Wear That Hat (And The Other One, Too): A Small Business Owner’s Guide To Staying Sane

I admit that as I write this I feel like the last person on earth who should be dispensing advice on keeping your hat on when the wind blows. There so happens to be a whole lot of blowing going on around here right now, some business related and some personal, some that is simply flotsam gusting in from other people’s lives and landing in my path. And I spend a lot of time chasing my hats down a dark and narrow street.

But in between, I manage bursts of sanity, so who better to dispense advice than someone who knows what it’s like to wear the myriad hats of a small business owner and occasionally still walk into a room with perfectly coiffed hair?

So today, as my Word Carnival group tells stories of service and “necessary but dirty jobs”, I decided to share the tips and tricks that help me run a business, balance the responsibilities it requires and sometimes even come out on top.

Which Hats?

There’s a good chance that if you run a small business you’re alternately CEO, customer service rep, marketing professional, operations manager, bookkeeper, receptionist and toilet scrubber.

You’re probably also the sales person, content creator, IT department and the guy who runs out to get bagels.

On any given day you’re responsible for purchasing, prospecting, networking, billing, production and so many other tasks that it would get a bit overwhelming to start reading them all in a list here.

I’ll save you the angst.

But if you want to wear your hats with aplomb then you do have to define them. The list is probably scary. The act of creating the list is probably scary, too, because that means you actually have to sit down and take time away from balancing the rest of your hats to take on the role of Chief List Maker.

And yet… what good thing has ever come easily? It may be tough to grasp just how many things you do but I promise that once you see it in black and white in front of you, a couple of things will happen.

One, you’ll cut yourself some slack for missing that deadline yesterday when you realize just how much you’re juggling. A little imperfection never killed anyone.

Two, you’ll start to recognize just how awesome you are for doing so much. And if you don’t, just tell your mom about it and she’ll think you’re awesome and hearing that praise will do you a world of good. Trust me on that one.

Three, you’ll be better able to organize it all and to figure out a way to do the necessary tasks without losing your mind.

So before you move on to the rest of these tips and ideas, you need that list. Without it you’re just blowing in the wind.

Which Hat Matches Your Eyes?

Once you understand all the hats you’re wearing you can start paring down. You’ve tried them on, now figure out which one matches your eyes and brings out the highlights in your hair.

In other words, which one best matches your skill set and your passions?

Bookkeeping is not my strong suit. Just ask my accountant. Our conversations usually go a little something like this:

Me: Quickbooks just did something.

Him: What happened?

Me: I don’t know, but there’s suddenly negative six thousand dollars here.

Him: Well, you must have entered something wrong.

Me: No, I didn’t. Quickbooks hates me. On purpose.

Or something like that.

So I don’t pretend to be a bookkeeper. I know better than to spend a lot of time figuring it out or getting cozy with it. It’s just not me.

It’s what you call a necessary evil but instead of trying to be the next Quickbooks guru, I recognize my limitations and take a “call the man” approach to getting the bookkeeping done.

No, I can’t hire a bookkeeper, but I can “call the man” if I spend more than ten minutes trying to unbalance a checking account.

One of the pitfalls of wearing all these hats is thinking that we have to. Or that we should. But if something is not your strength, if it sucks up your time or energy and you have a nagging sense of guilt about not doing your job well… I’m here to tell you to let it go.

There are so many hats. Don’t get attached to the ones that make you look fat. But when you do find one that suits you, wear it proudly. Be that person and be good at it. Spend your time and energy learning and perfecting that skill and remind yourself repeatedly of how good you are at it. So what if you’re a terrible bookkeeper? You’re a kick-ass, rockstar writer, so there.

Which Hats Are Most Important?

It’s all about priorities. Sometimes you have to wear the hats that you don’t love, even the old, ratty, ugly ones. After all, when you’re a business owner you don’t get to say, “That’s not my job.”

It’s all your job, right down to scrubbing the gunk out of the wheels on your chair with a toothbrush.

Just saying.

But that doesn’t mean that all of those jobs are equally important, or equally important for you to do.

And yet it’s so hard to give up those hats! Yes, even the old, ratty, ugly ones. We get sort of attached to them. We own them. We freak out when they’re gone because we suddenly feel very naked without them. And yet they weigh us down and wreak havoc with our hair.

If you really want to grow your business (and stay sane while you do) then you need to spread the hats around a little. That might mean to another team member. Or to an assistant. Or to another company.

Think about which things require your attention. Maybe you need to be the voice of your company on social media, and so you must spend time checking on your social networks every day. But do you really need to be the one tagging and shortening URLs or setting up the schedule in Hootsuite?

You need a chain of priorities so that you know where your skills and presence are required and what you can delegate to someone else. When you come across something that you can delegate, do it.

I know what you’re thinking. “I can’t afford to hire someone.” I thought the same thing. For a long time I did every task big and small, the ones I had studied for years to perfect and the ones most people can do in their sleep. It made sense. I would get things done and wouldn’t “waste” money hiring someone to do something that I could do – in my sleep.

But there are only 24 hours in a day and the more time I spent on things I didn’t need to do, the less time I had for big-picture important stuff. Like working on my business. Like getting even better at the things I was passionate about.

I’m not telling you to delegate things that are “beneath” you. I know how the guilt creeps in here, too. You feel bad for making someone else do the “dirty” jobs. But I’m not telling you to ask someone to scrub gunk or toilets. I’m telling you to ask someone to take tasks off your plate that do not require your personal attention.

That will free up your time to do the things that have the most impact on your business and the biggest likelihood of making you money.

Pawn the rest off with impunity. And compliment someone else for looking pretty good wearing one of your hats.

Which Hat Should You Wear Today?

One of the hardest things I’ve ever done when it comes to running my business was picking a hat and sticking to it.

Let’s face it, we’re always going to wear a lot of hats. It’s just how business works. But it’s incredibly challenging to go through a wardrobe change two, three, six, twelve, seventy times a day. And yet that’s what we often attempt to do.

One minute we’re answering emails, another we’re picking up the phone to handle a client issue, immediately after that we get into production mode and later on we jump into a prospecting meeting.

It’s enough to give you an identity crisis. Not to mention a giant headache.

And so I worked on forcing myself to wear a hat and keep it on. Now, when I’m say, writing a blog post, and the phone rings, I let it go to voicemail. It is so hard. I just know there is a customer who needs something urgent. I’m pretty sure that was my last chance to close a deal with a prospect. I probably missed the call of my life, the golden opportunity, the million dollar check.

But when I’m writing a blog post I’m in creative mode. Not in prospecting mode or customer service mode. Yanking one hat off to don another just leaves me looking – and feeling and sounding and acting – sloppy.

As hard as it is, you must set aside time to wear your hat, wear it well, and then give yourself time to take it off, wrap it up all nice in a little tissue paper and put it back on the shelf so you can take out and wear the next.

Whenever I have a prospecting meeting I usually don’t schedule any production work on the same day. Sounds like a waste of time, right? A meeting lasts what, an hour or two? But once I’m in prospecting mode I stay in prospecting mode. After the meeting I may make a few more follow up prospecting calls. Or work on my contract. Or streamline my client intake process.

It helps to set aside certain times or even certain days for tackling your priorities. I designate entire days to nothing but bookkeeping because if I have to switch hats from that to blog posts or even customer service, hats usually get crumpled. Other days I designate solely to gunk-scrubbing. Others still to nothing but writing.

During any given day I set aside time for responding to emails and when it’s not email-hat-wearing-time I simply shut my email and don’t look at it. Believe it or not you do not have to answer every email within ten seconds.

I set aside time for social networking. I set aside time for production. Sometimes I organize my entire to-do list around the hat du jour. Sure, I have to finish that client website but if I don’t send out the internet bill there will be no site to work on.

Bookkeeping day, business development day, janitorial day. Email hour, phone call hour, production hour.

Figure out which works best for you. Then figure out which hat you’re going to wear right now, today. And once you choose it, step away from the closet and get out there and wear it like you mean it.

Work That Hat

Skills, priorities, delegating and this crazy little thing called monotasking will go a long way to keeping you looking pretty in your hats instead of like a big, frazzled mess.

I can’t say I’ve perfected it but these are the things that keep me off the funny farm. With a little bit of practice you can walk that hat down the runway and look like a star doing it.

How do you manage your multi-hat roles? Any special tricks that work for you?

This post is part of the monthly Word Carnival series of posts. This month, our carnies take on the topic of being in service to your customers and yourself, plus all the hard work it takes to do all those dirty jobs required of us as small business owners. Read the rest of the Word Carnival posts here for more great advice from some of the smartest business owners and entrepreneurs you’ll meet.