Why being someone’s boss is the hardest part of being a small business owner

It’s hard being a boss, and to tell you the truth, I don’t know if I’m cut out for it. 

I’ve always been a member of the team or a lone wolf, freelancing and managing no one but myself. 

To be honest, I kind of prefer it that way. Managing anyone but myself is a real test of patience and to do it well feels like a true art form. Sometimes I don’t think my self-esteem can take it. 

But moving into owning my own small business, our team keeps growing, and I find myself with more and more young people under my wings. 

Being in hospitality, I’m in a very young industry, and by that I mean by its nature, we are leading a group of teens and 20-somethings. They’re in that fun and frivolous stage of life, where they’re really discovering who they are and still, I would say, testing the boundaries, at least professionally.

Ask any small business owner and they’ll tell you – people are the hardest part. There’s no HR manager to lean on, no committees or departments to delegate to – just my sister and me, navigating the very complex world of personalities and emotions. 

Balancing being both authoritative and friendly

What I find hard is navigating the balance between being both authoritative and friendly, professional and personal, serious and playful. 

The thing is, I really like my team. I wouldn’t have hired them if I didn’t. And, for the most part, they all like each other – they’ve got their own group chats and nights out and movie dates, which is so heartening. But it’s a strange and new sensation to be the one left out.

I was on every social committee of every business I ever worked in. I was the first to head to Friday drinks and the last to leave. I looked forward to the Christmas party every year with great enthusiasm. 

In a way, of course, it feels like the natural progression of things – just like we would feel odd returning to high school as a student (and who would want to). When you step up, you grow out of that phase of being one of the crew. Whether you like it or not, you’re in a different category of being.

It’s one of those instances in life where all of a sudden, you realise you’ve gotten older. And it catches you by surprise.

Fairness and pursuing the greater good

Sometimes, there are tough decisions to be made, for the greater good of the team. 

People often view scenarios from their own perspective, and so in someone’s eyes, you’ll inevitably be the bad guy. 

In my business, we have tried to foster an environment where we encourage everyone to be open with how they’re feeling and to let us know if anything untoward happens when we’re not around. 

We’ve had wonderful, frank, open conversations with our team, which helps us keep trying to create a happy and supportive work environment. 

But, not everyone is going to get along. And in that case, there has to be careful navigation to shepherd the team in such a way that the environment stays as calm, safe and productive as possible. 

It takes great care and great tact, and it’s hard to always try to get it right.

Keeping things close to your chest

It’s a challenge to be completely transparent with your team. This can be due to things being told to you in confidence or just the realities of business that they don’t need to be privy to.

This can mean that you often can’t show the whole picture that leads you to your decision-making.

My sister and I often note that we tend to know more about what’s going on in the team than they might think we know.

It can feel unnatural to our personalities to be so guarded, but necessary for the roles that we are in. It also helps build trust – our team knows that they can come to us with anything and we won’t use it against them or let it be heard by unwelcome ears.

You’re always a mediator, always thinking about what information needs to be shared and what doesn’t, and how best to do it.

The thing is, management comes with its challenges, but it is also so rewarding, too. It’s buoying to meet such bright young minds, to feel their youth and enthusiasm for life, and to see them grow and develop, eventually, moving on to their next chapters. 

And while it’s one of the tougher roles I’ve taken on, I hope to leave a positive and indelible mark on their characters and careers. 

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