The Number One Best Thing about Being a Business Owner

You’ve heard this one, I bet: Being a business owner is great – you can work any eighty hours a week you want.

Like all jokes, there’s truth to it. In the height of the winter holidays, for example, Dean and I can easily go weeks without a day off. Getting home for dinner by 9:00 feels like a real treat. 

And please don’t hear this as a complaint. As business owners, we’re grateful for the busy days. It’s a key indicator of success. It’s like that other old saw: “The reward for work well done is the opportunity to do more”(Jonas Salk). Ain’t that the truth!

Like anything, there are good and not-so-good aspects of owning your own business. For us, chocolate is our focus – making, selling, and connecting with customers. But whether you want to start a tech company, open a car wash, build a better toaster, or solve the climate crisis, you’ll run into the same challenges and experience many of the same joys. If you’ve ever wondered whether to quit your day job and jump into the entrepreneurial fray, here’s a cheat sheet that I hope can help:

The Toughest Things about Being a Business Owner

• Uncertainty. It’s guess work. Deciding what to invest in always is. There are always a million choices for which path to go down, what to focus on, and how to spend your time and money. The last 18 months of the pandemic has told us, as if we needed to be reminded, that there’s no certainty, ever. And when there’s health riding on it, decisions take on a different heft. 
• You have to do it all, at least in the beginning. When you’re starting out, you’ll do your own dishes, mop your own floors, and take out your own trash. We still do all of that, and we’ve been around for 17 years. It’s not difficult, but it’s also not the work most of us love or why we start a business (unless you’re a cleaning business, which we value very highly!). Then there’s the bookkeeping and the taxes. Again, that’s not what we’re good at or enjoy, but it clearly must be done.
• You don’t have just one boss. Yes, being your own boss is hugely positive. Back before Dean and I started Dean’s Sweets, when I had an office job, it used to be a real pet peeve of mine to have to “ask permission” of my boss to leave early for a dentist appointment. Now, even though I don’t specifically have to ask permission from anyone, we do, in a sense, have a million bosses. Every customer that walks in the door, every person that orders through our website, every phone call for curbside pick-up is someone we need and want to serve as well as possible. That’s a lot of people telling us what to do, and a lot of people evaluating our performance. With social media and the ability to get feedback from a lot of different sources, we have a lot of bosses. 
• No paid vacations. Bummer. For that reason, we didn’t take much time off for the first seven years of starting our business. But as time went on, we were able to hire a few incredible people to help us day-to-day, and we were able to eke out some days off. And depending on your business, maybe there’s still an income coming in even while you’re away. Think about that possibility! 

The Best Things about Being a Business Owner

• You see what you’ve created. There’s a real sense of pride when I look at what we’ve built over the last 17 years. Every chocolate creation, every box and tag, we’ve made from scratch. We have extraordinary help – we work with designers and website professionals and amazing photographers (thank goodness!) – but every idea starts in our brains somewhere. I remember putting flavor labels on the plates in our display case. I made those on the first day we opened our first store in November, 2008. They are still in use today. “Built to last,” as the business writer Jim Collins would say. That’s something to be proud of.
• We have creative license. We don’t have to run our decisions past anyone. If we want to make three kinds of hot chocolate, and 30-something kinds of truffles, and a party pumpkin, we can do that! In that regard, we also have the freedom to make any mistakes we want too. Have we told you about the blue cheese buttercream? You can read about it here.
• We can have all the chocolate we want. If we owned an ice cream shop, we could have all the ice cream we wanted, but we’ll just have to settle for chocolate right now. 
• We get to hang out with great people. Our employees are flat-out the best. They bring cheer and laughter, creativity and great ideas to our lives. They catch our many mistakes whenever we make them. They make us better, smarter, happier chocolatiers. 

The Number One Best Thing about Being a Business Owner. 

The number one best thing is creating a work environment where everyone feels safe, heard, and seen. This may not be an obvious perk of entrepreneurship, but over the years, this has emerged to be my favorite thing about being in business. It’s personally gratifying to support our employees and to see them thrive. At its most basic, this means taking the time and setting policies that show we care, and then to stand behind them. It’s not always perfect, for sure, but we strive to encourage the whole person to come to work, not just an outline of someone who punches a timeclock or shows up for a work shift. Instead, we value the freedom for each of us to be who we are, with ups, downs, concerns, and lives outside of work. 

There are times, no doubt, when we leave our personal issues at the door because there’s so much work to be done and we just have to do it. But when there’s freedom to converse while we work, I prize the idea that we can be real. That doesn’t mean dumping on one another, and that still means we all have appropriate boundaries. It does mean that if there’s something to talk about, we talk about it. If someone is worried about a parent or a child or a dog or a cat, we have the space to let that subject be in the room with us. 

I also love that our employees get to focus on things outside of work that are important to them. It’s such a win-win. Mostly that has to do with being flexible about work hours. It sounds simple, doesn’t it? Well, it is. We have one employee who is passionate about gardening. She works fewer hours in the summer when her enormous backyard garden needs her most. Another employee is a wedding and portrait photographer. Both of these great employees work more for us in the winter than the summer, which is perfect for our busiest seasons November through May. If someone has family coming to visit, we cover for them. Then they cover for us when we go off for a few days. This kind of flexibility is strangely unusual, or so I’ve been told. Not every business can do this, I get that, but we can, and it makes for great, productive, and long-term working relationships. 

Twenty years ago, when I got an MBA, I took a human resources class. In that class, we were warned to never refer to any employee as family. So, for example, we were advised to resist saying, “so glad you’re part of our Dean’s Sweets family.” The reason given is that it’s much harder, if not impossible, to discipline or fire a family member. According to this thinking, an employee should be kept at arm’s length so that we don’t stumble over emotions when having difficult conversations. I tried living that way for a few years, but it just didn’t work for me. I’ve realized, I care about people.

Now, instead, once we hire someone and we build a working relationship over time, we also build a personal one. We care what they think and feel, and we do our best to support them. It is like a family, or maybe even better. We make our employees’ happiness as important a priority as making chocolate and selling our products. This is as crucial in a good economy as in a lousy one. In return, they care about us, and their jobs, and the business, and they stick with us for a long, long time. Best of all, we get to see the people we work with happy and whole. Creating an environment where we are all safe, heard, and seen while creating incredible chocolate – that is the number one best thing about being a business owner.