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

By February 26, 2014February 1st, 2018Marketing Insights & Strategy
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.

Join the discussion 14 Comments

  • Learning to delegate is a huge hurdle for so many of us small biz owners. I don’t think we can ever hear this message enough. A great follow-up post to this would be how to make it happen — how to plan for, budget, hire, etc. the right people. Make it a series! It would be a fabulous ebook, too. (Try to stay out of those wind tunnels, would ya?)

    • Oh yes, delegating is hard. Sometimes harder than just doing it! There’s the ownership problem (My business! I do!) and the guilt problem (I can’t make someone else do something I won’t) and the control-freak problem (Nobody will ever do this as well as I can) And somewhere in there is probably training. But it’s snowball-ish. You get better the more you give away 🙂 I might just write that one!

  • ooooh I love your suggestion of sticking to the mode you are in. I am definitely going to take your advice and stay in that mode for the day…I believe that is where I go wrong, I keep trying to shift and often it does not work. On the other side of it I have to forgive myself in between when I can’t shift gears…too many times I have felt bad because of it..but I get it’s the bundling of similar items that will help get more completed effectively. All those hats sure can make one dizzy and nothing get’s accomplished. My new goal for the 2nd quarter is to find another person to delegate too as well. I finally did that for the bookeeping/finance part which has lifted such a heavy load off… I loved this…as usual!

    • It’s so hard to switch gears! On days when I do and I jump from this to that I always feel dizzy by then end and like I got nothing done. It’s so much better for your brain and productivity to focus on one type of task, even if you switch tasks, but stay in the same family!

  • I so hear you on the “I’m an entrepreneur, not a bookkeeper” thing. I’m lucky my wife lets me out of the house with a wallet, let alone credit cards to go with it.

    When April tax time rolled around, my roommates would post a count-down clock indicating how soon I’d be going to jail. The day I could afford to hire a bookkeeper AND an accountant was the day my life took a turn for the better.

    Not only do I have monthly profit and loss statements, I have a better idea of how money works in my business (it’s not a perfect understanding, but I can at least keep the needle more towards the green side than it had been).

    Also, along your note on no production work during prospecting meeting days – I was *supremely* frustrated today because it was the SECOND day I had to go out and about and meet folks, which invariably led to folks abusing their time privileges with me (how many times do I have to hint that your time is up, dude?), and me running behind schedule for the next person who’ll do the same damn thing (happened 3 times today).

    I’ve been really good lately about setting ONE meeting day per week, whenever I violate that, I invariably regret it. A meeting day is a day that no work is getting done – no productivity is happening. Maybe you land a new client or get an idea clarified, whatever – but you’d better plan on NOT getting any good work done that day.

    • You and my husband are in the same boat. I don’t think he even knows how to sign a credit card receipt 🙂

      I agree that meeting days are no good for production for more than one reason. No meeting has ever gone the length it was supposed to. One hour meetings last three. And your brain is never in the right place. I never ever ever schedule more than one meeting on a day. More than one phone call is bad enough!

  • Work it Carol Lynn, work it! And no, that hat doesn’t not make your butt look fat.

    This is a post that I’m going to come back to again and again. Wise insight on rocking our unique Brilliance in the world.

    Big love,

  • It can be so hard to let go of things. For me it’s either, “I’m smart I can figure this out. (Streaming video hates me on purpose!)” or “I can do this and I do it well. Why would I pay someone else?” That is the path to feeling overwhelmed and underpaid. I made a goal last December, 2014 is the year of delegation. It’s hard, but it’s working. Thanks for the reminder of why I’m doing it.

    • It is hard! You really have a sense of owning it all – your biz, your stuff. So giving it away seems like you’re just not doing your job. But seriously, you get used to it 🙂 My assistant is my new best friend. I keep her list long and that gives me brain space to focus on the business, not on every detail and every bit of production.

  • I love your post, Carol Lynn, especially for the visual imagery it evokes. 🙂

    As I made my way down the page, I kept envisioning a tall stack of exquisitely designed hat boxes in the corner of your office. Not only are they a design element in the room, but also representative of all the duties/chores/tasks involved in owning and running your own biz.

    Let’s just call small business ownership “Millinery Madness”! LOL!

    • I love it, Melanie! I think we should have someone talented like Evan draw us a poster 🙂 And now that you mention it, I think I want some hat boxes in the corner of the room!

  • Monotasking and focus go a long way to helping you get stuff done, for sure, Carol Lynn. I’m definitely a many-hatter, easily distracted by email and other stuff. But when I focus for a while, things go better. Getting rid of notifications that pop up and disturb you can be a good first step.

    • Email is the worst! I always get more done when I just shut it and pretend it’s not there. It’s a little mini-ADD symptom in a box. If it’s open I check obsessively!