5 Lessons I’ve Learned During My Entrepreneurship Journey

Just over two years ago, November 2018, I left the safety and security of my corporate role to pursue Influence PEOPLE full time. I’m amazed at how quickly those years have passed! 

I’ve reflected on the transition quite a bit lately and thought I’d share a handful of lessons I’ve learned. If you’re considering a similar move I hope sharing some of my experience helps you. 

1. Start Planning

I’d been in corporate America 30+ years, ever since graduating college. I started Influence PEOPLE in 2008 because it’s what I knew I would eventually do with my career. 

I’m thankful I planned ahead! For example; I had a website, started my first book, had been blogging for a decade, and built my social media presence all by the time I stepped out on my own. It was overwhelming enough to make that transition so I cannot imagine juggling all of that on day one. 

Takeaway. There’s a proverb that says, “Plant your fields then build your house.” That’s good advice if you want to step out on your own. Start sowing seeds into activities that will pay dividends over the long haul. For example, you can build your social media presence, begin blogging, start a podcast or look to get on podcasts, get going on your website, and many other “infrastructure” activities. The first steps are the hardest but they get easier once you get in a groove.

2. Be Courageous

I’ll be honest, it can be scary stepping out on your own. I remember laying in bed after telling the CEO that I would be leaving. That night my exact thought was, “Have I just f–ed my family?” Thoughts about the cost of healthcare and other unknowns flooded my mind as I tried to sleep. I still wake up periodically when certain thoughts hit and it’s no use trying to get back to sleep.

I think no matter how confident someone may appear, it’s natural to have doubts. I take comfort in this Bible passage, “I do believe. Help my unbelief!” No matter how much confidence, faith, or belief you may have, you can always have more. Courage isn’t the absence of fear or doubt; it’s the willingness to do what’s called for in spite of how you may feel.

Takeaway. Be truthful with yourself and others about how you’re feeling. But, don’t how you’re feeling stop you from doing what you know is right. This is especially important when it seems like no one is returning your calls, replying to your emails, or texting you back. Keep plugging away!

3. Pace Yourself

When I left State Auto Insurance some people thought I retired. That’s a laugh! Whenever someone innocently made that comment my reply was, “I didn’t retire. I work harder now, put in longer hours, and work more days than I ever did in my corporate roles.” 

When you’re on your own there’s never a shortage of things to do! For example, I’m getting ready to launch book #2, am knee deep in book #3, will be building out more online training, and I’m going to put a “studio” in my home to give better presentations, all while I continue marketing to current and prospective clients.

Takeaway. If you had the energy and ability you could work 24 x 7 x 365 when you’re on your own. But the reality is nobody can do that so you need to pace yourself and create a schedule that allows you to rest, recharge and stay connected. 

4. Be Ready to Pivot

When people ask how business is, I jokingly say, “Great considering we’re in a pandemic.” While 2020 wasn’t what I…you…anyone…expected, I’m very fortunate that year #2 was a good bit better than my first year. Not many businesses can say that right now. Even in normal times many new businesses fail after a year or two.  

Like so many businesses, I’ve had to pivot in a way I never anticipated. There were no conferences to go to and in person training all but dried up. Nobody knows when either will come back so I’ve decided to put a studio in my home so I can give the highest quality online training and virtual keynotes. Thank you David Avrin and Mark Henson for the inspiration and advice on this one.

Takeaway. Nothing stays the same and nobody knows what the future holds. Look at what other businesses are doing and ask yourself if you can take some of their ideas or activities and use them in your business.  

5. Enjoy the Ride

While insurance remains my focus, I’ve enjoyed working with clients in pharma, oil & gas, healthcare and other industries. I’ve met people from around the world, learned new things and have had fun applying what I’ve learned over the decades in new ways. What I’m most thankful for and have enjoyed most are the people I’ve met along the way.  

Takeaway. All work and no play can make for very dull days. Leaving the safety net of a business to strike out on your own means you’ll need to rely on new people to help you. That means building new relationships which can be fun and exciting. Trust me, there are lots of good people who want to help and work with you. 


I’ll end by sharing a couple of resources I found very helpful as I got ready to make my move. Dorie Clark’s books Entrepreneurial You and Reinventing You will help you think through many aspects of branding yourself and stepping out on your own. 

Brian Ahearn, CMCT®, is the Chief Influence Officer at Influence PEOPLE, LLC. An author, TEDx speaker, international trainer, coach and consultant, he’s one of only 20 people in the world personally trained by Robert Cialdini, Ph.D., the most cited living social psychologist on the science of ethical influence.

Brian’s book, Influence PEOPLE: Powerful Everyday Opportunities to Persuade that are Lasting and Ethical, was named one of the 100 Best Influence Books of All Time by BookAuthority. His LinkedIn Learning courses on sales and coaching have been viewed by more than 100,000 people around the world.

Keep an eye out for Persuasive Selling for Relationship Driven Insurance Agents in January 2021.


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