What I Learned about Entrepreneurship from "Take Your Child to Work Day"
Today is Take Our Sons and Daughters to Work Day—a day that will always remind me of long, hot Boston summers doing manual labor on construction sites. My dad was an entrepreneur who ran a construction company, and from age 6 to 15, I spent my summer days on the job, doing everything from observing to fetching coffees to learning how to wield a hammer and cleaning up a construction site. While I was there, I was expected to pull my weight—no excuses tolerated.
Those summers changed my view of my own professional path and taught me a lifetime of lessons about entrepreneurship, especially now that I’m building my own business. Here are a few of the big ones.
1. Fight Through the Rough Patches
There are times when things in your business just aren’t working—maybe you have tough client or the wrong staff in place. But during those times, you can’t give up. On the contrary, you need to learn, up your game, and push harder to take things to the next level.
One time, I witnessed one of my father’s clients fail to pay him on time, which jeopardized a month’s pay for more than a dozen families who relied on the crew’s wages. And then I watched my dad, after some complex wrangling, secure an advance on another job that then required him to personally work weekends for months to complete. It wasn’t easy, but it was what he had to do. When something isn’t going according to plan, you need to fight it out and find the energy to change course.
2. Distinguish Yourself from the Competition
When all the firms in your space are competing for the same business, you’re often forced into a price war. But do that, and you’ll end up in a race to see who can go broke the fastest. Instead, you need to find a point of differentiation.
In the construction business around Boston, my father’s major competitors scrambled for big jobs in high-end communities. He, on the other hand, took smaller, less glamorous jobs in rough neighborhoods. By doing so, he built a reputation around a specific clientele and was able to leverage that into a long-term customer base. Looking for opportunities where others don’t, or solving similar problems in new markets, is often a much more effective strategy than trying to compete on price.
3. Be Careful of Friendships
When you’re in the trenches of building a company, you often form deep friendships with your employees and colleagues along the way. This is one of the best parts of running your own show, but it can also be one of the hardest. Tough decisions and conversations are sometimes avoided out of fear of offending one another, and transitions that are natural in the evolution of a business can get delayed.
My father found a longtime ally in a struggling alcoholic nicknamed Rookie, who I remember most for a love of baloney sandwiches and a willingness to show up and do the hardest jobs, on short notice, with no complaints. But eventually, his drinking and drug abuse were interfering with safety and client delivery, and it came time that they should have parted ways. My dad just couldn’t do it—and as a result, he lost a number of jobs, which had a significant financial impact on his business. He learned the hard way that, when you’re working with friends, you still need to make sure that the lines of friendship and business are clearly delineated.
4. Set up Systems and Support
The freedom to determine your own schedule and be fully responsible for your own success is why many people become entrepreneurs in the first place. But when you add client demands, staff needs, administrative processes, and everything else it takes to run a business, your “free” spirit can start to suffocate. It can actually feel worse than when you worked for someone else.
My father was amazing at dealing with customers and conceptualizing and selling remodeling jobs. But administrative tasks like payroll, human resources, and taxes were his Achilles heel. It took a serious legal problem connected with the IRS before my father learned this valuable lesson: Spend time doing only those things that you do well and hire others to do those you don’t—even if it means you sacrifice a bit of profit to do so. Understand your strengths and weaknesses, and find ways from the beginning to complement your team with others who fill your gaps.
5. Design a Life that Works for You
For my dad, freedom was being able to ride around in his beat-up pick-up with the windows down, coffee in hand, AM radio blasting, and no destination in sight. It’s likely that your definition is different, but being an entrepreneur gives you the opportunity to ask how you really want to live your life. How do you want to spend your time? Do you want to be mobile, working as you travel the world? Do you want a giant house, a fancy car, or the flexibility to spend a year in Hawaii? Maybe you just want to be home at 2 PM to meet your kids at the bus. Take the time to figure out the kind of life you want to live, and then build the business around that to enable your dreams.
The lessons that I learned watching my dad weren’t always easy. But spending those summers together opened a window for me into his life and his business, and it taught me things I couldn’t have learned in any other way.