’re ready:
- Do the 10-year test. This is one of personal development powerhouse Marie Forleo’s tried-and-true strategies. Ask yourself: Will I regret not doing this in 10 years? If the answer is yes, it’s time to start.
- Be on the lookout for overplanning. I felt like I wasn’t ready to start my own business because I hadn’t planned everything out. How would I find new assignments? How would I bill clients? When would I pay my taxes? I thought I had to have every last angle figured out before I could pursue anything.
I started with two clients and no clue about the business side of being self-employed. Now, two years later, I often have more work than I can manage and ample knowledge about the financial side of running a business. It’s important to have the basics of your plan figured out, but try to notice if overplanning is getting in the way of taking action.
- Ignore the voice in your head. Doubting yourself? That’s totally normal. The key is being able to ignore this voice instead of succumbing to it.
“You must disobey the voice in your head that says, I’m not ready yet,” Forleo writes in her book Everything is Figureoutable. “That voice—the one that’s constantly telling you how not ready you are, how much you don’t feel like doing this or that, how incapable and incompetent and not good enough you are—that voice is not you and it’s not true.”
- Take a small step. There needs to be a delicate balance between starting something you care about and being practical—you probably shouldn’t quit your full-time job just because you have a great idea. Instead of fully jumping into something brand new, consider taking small steps. Attempt to start this new endeavor on the side while still maintaining your full-time job. Then, if it gets big enough, you can quit your day job.
This article was published in October 2019 and has been updated. Photo by @wcywendy77/Twenty20
Jamie Friedlander is a freelance writer based in Chicago and the former features editor of SUCCESS magazine. Her work has been published in The Cut, VICE, Inc., The Chicago Tribune and Business Insider, among other publications. When she's not writing, she can usually be found drinking matcha tea into excess, traveling somewhere new with her husband or surfing Etsy late into the night.