When You’re at a Crossroads, Open Yourself Up to Reinvention
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Everybody loves a comeback story. But being the comeback story? Well, that part’s tricky. After years of craving more control and being maddened by consensus-driven decision-making, I looked my steady paycheck in the eye and said, “Peace out, here goes nothing.” Then I dove headfirst into the world of entrepreneurship. What I lacked in experience I made up for in excitement.
I didn’t know everything, but I was more than ready to learn — and I was committed to my vision. I started up two companies, and that optimism and confidence fueled me for five years. And then I had to close both of my businesses. Humiliated and angry, I couldn’t possibly see how I’d ever move from “I failed” to “I learned.”
Today, I understand that these moments are catalysts for reinvention — a term that’s a little overused and largely misunderstood. There seems to be an expectation that, when misfortune arrives, you just spin around and a new you magically emerges. I don’t know of any cases where transformation has been easy or instant.
Reinvention is a process. It’s learning as you go. It’s forming new habits and behaviors. It’s growing. Sometimes it takes a little push, like losing your business, but you don’t have to hit rock bottom to reinvent yourself. You can start from wherever you are, taking steps toward the career and life you want to cultivate. And how do you know when you’ve achieved these? You don’t — life is continuous reinvention, continuous progress.
Finding Your Catalyst for Reinvention
Reinventing yourself shouldn’t be some desperate maneuver to get yourself out of a jam. When we do things only because we’re forced to, it limits our willingness to think big. When we do things because they make us the people we want to be, the possibilities come into view.
“I feel like I have a job to do, like I constantly have to reinvent myself. The more I up the ante for myself, the better it is in the long run.” – Kevin Hart
Here are five strategies for optimizing your mindset:
1. Sit with your feelings
Nothing could’ve prepared me for the pain of losing my businesses. Transitional periods are rarely comfortable, and changing careers can be emotional, but I had some very serious dashed hopes to deal with. I’d just watched my dream topple to pieces. But as the saying goes, if you’re going through hell, keep going. So I embraced the discomfort.
Your feelings are yours and no one gets to tell you whether you should have them. If you try to push away grief or deny its legitimacy, it will hover around the edges of your mind and infiltrate your thoughts. You must let it in, affirm that it’s there for a reason, and then let it go. Trust me, it will go.
2. Step away for a bit
If you’ve had a setback, you don’t have to give up on your vision, but it helps to take a break. Spend some time on self-care. Paint. Go for a hike. Daydream!
Author Ozan Varol, in his book “Think Like a Rocket Scientist,” emphasizes the importance of unstructured downtime. We don’t give ourselves enough time to play, dream, or simply do nothing, but when we do, it stimulates the brain’s default mode network. “Default mode” doesn’t sound exactly productive, but neuroscientists have found that ideas and clarity emerge when we park our worries and shift our brains into neutral.
While you’re getting your creativity and fitness on, listen to inspiring podcasts. The internet is packed with dialogue from people who’ve been in similar situations or are where you want to be.
3. Keep the internal conversation curious, not contentious
Do you ever listen to the things you tell yourself and think, “Wow, I’m kind of an asshole to myself?” It’s human nature to beat ourselves up after a setback, but if something is too mean to say to others, don’t say it to yourself.
Here’s an exercise I use to reflect on tough situations. Make up a character. I call mine Betty. Give this person a fashion style, a hair color, hobbies, a family; make the character real. Then, cast that person in a role playing you; visualize your situation with this character playing your part. You’re the observer, not the judge or jury.
Let’s say you’ve been laid off. At such a painful moment, it’s easy to start inserting a self-blaming narrative. You replace reality with your heightened insecurity and emotions. It’s self-destructive, but your brain can’t help coming up with explanations where you’re the one at fault.
If you imagine Betty in that scenario, you’ll view it more clearly — realizing that certain situations aren’t personal. Would you say, “Hey Betty, how’d you screw that up?” No! You’d tell her what you can see as the truth: The company had to cut back. You’d probably send Betty a note wishing her well.
If you can view the events in your life as though they were happening to someone else, it’s a little like watching a movie. Aren’t you curious about what’s going to happen next? You’ve learned some lessons. Put them to work and find out where they take you.
“Talk to yourself like you would to someone you love.” – Brené Brown
4. Talk about it
I wasn’t the first entrepreneur who had to shutter operations — not by a long shot. An analysis by CB Insights found that 70% of startups fail, typically around the 20-month mark and with about $1.3 million in total funding. Those are some sad stats, but what a relief it was to find I wasn’t alone.
Whatever you’ve faced, you’d probably be surprised to know how many others have faced it too. You might even find it cathartic to tell your story in an open, vulnerable way. When talking with potential employers or startup partners, don’t be the tough guy who hides mistakes. Businesspeople are no strangers to failure, and they’ll likely empathize with you. They might even share their own experiences. What you think is your downfall could actually be your point of greatest connection.
The research supports this. A study published by Harvard Business School found that a willingness to discuss failure, humanizes you. So stop trying to go it alone. Find people you trust and respect. They’ll see things in you that you can’t see. Inner work is important — but so is reaching out.
5. Focus on the next play
You’ve worked through your feelings, stepped back and recharged, ditched the self-blame, learned. And you’ve asked for help — that’s the toughest part, so kudos. Now, it’s about moving forward.
Duke Blue Devils basketball coach Mike Krzyzewski has a great saying: “Next play.” I often borrow this phrase when I’m talking with my teams. It’s practical, straightforward, judgement-free. Messed up an interview you know you should’ve aced? Next play. Spent the last week basking in praise for a campaign you just launched? Next play. Staying in one place isn’t growth.
Next play is all about restarting quickly. You score some three-pointers and miss some free throws, but you keep playing. And every play is a new opportunity.
Two failed companies and several career pivots have meant numerous trips to the crossroads for me, and each one has shaped my own process of continual reinvention. It’s not a magical shape-shift. It’s a long — sometimes difficult, sometimes joyous, always surprising — road, and every step you take gets you closer to the you that’s possible.