Seeds of Wisdom: Not Every Hat is Yours to Wear
It’s time celebrate the harvest and begin planning for 2027.
Happy Autumnal Equinox!
This year, I am getting ready to start my strategic planning for 2027 by sorting through all the drawers and cupboards where I have stashed the all my big and small ideas for growing my business with new programs, technology, speaking engagements, podcasts, and another book that I set aside throughout the year.
In the process, I found a huge box of hats. I found hats that I forgot I ever wore that were stuffed into long forgotten dark corners and hidden deep in closets.
As a life-long entrepreneur, I’ve worn a lot of hats. Some were custom made and have become treasured companions, some were borrowed and need to be returned, and far too many never really fit and need to be passed on to people who would enjoy them.
If you have been in business for more than a few years, I bet you have accumulated a sizable box of hats too.
Why Entrepreneurs Wear So Many Hats
There is a lot of buzz these days about how most entrepreneurs are living with ADD or ADHD. The research suggests that ADHD and significant ADHD traits may be considerably more common among entrepreneurs than in the general population.
Whether or not they get an official diagnosis, most business owners can identify with the common descriptors of ADHD like feeling highly distracted, feeling challenged with prioritization, and procrastination.
Many entrepreneurs also tend to lean in to the strengths associate with ADHD, like having surges of high energy and a willingness to take risks, being spontaneous, creative, curious, and adaptable, being able to generate ideas quickly, and possessing the ability to become intensely absorbed in something compelling (aka hyperfocus).
There is something inherently baked into entrepreneurship that lends itself to wearing lots of hat and feeling like there is never enough time to implement all the bit ideas.
You Were Never Meant to Be Good at Everything
Yes, it’s true that every business needs to sell some kind of products or services to customers through various marketing and sales strategies and have systems to track and forecast those sales.
It’s natural to have strengths in marketing OR finance OR operations, but not all three. Without being fully conscious of it, most consultants, coaches, and trainers instinctively create businesses that rely heavily on their natural strengths.
The secret to success in business is not about becoming an expert in everything. It’s about leaning into your Superpowers and compensating for your Bozopowers.
Every business owner has a unique combination of how they tap into their Superpowers. The differences may not be obvious on the surface. Take a peak behind the scenes and you will find one business owner who does all her own accounting and another who hires it out. Some entrepreneurs love to do all the social media or website management and others get help.
But these differences go much deeper than whether you enjoy bookkeeping, social media, or technology.
We each have a natural way of approaching entrepreneurship.
The trouble begins when we assume there is one right way to be an entrepreneur and start collecting hats that were never meant for us in the first place.
Over the years, I have come to recognize distinct Entrepreneur Styles that influence how we lead, make decisions, communicate our message, attract clients, organize our businesses, and grow.
The next time you meet someone selling a very particular kind of hat, make sure it looks as good on you as it does on them.
The goal is to create a business that you love, and that loves you in return.
That is where knowing your Entrepreneur Style becomes powerful.
Your Entrepreneur Style
The day understood my Entrepreneur Style, was the day I was finally free to be true to my own nature as an Entrepreneur.
Knowing your Entrepreneur Style does not mean you become a prisoner of your preferences. Being an entrepreneur requires all of us to flex into less-preferred territory from time to time, whether a task, client, or new opportunity calls for it. Flexing can be useful, and sometimes it is exactly how we learn, stretch, and grow.
The problem comes when flexing becomes the norm. Sustained flexing is draining and often shows up as taking longer to complete tasks, needing more quiet or recovery time, feeling depleted, or losing your sense of humor. When you understand your Entrepreneur Style and know your Superpowers and Bozopowers, you can design your business to reduce unnecessary flexing and create more space for the work that energizes you.
When Superpowers Become Bozopowers
Throughout the past many years of coaching solopreneurs and entrepreneurs of all shapes and sizes, I am reminded again and again that when people don’t honor their types, their businesses, employees, and customers suffer.
• Wildly inspired INVENTIVE DESIGNERS who try to manage every detail of their businesses may inhibit the natural growth cycle of a maturing business and keep it in an artificially prolonged start-up phase.
• Structure-loving STABILIZING ADMINISTRATORS who build too many systems before they are needed may suffocate their sprouting businesses in the fast-paced start-up phase.
• Perfection-seeking HEALING ADVOCATES, who spend too much energy trying to get consensus, may discourage people from speaking up in meetings for fear that another round of discussion will ensue, and projects will languish.
• Harmony-at-any-cost PROTECTING CARETAKERS may spend too much time “checking-in” to make sure everyone is “Okay” that they don’t address the blaring deficits in technology.
• Do-it-on-the-fly CRUSADING MOTIVATORS may only send invoices seasonally, leaving their businesses starving for cash.
• Strategic-planning MOBILIZING STRATEGISTS who create intricately designed systems to support their projects may turn off customers when they drop the niceties of chit-chat at the start of meetings.
Design Your Business to Fit You
An ideal balance to strive toward would be to use your Superpowers about 60% of the time in your business. Being in business is hard enough without forcing yourself to operate well outside your preferences for most of the day.
As a VISIONARY MENTOR, I am naturally inclined to coach, counsel, and consult with people about what they want to be doing with their lives and help them get on with doing it. I am not naturally inclined to maintain my database, organize my financials, or file my taxes.
I used to think I had to do everything in my business. I convinced myself I couldn’t afford help and berated myself for struggling with tasks that seemed like they should be simple. Eventually, I learned to create a supportive environment around my Bozopowers. Two key parts of that environment are my Accountant and my Assistant. Their support frees me to spend more of my time doing the work that draws on my Superpowers.
Taking Entrepreneur Styles to Oxford
This understanding of Entrepreneur Styles is fundamental to the support I provide to my clients. In 2027, I will be publishing my next book, Entrepreneur Styles to share it more broadly.
On September 25, I will be in Oxford, England, presenting Entrepreneur Styles at the British Association for Psychological Type conference. I am excited to bring this model to my peers in psychological type and to explore how our natural preferences shape not only who we are, but how we build, lead, and grow businesses.
Because there is no single right way to be an entrepreneur.
There is your way.
Which Hats Are Really Yours?
As you begin looking toward 2027, take another look at the hats you have accumulated. Which ones fit naturally? Which ones are useful to wear occasionally? And which ones have you been forcing yourself to wear simply because someone told you that a “real” business owner should?
Keep the hats that allow you to do your best work.
Get help with the ones that don’t.
And let go of the ones that were never yours to begin with.
That is how you begin creating a business that you love, and that loves you in return.
If you want to learn your Entrepreneur Style, let’s talk soon
