Dear Younger Self

Dear Younger Self,

Where do I even begin? You are about to embark on what may be the most challenging years of your life. I know the thought of our family business transitioning to the second generation – YOU! – fills you with equal parts excitement and dread. The thought of it might already be keeping you up at night. I know you are ready for dad to step back and terrified for him to do it, all at the same time. So know this – you will get through it all. You will be the one in three who makes it through this transition to the second generation with our family and our business intact. But I won’t lie, it won’t be easy and you’re going to make a lot of mistakes along the way. It’s okay, everyone does! Here’s what I wish I knew when I was you.

Listen. Really Listen.

Listen to dad, to mom, to the attorneys and the accountants. Listen to not only what is said, but what isn’t being said. Don’t listen to respond or to prepare to go on the defensive. Listen to understand, to empathize as best you can. Listen even when dad is being dad or you don’t agree with what the advisors are saying. Then, above all, listen to yourself. Listen to what you really need and want, not what you think you are supposed to want.

Jack of all Trades, Master of None….For Now

Buyer. Employee. Boss. Coworker. Spouse. Business Partner. And, most acutely, Child of a business owner. At any moment during this transition, you will wear every one of those hats – and usually all of them at the same time. Always be aware of the hat you are wearing, especially when the conversations get heated or the emotions run high (punctuated with a slammed door…or two). And don’t be afraid to take off a hat or two when you need to. Some days you will need to pause and simply be dad’s Child, no one else. That doesn’t make you any less of a Business Partner or a Buyer. It makes you ready for the complexities of being the Owner of our family business. This entire experience will make you more of a critical thinker, a stronger maker, and a better leader for our team.

Get Outta Here

Find a place outside of our family and away from our biz that supports you and energizes you. Look for people who give you the space to be vulnerable. Grow the circle of people you can rely on to include those who understand what it is like to live this crazy jumble of family interwoven with business but who don’t share our last name. I joined the Entrepreneur and Family Business Council at DePaul to have a better understanding of what owning a family business really means for all aspects of my life. I only wish I had joined sooner.

Stop Walking in His Footsteps

What dad built has obviously worked. We have a great company and lots to be proud of. But it’s okay to take risks and remake the company in your image, with dad as your trusty sidekick. Growing up, he would always say how much he enjoyed you working with him. Now you get to be the one driving and feel that same joy as he is along for your journey.

That entrepreneur spirit that pushed him to take this leap, is in your blood too. He felt the same nervous excitement that comes with knowing you’re responsible for your own success. You’ve watched and grown over the years to develop the critical thinking skills to face new challenges head on. You’re ready.

Know that we will all benefit from trying new things that you, not dad, create. And most of all, know that we’ll continue to grow together, as a business and as a family.

All my love,

Your Older Self