The Case of the Mysterious Entrepreneur

I’ve chosen the uncommon career path and lifestyle of entrepreneurship. You might be thinking “It’s not that rare! I know several entrepreneurs.” Maybe you do, but the stats I have found all say that around only 14% of the population are entrepreneurs, so it’s really not that common. And I’ve made things even more complicated for people around me by not only a being an entrepreneur and small business owner, but a working snowbird. That (currently) means I spend April until late December in Newport, RI, where my business is based, and late December until April in Charleston, SC where my happiness is based (kidding).

I get it when someone who is hearing about my snowbird life for the first time doesn’t get it. It’s weird and usually something only retired people do (although they get the pleasure of not working while they snowbird). But when my close friends or people who have heard it several times don’t get it, I have to say, it drives me a little crazy. And that’s how this blog post was born.

I don’t think the snowbirding confusion is because people don’t understand how that works. No one seems to have an issue comprehending how someone could live in one area of the country for part of the year and another area for the rest of the year. Many retirees do it, as well as boatloads of people in the sailing and yachting industries (excellent pun) and some people who work in the service industry. What, you’ve never met a bartender who works in a Martha’s Vineyard/Cape May/Ocean City bar during the summer then heads to Key West to sling dranks during the winter? Sure you have.

I think the confusion comes in due to the mystery of the entrepreneur. It’s easy to grasp that someone who works on boats could go from Annapolis in the summer and early fall to the British Virgin Islands in the winter because that’s where the jobs are. Or how a Cape Cod bartender could fly down to Florida to bartend there when the Cape summer season ends, because the Florida summer season never really ends. The guy who works on boats needs to be where the boats are, and the gal who bartends at one beach bar in MA can probably do it at a beach bar in another state too. But what does an entrepreneur do when they go somewhere else? That’s a great question that you didn’t even know you had, and it really depends on the business they own, but there are some general things all big bosses have in common.

When I tell someone I own an onsite hair and makeup company and I go to or am in Charleston for the winter, they often then say “Do you work while you’re in Charleston?” It’s flattering that people think my business is doing well enough that I can just not work for three months, but that is not the case. (Yet.) Of course I have to work during the winter! I own a small business! You think this thing runs itself? (Give me another ten years to get to that point.)

While I may not take makeup clients when I’m in Charleston, doing makeup is only about a max of 35 hours of my week during my busiest months in Newport. The bulk of my time is and has been for several years now spent managing, doing admin tasks, recruiting and hiring, and growing my business. Sure, taking out that client piece for three months and the fact that we don’t have many weddings I have to coordinate during the winter means I only have to work between 30 – 40 hours a week while I snowbird (which feels like a vacation to me), but I still work every single day.

I’m going to share with you some of things I regularly do during my warmer winters, not because I have some strong desire for you to know what my life is like, but because if you have any of those fourteen-percenters around you, they are likely doing a lot of the same or similar tasks but might have trouble articulating that. So while they are probably busting their ass doing all the mysterious work, you might be picturing them sleeping until 11:00am, answering a few emails, going to the gym, making a couple phone calls, posting on Instagram then calling it a day.

And now, a short list of some of the many regular things that fill my weeks when I am not doing makeup (both when I am in Charleston and in Newport). The entrepreneur in your life is probably doing a lot of the same or similar things, plus maybe several that I haven’t thought of.  If you’ve made it this far into the post, you might as well keep going.

Booking. A giant part of my job is booking weddings, wedding trials, events, commercials, shoots, makeup lessons, etc. If you think a client emails and says “Can you do the hair and makeup for my June 1st wedding?” and I say “Sure. See you then!,” you are dead wrong. I spend an average of two hours per bridal client checking availability, sending makeup artist and hair stylist portfolios and answering questions about experience, giving rates, answering emails, sometimes having phone calls, sending contracts and answering questions about those, and a lot of things I’m probably forgetting. (And that’s nothing compared to the time I spend once they are booked!) Any entrepreneur who provides services will spend some amount of time (or pays someone to spend some amount of time) on the booking process. Sure, some of them have it automated, but the system they use didn’t create itself. If you are not an entrepreneur but you work in Sales, some of this is probably sounding familiar to you.

Social Media. Some day, I will pay someone to do this for me, but until then, it’s all me (and I know that’s the case for a lot of entrepreneurs). For my company, I manage two Facebook pages and one Instagram account. I post on each three times a week, because consistency is key with social media. That’s a lot of content I have to come up with, and I of course have to be aware of new trends and algorithms. We get clients who have found us on social media, which is how I know it’s an effective form of marketing. I’m not in it for the Likes or followers. I’m in it to share photos of our work, beauty tips that can help people and information about the company, for those who are interested. It’s also an important way of getting our voice/brand out there. I think it’s fair to say that most business owners spend a decent amount of time on social media, or they pay someone to do it for them (and there is still work that needs to be done, even if you outsource it).

Blogging. I spend a few hours each week blogging. I didn’t always do this–check out the Archives from earlier years when I posted maybe once every couple months–but last year I decided I wanted to up my blogging game. I made a goal in 2018 to publish one post once a week, and I achieved that goal. I plan on continuing that once-a-week posting in 2019 and so far, I’m on track. I know blogging (and definitely consistent blogging) isn’t something that all entrepreneurs do, and in some industries, it wouldn’t make sense to. But I have valuable, expert info I want to share for free, and this is the platform for it. If the business owner in your life also has a blog, know that it definitely takes up a bit of their time.

Invoicing. We gotta get paid, you know? Invoicing is (or should be!) a part of most service-based industries. Even with invoicing or accounting software, it takes time to create, send, collect payment and follow up as needed (it’s often needed). Sure, the bigger the business, the more likely this task is to get outsourced, but freelancers and owners of smaller business will usually take care of this themselves. I can get most of my invoices done in under 10 minutes each, but I sent out around 300 invoices last year, so you do the math. (Really, please do it. Because I can’t.) If an entrepreneur has a good system in place and the company doesn’t have a complicated pricing structure, this shouldn’t be the most difficult or time consuming of the money tasks, but it is an essential part of the job.

Paying Bills. Money comes in, money goes out. It’s a vicious cycle. All entrepreneurs have some bills to pay, no matter how small their company is. Cell phone, WiFi, office space, advertising, personnel, inventory, etc. Some companies have a lot of overhead, while others don’t. But there are a ton of things that need to be paid for, and unless a business owner has someone doing that task, they are taking care of it themselves. Depending on the business, this can be a time consuming task, but it has to be done.

Taxes. Most of my friends are not entrepreneurs and from what they’ve told me, filing their taxes is usually not too complicated if they just have one non-Independent Contractor job and don’t own multiple properties. For entrepreneurs, taxes can be complicated. I have a great accountant and I meet with a bookkeeper from her office quarterly for Quickbooks reconciliation (think of it like balancing your checkbook, a reference you will understand if you were born in or before the early 80s). Even with that, I still have to send certain information to my accountant each year, as well as check that the 1099s sent to my Independent Contractors are correct and the 1099s I am supposed to receive have made it to me. Like many business owners, I pay quarterly estimated taxes, so taxes aren’t something I only think of once a year. I budget my quarterly payments, and now that my company has grown so much, there is other work I need to prepare every three months. I’m sure I’m not the only boss who does that. If you can spend one hour a year at H&R Block or wrap everything up in five emails with your accountant, I think that is awesome, and I am jealous. But now you know that one of the two certainties in life can take up more time that you might think for an entrepreneur.

Scheduling & Coordinating. I spend several hours every single week coordinating trials, meetings, assessments, trainings, sometimes corporate/commercial jobs and creating wedding and event schedules for hair and makeup. This time consuming task is part of any business that has services that are performed or people that need to show up to sell consumer goods. Things don’t just happen, you know? Someone–be it the business owner, admin assistant or a manager–schedules shifts/appointments/service times. Sure, some companies have scheduling software or set schedules, but that’s not appropriate or possible for all companies. I’m personally used to it and (I think) good at scheduling and coordinating, as I did some version of it at most of my pre-AB Beauty jobs. But a lot of people despise this task and struggle with it, so if you’ve got an entrepreneur in your life, this may be something they hate. But unless they can outsource it or can use scheduling software, it’s likely something they have to do to some extent.

Getting Photos. This is wedding-industry specific, but I’m talking about it anyway. (My blog, my rules.) Couples planning a wedding want to see pictures of venues, flowers, wedding gowns, table set ups, hair and makeup, etc. But since I’m a crap photographer at best, I prefer to use professional photos of the work my team and I have done. That involves getting wedding album links from clients, choosing photos that best highlight our work, getting the bride’s approval for the choices, contacting the photographer for permission to post and then posting them on Facebook and Instagram. Sure, the Facebook and Instagram part comes under my social medial tasks, but getting the photos is a whole different task. If you know a business owner who shares photos they didn’t take (and I really can’t think of an industry outside of the wedding industry that would), or hires someone to take photos for them, this is likely eating up some of their time.

Post-Job Follow-Up. I follow up after all wedding and event jobs we do, as well as after the first time I do or send an AB Beauty makeup artist to cover for me on a corporate or commercial job with a new client. As you may have noticed, many companies will send you a survey or ask for a review (review requests are part of my follow-ups too) after you use a service or buy one of their products. I think it’s so important to do whatever form of follow-up makes the most sense for a company so that clients/customers know someone cares about their experience after it’s all said and done. My guess is that most entrepreneurs do some sort of follow-up work.

Recruiting. I’m pretty much constantly hiring at AB Beauty. I post ads for new hair stylists and/or makeup artists, but I also recruit them from Cosmetology schools. That means I go in and speak to classrooms full of “future professionals,” as the Paul Mitchell schools call them, about AB Beauty job and training opportunities. This involves scheduling classes, preparing and updating talking points, answering emails after, etc. It’s an important part of my job and probably a part of the job for any entrepreneur who has a growing company that requires personnel. Depending on the industry, I can see this being anything from a minimally time consuming task that happens once in a while to something that is a top focus and can take up huge chunks of time.

Hiring. For any entrepreneur who has people working for them, hiring is on their task list (or something they pay someone else they have hired to do for them). Like with anything else, this differs by company and industry, but for me, it’s definitely one of the more time consuming tasks. Formal job offers, Independent Contractor Agreements, requesting professional license information and proof of liability insurance and about 35 other tasks are part of the process for me. From what I know, it’s a pretty time-intensive part of the job for most solopreneurs who have Independent Contractors or employees working for them.

Training. For business owners who have employees, training is (hopefully) part of the process. At AB Beauty, there are no employees but we do offer training programs for those Independent Contractors who are interested. These sessions take up several hours a week while the actual training is happening, but also several hours before it even starts to relay certain information and arrange sessions. If you’ve got an entrepreneur in your life who handles training, know that this can take up a lot of their time.

Accounting. I luckily have an accountant and a bookkeeper who I meet with quarterly, but there is still a lot of work I do that falls under what I consider the “Accounting” umbrella. This mostly involves entering information into Quickbooks, but anything that has to do with banking goes here in my mind. The entrepreneurs who hire people to take care of this can cross this task of their list, but a lot of us handle it (to varying degrees) on our own.

IT Stuff. One of my least favorite hats to wear as an entrepreneur is “IT Gal.” It’s not my strength but since, you know, everything is done on a computer, it’s something I can’t ignore. I have a company that handles my website design, domain and any website issues, which is awesome. And I have a freelance IT hero, Dan, I hire when there is something wrong with my computer. But before I go around throwing money at people, I research and try to fix some problems myself (and those are usually the times when you can find me drinking tequila to quell the frustration). Even if there is something I can’t fix myself, it’s still part of my job to reach out to the person who can fix it for me and follow through to make sure the issue is resolved. Sometimes Dan will walk me through fixes remotely, and I’m glad he is able to do that, but what seems like a simple problem can sometimes take an afternoon to fix. If you ever hear the non-tech entrepreneur in your life swearing at their computer, it might be because of this.

Taking Classes. If I ran my business like I did even five years ago, I’d be in trouble. Not that I was doing anything bad or wrong, but platforms change and businesses grow, so adjustments need to be made. For me, part of being a good business owner is learning about new ways to do things and approach the big picture and strategic parts of the job. I take a lot of online classes, workshops and webinars to help me better my business, and I know several entrepreneurs who do the same. These generally take up 60 – 90 minutes per class/workshop/webinar for online offerings, but in person classes can take an entire day or more. There is sometimes work that needs to be done before and/or after a class, so this can take up some time too.

I prefer online classes that I can take from my windowsill.

Personnel Communication. There is not a day that goes by that I don’t email or text at least one person on my team. (They’re like “Yeah, we know, Allison.”) Part of this has to do with the fact that they are all Independent Contractors so I can’t just schedule appointments without asking them. But there is a shit ton of other stuff that I need to check with them about (and that they need to check with me about), and I think all business owners who have people working for them handle this to some degree. So if your entrepreneur friend/spouse/relative has to step out of the room for five minutes to answer a time sensitive call from someone who works for them, give ’em a break! It’s part of the job.

Attorney Communication. If you know an entrepreneur who doesn’t have an attorney, be worried for them. If you own a business, you damn well better make sure your practices and your documents are legally sound. I don’t need legal services every month, but when I do, I have emails and phone calls with my attorney that have to happen. Sometimes it’s a ten minute back and forth email conversation, and other times it’s 45 minutes on the phone to straighten something out. Depending on the industry and what stage of the business someone is, this could be a more time-intensive part of the job. But it is definitely part of the job to some degree.

Constantly Evaluating Everything. A huge part of being an entrepreneur in my book (which, as you can imagine, is a very long book) is regularly assessing how things are working. Pricing, systems, client communication templates, hiring, training programs, etc. I consider this to fall under my Big Picture Duties, as what I’m really asking is “Is this part of the business working?” I feel pretty confident saying every entrepreneur does some version of this. So if you look at the business owner in your life and they seem to be mindlessly scrolling through something on their screen, sure, they might be. But they might also be looking numbers, feedback or reviews and deciding if they need to adjust some part of their company to make it better.

Should I change our studio space? Does this payment schedule still make sense? Should I get a chrome silver manicure?

Revising Everything. Okay, so hopefully not all at once. But that constant evaluation often means something (or many things) need to change. And changes don’t happen on their own! There are simple changes like changing over from a personal to a business Instagram account. And there are bigger changes, like website makeovers, switching to a new client management system or setting up new accounting software, that can take hours and hours and hours. The bigger the company, the less likely it is that the business owner will have to personally execute the changes, but solo owners with no admin staff are likely taking it all on.

So if you ask your entrepreneur friend what they are doing this weekend and they say “Working,” but you know they have no clients or their store/restaurants/studio isn’t open, keep in mind that they might be doing some (or all) of the things I mentioned, plus some I forgot or never thought of. And if you’re my friend or relative and you’ve secretly been thinking “What does she do when she says she is working in Charleston? I know she didn’t even bring her pro kit there this year!,” now you know.

If you have any misconceptions about your job or industry that you want to clear up, leave ’em in the comments. I love hearing about other people’s jobs because it helps me understand what their life is like. And understanding is key in any type of personal or business relationship, right? (Next up, my post about my life as an Amateur Psychologist.)

Have a beautiful day 🙂

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