Episode 27: How to make a second (or third) career pivot more successfully with Jess Glazer

Welcome to The Career Clarity Show, where we help you find a lucrative, soulful, and joyful career path for you! 

Have you made a career pivot before, but feel like you didn’t get it quite right? Does the thought of pivoting *again* to try to be happier make you break out in a cold sweat?

Meet Jess Glazer. Jess knows a thing or two about that feeling — she’s been through her fair share of pivots.

A quick summary of the twists and turns in Jess’ path: she started her career pursuing her doctor of physical therapy, with a fallback undergrad degree in teaching. Then, she accidentally started a fashion and accessory business, so she got a degree from the Fashion Institute of Technology in New York City. After graduating, Jess felt pressure to pick something safe and reliable, and ended up going back to teaching. (The FOMO of seeing everyone else around her established in their careers and starting to settle down with families was real.).

For anyone who’s made that first courageous pivot…but don’t feel like you got it quite “right” the first time, the prospect of making another pivot might feel scary as heck.

When you commit to one direction but learn something that makes you wanna change course again, it can feel uncomfortable. Frustrating. Disappointing. Hopeless.

And, change feels risky.

Because we usually (excitedly) told our friends all about our new career and get some social approval — you know, because you look like you’ve got your shit together, have a solid plan, and seem to have it “all figured out” on paper. So when you have an “uh-oh” moment and decide to change course, it can feel like you’re jeopardizing that social support. And that’s ON TOP OF taking a risk on a new direction that *might* not be perfectly right (again). Yikes, right?

For Jess, teaching elementary school phys ed was wonderful, but she knew it wasn’t a plan that would feel wonderful forever. After so many pivots in the beginning of her career, it would have been easy for her to say, “Suck it up, Jess. You’ve gotta ignore those feelings, girl. The grass isn’t always greener, and you like your work well enough.”

The problem with doing that? Relying on these kinds of defense mechanisms (especially minimizing or rationalizing, as in: “Oh, it’s no big deal” or “It wasn’t a good fit anyway”) is a surefire way to talk ourselves out of our truth and cause us to massively question ourselves. It’s also an excellent way to create painful judgments and stories about what our career choices mean about us as people: that we’re failures, that we’re behind, that everyone else is successful and we will never be.

You need to know there’s a critical separation between defining yourself as “the person who pivoted and failed” and “the person who’s continually growing.” This distinction (beautifully articulated in Carol Dweck’s mindset research) is the difference between having a “fixed” mindset and a “growth” mindset.

(Click here to learn more about these two differences in mindset.)

Because Jess chose a mindset that trusted her intuition, and was confident in her sense of direction and ability to constantly evolve, she knew it was time to make a shift. Feeling like you can’t breathe (and exhale) like you want to will do that to you.

She used each experience like a trampoline to effortlessly bounce into the next great-fit idea. She leaned into her interests in fitness and coaching and did some personal training on the side when she wasn’t teaching. This helped her start exploring building a business that could give her freedom (beyond those coveted summers “off”).

A lot of people stress about finding time to play with side hustle ideas (and that’s totally normal), but Jess has some great suggestions that helped her spring into each of her successful, profitable businesses, from fashion accessories to personal training to fitness vacations to business coaching for entrepreneurs.

(1) Give yourself permission to do things you love. If you want your future side hustle to be successful, it needs to be rooted in things you actually like. (In the Career Clarity methodology, we call this being aligned with your Strengths pillar.) If you don’t root your side biz ideas in your enjoyable, energizing Strengths, you’ll basically be forcing yourself to do work you hate…while also trying to learn all the new skills you’ll need to be a successful entrepreneur. It’s not a pleasant road. *shudders* So, yes, absolutely use the things you enjoy to build a possible new income stream, but let it be playful and not pressurized at first. Even just investing one hour a week into something you love and increasing your mastery at it will pay happiness and momentum dividends.

(2) Notice what people ask you for help with. If you’d love to start a side hustle but have no idea what people would pay you for, good news: you don’t have to guess. You can ask. (Yep, it can be that simple.) We often put pressure on ourselves to already divinely know the perfect business idea for ourselves, but sometimes the most obvious (and awesome) ideas are ones that other people can see better. Have people in your life asked for your strategic counsel on specific types of projects? Do people compliment you on your baking, your crocheting, or your singing voice? All viable side hustles! By listening to the voices around you, you’ll know there’s market demand for your help. Here’s a perfect example for you: I got into career coaching because I had a funny habit of going to brunch with girlfriends, telling them to bring their resume, and dropping TONS of knowledge on them between bites of eggs benedict.

(3) Try the smallest possible prototype. Jess started her profitable accessory business by creating a few bag samples and taking orders for more, which resulted in more than $6,000 in sales…in a single day. She had low overhead, low upfront time, and a low initial energy investment to see if her proof of concept intersected with the market demand. She created the minimum viable product, and use enthusiasm about it to help her decide how to build more (and keep herself from going into huge debt. (Learn from the stories of other entrepreneurs like Nicole Iacovoni’s, who had to dig back out of $80,000 of credit card debt to make her business profitable.) Even Google does tiny prototypes. When they were playing with the idea of creating Google Glasses, they created a mock-up with a cheap pair of plastic glasses to see how it could work before they ever manufactured a fancy pair. Proof you don’t have to go all in right away!

(4) Let yourself nerd out. Jess attributes her exponential growth to learning everything she could and avoiding making other people’s mistakes by hiring a coach. She became totally obsessed with getting better and better, which led her to pivot her business model from personal training to fitness vacations to teaching other side hustlers how to scale and leverage their businesses. Thanks to nerding out and focusing on learning, she became an incredibly strategic businesswoman in the 2 to 3 years since she quit teaching and has built a multi-6-figure business. If you’ve been curious about downloading that new podcast, getting a fun new Kindle book from the library, or hiring a coach, here’s your permission slip to dive in and geek out. You never know what you’ll learn and where that’ll take you.

(5) Don’t discount the value of your past steps. The two threads that have always run through Jess’ professional moves are fitness and teaching — and, even though she no longer does personal training or FitTrips, she still uses the principles and foundations she learned in her past moves to structure her future ideas. Everyone takes steps that open up new possibilities. The important part isn’t knowing where those steps are going to land but that you start taking them. As the intuitive philosopher Rumi says: “As you start to walk on the way, the way appears.”

Jess echoes the same principal: “You have to understand there are stepping stones to get there, and you never actually know where those stones are going to take you. You couldn’t have even told me three years ago I’d be a business coach! That wouldn’t have made sense!”

These five steps alone won’t get you to multi-six-figures like Jess — as she shares on The Career Clarity Show, she pairs these principles with a lot of hustle and effort — but they will start building your momentum.

Jess says: “If you want something, you will figure it out.”

And, if the worst thing that happens is you quit your side hustle and just go back to what you were already doing, you made a choice to take a chance and take a tiny baby step forward. You don’t have to keep living your worst-case scenario.

SHOW NOTES:

• Read more about Jess Glazer
• Follow @Jess.Glazer on Instagram
• Career Clarity LIVE in Englewood, Colorado
• Roadmap to a Fulfilling Career eBook

Subscribe to The Career Clarity Show on Apple Podcasts, Stitcher, Spotify, and Google Play.

And, follow The Career Clarity Show on Facebook and Instagram — and sign up below to receive emails when new episodes come out!