How to Find Your Why
And succeed against all odds
After I sold my social media agency in 2021, people wanted to know how I did it. They wanted to replicate my method to sell theirs. They wanted to find out the shortcuts and avoid the hard way and the long way. Who can blame them?
Success of the most fulfilling kind comes from doing cool stuff and teaching other people how to do that same cool stuff.
Missing a north star on which to base my next venture, I started teaching the lessons from the last in the hope of finding it.
Between traveling, training, and writing Ten Year Career, I doubled down on the topic of agency exits. I put everything I’d learned into a comprehensive course. I took on some async coaching clients, communicating via voice notes to help agency owners systemize and get acquired.
I talked about creating a sale-ready business on a handful of podcasts, shared my story and booked one-off consulting calls with founders ready for a new challenge.
One of these founders had run her agency for over thirty years. Her energy was infectious, and she was straight-talking, super successful and incredibly inspiring. She radiated charisma even through the screen on our Zoom call, with big hand gestures and a beautiful way of telling stories and explaining why she was ready to sell.
To thank me for our session, where we covered adapting the business to run without her, she sent me a personality test that she used with her team of 200 employees. It was, she explained, better than Myers-Briggs and the others out there. With Insights Discovery, there were no bad results. It was fun. The 20-page reports inspired people to do their best work.
I took the test, and the report was emailed over. Within pages of explanations on my working style, strengths, weaknesses and communication preferences were insights that were absolutely bang on.
Beyond a novel report, that test highlighted something I hadn’t realized until now: how I was motivated. My why. That single-line, pivotal nugget, never before put into words:
“The possibility of succeeding against the odds.”
Finding your why
We are each motivated by different things. One person loves metaphorically killing competitors, another climbs a leaderboard, and another proves someone wrong. Someone else wants to make someone proud.
Looking back at everything I’ve ever done, the things that meant the most were instances where the odds were stacked against me, where I succeeded despite the hand I held.
Selling my agency had felt special because, despite agency earnouts being an average of 3–5 years, my handover took two weeks. People told me it wasn’t possible to avoid an earnout, but I did it.
The agency’s name contained my initials, which countless people said made it unsaleable.
After a week in March 2020, when we lost 25% of our clients in one week, the team rallied to find new clients and grow to a new level when the odds were not stacked in our favor.
I love being told that something isn’t possible. I love hearing why something won’t work and then making it happen. I love being that one in a million who finds a way through when others give up.
That is my why.
How do you find your why?
Reverse engineer the process.
Think of every time you’ve been disproportionately proud of something you’ve achieved, even the small things. Make a list and find the pattern. What kept you going when it got tough? What’s the real reason the victory feels so good? Take personality tests and see if they can put it into words better than you. Ask ChatGPT to probe you until it can work it out.
Find out how you are uniquely wired based on your previous work.
Aligning your actions
The personality test insights didn’t stop with one sentence. Looking back, I realized that every aspect of my work was connected to this simple concept. Not only was I motivated by the possibility of succeeding against all odds, but I loved helping others do the same.
In my world, satisfaction comes from handing people ace cards:
- I started a digital agency in 2011 to help companies make the most of this new-fangled thing called social media.
- I co-wrote a series of children’s storybooks in 2013 and a book on raising entrepreneurial kids in 2018 to give entrepreneurial role models to people without any.
- Creating resources to help agency owners exit would help them shortcut their way to an acquisition, using what I’d learned to figure it out from scratch.
Succeeding against the odds. Leveling the playing field. Handing people ace cards. That’s my jam.
It was all making sense.
Find your why and do the same. Figure out how it’s been dictating your work and sense of purpose all this time. Build more of a picture as to why you do what you do. Start to understand what makes you tick. Test the theory, ask your partner and friends, and geek out on what gets you out of bed and revved up to progress your mission.
Keep pulling on threads until you find your why.
Project it forward
The past brought us here with lessons and experience. Building on the past in the future means applying the lessons and using them. Not being content to review and reflect then close a chapter, but channeling insights into the success of a different kind.
As soon as I had defined my concept, it was simple. The odds have to be stacked against me to get excited about any project. To spark motivation and passion that carries me through the lows, the surprises, and those “all is lost” moments, there has to be a high chance of failure, big risks for big rewards, and countless reasons why it won’t work.
Low odds? Slim chances? Bring them on. It’s exciting to hear about why my company might not succeed. It’s fun surprising someone who had underestimated you. I like having nothing and everything to prove at the same time.
My method might do nothing for you, and that’s fine. We are each motivated differently. Take what made your past successes and apply the logic. For example:
- A friend motivated by climbing a leaderboard checks his website traffic against his competitors’ every single day.
- Another committed to self-development logs metrics of personal wins across a whole host of areas.
- Someone who wants to prove someone wrong keeps a written mantra on their desk to ensure they stay on track.
Visual cues, constant reminders, and everyday nudges so you never forget or veer off course. Turn your personality insights into a method that secures your future wins.
The flipside
For each of your strengths, there is an accompanying weakness. The best version of you plays to your strengths. The worst version lets your weaknesses creep in to rule the show.
Your why is exactly the same:
- Someone motivated by earning as much money as possible can become oblivious to anything else. Obsessed with cash, they do deals even when they don’t make sense.
- An entrepreneur who wants to make their parents proud loses their own identity in the pursuit of acceptance by someone else’s metrics, eventually feeling lost.
- A business owner who loves competing struggles to pick their battles or opt out of contests. Their focus wanes as they get sucked into games that don’t matter.
Every action has a reaction. Every solution has side effects.
In figuring out my why and how it played out in practice, I realized its accompanying saboteur: I don’t play my ace cards.
In valuing the practice of succeeding against the odds, I was subconsciously stacking the odds against me. I was trying to prove I could do it the hard way. I was seeking approval from somewhere other than within. I was playing down my strengths, glossing over those things that would make all the difference — becoming a bottleneck to my own capability by artificially making things difficult.
This saboteur was manifesting in inefficient practices that were holding me back, and it made no logical sense. Instead of paying professional video editors, I was editing my courses myself. After starting Coachvox AI, this continued. I relied on our developers to make roadmap decisions instead of trusting that I knew what our creators wanted. Rather than using my network when raising investment, I researched funds on Google like a newbie. I dabbled with marketing channels that didn’t play to my strengths instead of doubling down on those that did.
I had built a career by handing ace cards to other people, but I wasn’t using my own.
Uncover the clues
Your proudest moments hold clues as to why you do what you do. Those reasons for leaping out of bed in the morning will be the same in the future as they were in the past, but most people don’t bother to find them out.
Instead, they flit around, copying other people’s measures of success, chasing the same possessions or lifestyle as those around them, without questioning what they want. Without knowing their why.
Find your why based on past success. Expand the concept to find patterns in your work. Project it forward to create your future victories. Avoid the accompanying weakness to your unique strengths.
It starts with a simple personality test. It ends with knowing exactly where to go from here.
Whatever you do, whyever you do it, may you maximize the hand you were dealt, play every ace card, and have even the tallest odds stacked in your favor.
