I always find the end of May a bittersweet period, with its focus on graduations and plans for the fleeting summer. It’s a time of celebrating the crossing of an arbitrary boundary we have created between “child” and “grown-up”. And, with The Bookkeeper having just celebrated our sixth year in March, I’ve been thinking a lot about what growing up means for a company.

What I’ve found is that, much like how many adults will confess to still really not feeling like grown-ups, I think it’s hard to pin down exactly what being “grown up” means for a company. However, there are a few things I keep coming back to.

1. You know who you are.

business woman shaking handsFor most teens, a major source of anxiety is whether or not people like them. Often they are either chasing popularity, or trying to conspicuously prove they don’t want it. Many new business owners start the same way. In the interest of making connections and gaining customers, they try to be everything to everyone. But comfort and maturity comes with knowing the work you like doing, what you do well, and focusing on being the best you can at that.



2. You choose who you surround yourself with.

man and woman talking on sidewalkWhen you’re younger, your friendships, though dear, form generally through default. Your best friends are the kids in your class or neighborhood, or with whom you play on a team or share some activity. When you first start a company and enter the social world of small business, you run into the same people over-and-over at networking functions, morning meetings, etc. Over time, you identify which of those people with whom you feel a real connection, and develop some great friendships. But at the beginning, you’ll make a lot of coffee appointments with people who don’t have your best interests at heart. Sometimes you’ll even know that going into the meeting, but you’ll feel too “new” to shoot anyone down. As you grow up, you learn to recognize the people with whom you want to spend your precious time, and you won’t feel hesitant to prioritize your calendar accordingly.


3. You’re unashamed to let your childish side show.

child with finger paint on handsYoung people go through a period where they are ashamed to play and then, at some point in adulthood (if they’re lucky), they rediscover the joy in acting like a kid. In your business, it’s important to keep that playful joy and remember why you love working for yourself. (We didn’t escape corporate to create corporate.) This doesn’t mean being reckless or irresponsible; it just means letting go enough to embrace the fun that comes with being a business owner. This can be something as simple as realizing it’s a beautiful day and you’ve got no afternoon meetings, so you leave the office to hit a few miles of trail (me). Or, it can be something as big as taking your entire team and all their families to the beach for a weekend (Craig). The point is that, without falling into the trap of anything as contrived as “team-building”, you find ways to enjoy the work, and the flexibility the work gives you.

Of course, just like a graduating high school senior who thinks they’re grown, I might have no idea what I’m talking about. When The Bookkeeper is 10 years old, or 20 years old, or, should I live to see it, 50 years old, I might look back and laugh at my own youthful naivete. All I can do for now is look forward to what I’ll know then.