Here’s how you can use baby steps to turn pivoting from an overwhelming giant leap into something manageable.

Step 1: Break Your Dream into Smaller Pieces

No matter how seemingly large, complex, or overwhelming, every pivot can be broken down— divided from larger leaps into smaller steps.

The starting point for the baby-step process is to simply brain-storm the steps—as you see them now—for your pivot. For example, let’s say you want to start a small business making custom furniture. Here are a few obvious things that might jump to mind:

  • Learn about entrepreneurship.
  • Apply for a small-business loan.
  • Buy tools.
  • Set up the garage.
  • Create a website.

Notice anything about these steps? They’re all still big steps. “Learn about entrepreneurship” is a step that can take your whole life. “Set up the garage” might mean holding a garage sale, insulating the garage, reroofing, upgrading the electrical supply, and who knows what else. It’s a huge step, and that means it’s also a huge barrier.

The steps are also maddeningly vague. What does “Buy tools” mean? Does that mean spending $20 or $20,000? What tools?

And how about “Apply for a small-business loan”? What if you can barely afford your current debt? That one is so scary it’s enough to keep you from even making a list, never mind actually doing anything on it.

The key to successful baby-step breakdown is to ensure that (a) you have the smallest possible steps and (b) the steps are specific.

Learn about entrepreneurship? That might mean buying a book on small businesses. Or signing up for a workshop. Or taking an online course. But which book or course or workshop? The real first baby step, then, might really be “Research the top ten best books for first-time small-business owners.” It’s small, and it really can’t get any more specific. As a result, you can actually do it. It’s a ten-minute task that you can do while enjoying a cup of coffee in your favorite chair. It’s not scary. It’s not risky, expensive, or vague. It’s not even hard.

You can repeat this process for every pivot step you can think of.

Your breakdown can be a long list or a more free-flowing mind map. Once you have all the steps, you can begin to identify which ones you think need to happen first. Why go to the bank for a business loan if you don’t know how much money you need for tools? Why look at tools if you don’t know how much space you have in the garage? And why do any of it if it’s your first time starting a business and you’re not sure how the whole idea even works?

Once you begin to break your list of tasks into the smallest possible steps, you’ll be amazed at how many things suddenly seem doable.

*PIVOT POINT: Any part of your pivot can be broken down into easier, smaller, safer steps.

Step 2: Try It On

If you have kids, you might have participated in a bring-your-son/ daughter-to-work day. It’s as simple as it is entertaining: You bring your child to your workplace and let him or her see exactly what it is that Mom or Dad does in a day.

The idea is a great ego stroke for parents, a learning opportunity for kids, and a bonding activity for families. It’s also a remarkably powerful pivot tool, and one that should rise to the very top of your list of baby steps.

“Try it on” is a career-day-for-grown-ups approach to pivoting. The idea is simple: If you have a job, career, business opportunity, or lifestyle that you’ve wanted to try, then try it by spending time with someone who’s already doing it.

It’s that easy. Want to start a restaurant? Open an online store? Become a Buddhist? A vegan? A marathoner? Find someone who’s done it and talk to him or her. Better yet, join that person if you can. If you want to start an online business, spend an afternoon with someone who’s doing it.

The benefits of “trying it on” are enormous:

Fear reduction. Change is daunting. The idea of transitioning from a career you might have had for decades to something you know almost nothing about is intimidating, to say the least, and it raises that pivot killer of never starting. But what if you could get a risk-free taste of what your “pivoted self ” might be in for? You can do so by “trying it on.” If you want to be in real estate, there’s absolutely nothing scary about simply talking to someone who does it.

Real-world insight. Even if you’re not scared by the idea of pivoting, the wisdom you can gain from an afternoon spent in the company of an expert is invaluable.

Opportunity. There’s a wealth of opportunity in the try-it-on approach. I’ve known pivoters who have found business partners, job opportunities, internships, mentors, customers, key suppliers, and investors by doing nothing more than showing a respectful, honest interest in learning more about the lives of others. One minute you’re having coffee, hoping to learn a little something about becoming a real estate agent, the next minute you’ve got an offer to join a brokerage.

If you’re thinking “But I don’t know any vegans/Internet entrepreneurs/real estate agents/etc.,” think again. You probably do. Even if you don’t, someone you know probably does. You’re almost certainly only one degree of separation from someone who’s already doing what you have in mind. All you need to do is ask. If you’re into social media, put it out there: “I’m looking for a writer willing to share a few minutes with me to talk about their work.” The same applies to the offline world—just ask people. Tell five people what it is you’re looking for, and you’re almost guaranteed to find your way to a try-it-on source.

Don’t be fooled by the simplicity of this step. Exposing yourself to a real-life version of what it is you want can be insightful, reassuring, and intoxicatingly exciting.

*PIVOT POINT: “Trying it on” is a low-risk way to test-drive your pivot dream.

Step 3: Get One Done

Whether your passion is to own an art gallery, start a school to teach financial literacy, create an alternative healing retreat, open a creative writing workshop, or start a playhouse for aspiring playwrights, there is one task you can’t avoid: You have to start.

Of course, starting might just be the biggest, scariest baby step of all. Starting feels . . . big. It feels like commitment. Like jumping. It feels like something you might just never get around to. Yet starting is critical. It’s what kick-starts the momentum you so desperately need to pivot. Until you start, you’re an object at rest. And we all know what an object at rest tends to do.

To break that inertia, I use a process I call “get one done.” It’s the act of taking a single, tangible step toward your pivot.

If you want to own your own real estate business, for example, you will need to first obtain your Realtor’s license, and you will need to sell your first house. Yes, you can google “how to become a real estate agent” for months, but eventually something real has to happen. If you really want to become a veterinarian, you will need to start by taking one course and then go on from there. No pivot happens without eventually getting one thing done in the field that you are pursuing.

My brother, a successful New York City attorney, is also an avid collector of “street art.” He became so passionate about collecting that he decided he wanted to be a curator of the kind of work he loved. Being a full-time attorney with a wife and four small children, it wasn’t likely that he could just become a gallery curator overnight. That didn’t stop him, though. He found an artist whose work he thought was very special, and he found a vacant street-level space in SoHo and opened what is referred to as a “pop-up gallery” show- casing the artist and his unique pieces.

That’s a good example of how you “get one done.” My brother could have talked about doing it until he was old and gray and then said, “Ah, it wasn’t that important anyway,” or, even worse, “Ah, I regret never making it happen!” Instead, he took one significant, tangible step. It wasn’t a huge leap, but it was more than enough to create a whole lot of momentum and gain a whole lot of experience.

That step taught my brother that although the the pop-up model was successful, he didn’t want to own a physical gallery. Instead, he wanted to help young artists and raise the profile of the street art genres he loved in other ways. Based on the momentum of his one tangible step, he still practices law, but he now also represents artists in Brooklyn and Manhattan, buying and selling the art he loves and brokering deals for others who love it, too.

*PIVOT POINT: Taking one tangible step toward your dream can kick-start the momentum to making it come true.

Step 4: Repeat

The three steps to baby-stepping—break it down, try it on, and get one done—aren’t rocket science. In fact, they’re obvious. A five- year-old can do them. A toddler uses the same steps to learn to walk.

What makes them so important, and worth describing in detail, is that you can pivot with just these steps. As long as you keep repeating them, your pivot will continue to move forward, and your momentum will grow.

When in doubt, break it down. If you can’t seem to get the next step in your pivot done, it’s probably not broken down far enough. Get more granular. Break it down until the step is small enough that you can take it.

When you’re stuck, try it on again. If you’re not sure what to do next or you feel you’ve lost your momentum, go through the try-it-on phase again. Find someone who’s done it, and get with them.

And just keep getting one done. Eventually one is five, then many, then an entire pivot.

That’s it. With just those three steps you can baby-step your way to freedom.

*PIVOT POINT: When in doubt, return to baby steps.



Comment below and let me know what your biggest take-away from this article is and how you plan to use it in your day to day life!