This week I’m down at the beach with my family — including my mom, stepfather, brother, and sister-in-law. It’s the first vacation I’ve had this summer.
And whenever my mom, brother, and I get together, it’s often to the dismay of our significant others, who respond by retracting from the triplex vortex that is always created when we share space.
It manifests itself by us screaming the same stories to each other that we’ve told for the last 30 years so loudly and repeatedly that no one else can fit in a word (hence their retraction). Most of the time, our stories are about other family members. At least historically they have been.
But now, we dedicate a lot of our vent sessions to business.
Each one of us is self-employed, which is probably not an accident.
Because each one of us loves what we do and are passionate about our work so much that it naturally attracts our clients. But mostly because we have control issues and don’t want a boss telling us what to do.
My mother is a real estate owner and agent. My brother is a caterer (here in Orange County, by the way!), and I am, well… a filmmaker, writer, speaker, consultant, landlord, and probably several other things that I can’t remember right now. My mom has the largest company with somewhere around 40 agents now, but it took her about 20 years to build that. My brother’s company is next in size with a handful of full-time employees and a long list of subcontractors for his weddings and events. I’m the smallest with me being the only salaried person for the company and two part-time employees.
But even though our businesses are very different from each other, they are all just extensions of who we are as people and we didn’t choose them, so much as they chose us.
To see us talk about our work is to understand why we do it—each one of us is so passionate that it spills out when we describe every cute house we just sold, or wedding we just catered, or speaking gig we just delivered.
And we’re just as passionate when things go bad.
Running a small business is challenging and it’s not made for everyone. We do it because we couldn’t do it any other way. And if you’re considering it, there’s a few things you should know.
It’s full of times that stress you to no end.
You will have months where you don’t know if you’re going to be able to pay your payroll, or where you have to dig it out from some other source you didn’t want to tap into.
You will have time where you’re on the verge of tears because of the enormous amounts of stress put on you to succeed, achieve, and proceed even when you want to just quit.
You will have what we call “Hell clients” that ask and take and take and ask, at all hours of the day, while crying and complaining about any dime spent and why the job isn’t going as well as they imagined it would in their minds. They’ll have ridiculous requests and ideas and then blame you when they don’t work.
(Our favorite “war stories” to tell in our vent sessions are those of our Hell clients.)
Your business will not just put strain on your life, but those of your family, too. Your wife or husband will inevitably get sucked into it. My stepdad is often doing handyman work for my mom’s houses before a sale, my sister-in-law has worked front of the house and back of the house for my brother, and my wife has worn a branded shirt at several events as part of my “staff.”
But it doesn’t end there—and I mean both the stress on your family, or the way the business consumes your life.
You’re never really off work.
I’m writing this at 5:00am while everyone’s asleep. My mom’s been sneaking away to make calls and is pretending like she isn’t. And my brother co-opted the photographer for our family photo session yesterday to take pictures of the shrimp boil he cooked to use for his catering company.
It’s all the time. It’s always. And it takes all of you.
So if you’re thinking about going into business for yourself (like a lot of people are these days), go for it! There’s nothing like being your own boss in a business that you love.
Just know that business is a lot like family.
You can love it with all your heart, while simultaneously feeling like it’s suffocating you at times.
Rain Bennett is a two-time Emmy-nominated filmmaker, writer, and competitive storyteller with over a decade of experience producing documentary films that focus on health and wellness. His mission is simple: to make the world happier and healthier by sharing stories of change.
You can read the rest of “Right as Rain” here, and check back every Wednesday on Chapelboro for a new column!
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