Taking the Leap and Building Your Wings on the Way Down

Sometimes you just have to take the leap and build your wings on the way down.

That’s a quote that is attributed to author Kobi Yamada, but I may have said it more than any other human on the planet. It means SO much to me, and it has been the phrase I held on to so tightly while I transitioned through different life stages, career paths and more.

Another version of this, by the way, is the John Burroughs quote: “leap and the net will appear.”

What do they both mean? Here’s my interpretation:

When you take a chance, or pursue something new, or put yourself into a position where you MIGHT succeed, but you also COULD fail…

…you can’t wait until everything is perfect. It will never get there. And I’m a near-perfectionist, Enneagram 1, Type A, project managing systems specialist, y’all!

What you CAN do is plan just enough to get you to the edge. By the way, I fully realize that in some instances, the best outcomes actually started with no plan at all.

How many of you started your business because you’d been laid off from a job, or had burned out in your role? How many of you found yourself wildly off course from your plan, because of a divorce or other life event? Are you a parent? That sure changes your perspective – not to mention your free time and ability to think (I say this as someone whose mom brain sometimes has me unable to complete even basic tasks).

If you didn’t walk up to the cliff and leap – because you were thrown off the edge without warning – the opportunity to reframe your mindset and your goals is the same.

So, let’s talk about it in more actionable detail.

Let’s say you want to start your own business. And many of you listening ARE considering this. I know because every time I run a poll on LinkedIn or Instagram…any time I’m at wine night with the girls or a coffee date with friends…each time I listen to conversations at the nail salon or in Target, I learn that almost everyone has an idea – but almost all of those people are too afraid to try.

To start a business, what do you need? These days – not much!

At bare minimum, you can launch your first business with:

  • A basic product or service
  • A simple way to take money (PayPal, Venmo, CashApp, Stripe are ALL easy to set up in less than an hour – you can worry about the more robust systems later!)
  • A one-page website or even a social media platform (I am still a WordPress holdout, but platforms like Carrd – that’s with two “r”s, SquareSpace, and Showit are all great options, or if you have an email service provider like ConvertKit or MailChimp, you can even create SUPER simple landing pages and products right there!)

And you’re off! Today, I have a very sophisticated tech stack. It includes a network of websites, email service providers, e-commerce and payment processors, automated proposals, invoicing and more.

AND, I have a team! My fractional CMO and CRO agency services come with a graphic designer, a videographer, a copywriter, a public relations and media outreach specialist and more…PLUS, I have a dedicated finance team to help me spend more time working on the business than in the business.

When I started, though? None of that. I had a free gmail address, proposals that I wrote up in Google Docs, invoices that I sent through PayPal and a lot of non-scaleable but revenue-generating systems.

Taking the leap for a new business owner might mean coming up with the idea, testing it with a small group of friends and family – thereby lowering the overall investment AND risk – and once you have a few sales and testimonials, you can start reinvesting in the next things…rinsing and repeating until you have a more profitable, scalable business.

Maybe taking the leap in that case means working on the business at night and on weekends, proving the business’ viability and then later leaving your full-time job.

Here’s another scenario: maybe you’re perfectly happy in your job and career, but you want to move. That was me for a while, too!

I grew up in New England and went to college in Syracuse, New York. I’ve DONE my time in the winter weather, friends.

So, my then-boyfriend, now-husband, and I decided to move to the beach in Florida. I could not WAIT to spend every day with my toes in the sand.

Joke’s on me…I took a job in Orlando, not fully realizing that it was in the middle of the peninsula, a full hour away from the nearest beach. I spent about as much time with my toes in the sand as I did when I lived in Syracuse and flew to South Beach for spring break a few years in a row.

Fast-forward 10 years, and we had the opportunity to move to St. Petersburg, two hours outside of Orlando and ACTUALLY at the beach.

Now, though, I wasn’t traveling with my boyfriend, an old beater car, no kids, and little risk.

I owned a home with my husband. We had a 2-year-old. I was newly pregnant. We had two dogs! And leaving Orlando meant leaving my full-time job, too.

I desperately wanted to move. I knew this was right for me and for my family. But I was scared.

So…we said yes to moving. And said goodbye to Orlando. And the house. And the job. And with no firm plans – no place to live, no job lined up for me, no midwife for my pregnancy – we took the leap.

And over the next few weeks and months, I built those wings. I found us a condo that would accommodate our two big dogs. I hired a property manager for our Orlando home and we became landlords. I told the clients I’d been working with at night and on weekends that I was going into business for myself, officially. And those wings grew and grew.

I am NOT a risk-taker. Not really. But I’m also unwilling to let life pass me by. 

I have a tattoo on my arm that says “I’m on it” and it’s a quote from my dear friend Wendy Chioji. Wendy battled and beat breast cancer and later battled and ultimately died from another form of cancer – thymic carcinoma. She lived YEARS beyond her doctors’ best hopes, and during that time, she traveled the world, competed in triathlons and running events, raised a TON of money for cancer research, participated in clinical trials. She LIVED BIG and loved hard.

Wendy was 57 years old when she died and before her death, she shared some thoughts with my then-boss, Marc Middleton, the founder of a television program I produced called Growing Bolder.

In a series of videos, Wendy said “I go things and do places because none of us is guaranteed tomorrow. My mantra is ‘say yes.’ I would love to be able to count on 20 more years…I’m not going to have that, I know that.”

She went on to say that she had no regrets, particularly in the 5 years AFTER her diagnosis, when she frequently said yes.

And back to my tattoo? She once said “I have the best life. I’m so blessed. I’m so lucky. No matter what happens, I have the greatest life. Sometimes it’s just to make sure you appreciate the good stuff, that the bad stuff comes. I get it! I’m on it!”

And I hold that so close to my heart and my soul.

I hope you will take the leap. Your net is waiting. You are capable of building your wings. And no matter what, it’s all about ACTION. And the pursuit of joy. Of happiness. Of fulfillment.

I believe in you.