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So You Wanna Work in Your Bathrobe: Five Survival Tips for Small-Scale Entrepreneurs

I got called an entrepreneur today.

It startled me.

The family with the most amazing pho restaurant in the world (Viva, for those interested) is an entrepreneur. My friend Andrea, who runs a kick-ass design firm with several employees, is an entrepreneur. My friend Dave, who bought a food truck and then opened a kickboxing gym, is an entrepreneur.

I just write articles and novels, often while I’m sitting on the couch in my bathrobe. Or lately, in my amazing Sarah McLachlan hoodie (thanks, Sarah!).

It’s pretty amazing that I get paid to write for a living, but I don’t think of myself as a business. Is writing a business? Sure. Is journalism a business? Sure.

But I have no storefront, no negative reviews to deal with (yet), no unhappy customers, no silverware stealing-employees, no long meetings with people in suits (thank god! I’ve spent enough of my time in those).

So I never think of myself as an entrepreneur. Entrepreneurs are people who have to hustle all day, negotiating and making deals, while I can do a good day’s work in four hours and then take a nap if it suits me.

Getting called an entrepreneur made me wonder if the way we think of business is changing. When I started my life as a freelancer, I got asked when I planned on getting a real job. Now the first thing people tend to say is, “You work for yourself? Cool! How do you do that?”

Here are my five secrets to being a successful small-scale entrepreneur:

1) Get Clear About What It Is You Have To Offer: I’m a writer, but you may have noticed there’s about, oh, five billion of us out there. So how did I figure out what makes me different? I listened to my clients, even in the beginning when I only had one. I’m a fast writer, an accurate writer, and a reliable writer. I’m good at putting people at ease, and getting even seemingly boring people to say interesting things. Apparently that sets me apart without even getting into specialization, which I’ve only started to dive into.

Maybe you also do something a lot of other people do. Figure out what it is about you–your process, your approach, a certain skill set–that makes you stand out from the pack. And then market the hell out of it (and by market, I do not mean spamming all your followers on Twitter and Facebook. That is not marketing. That is annoying. Two different things.)

2) Sometimes, You Have to Hustle: People who look at my life with envy often don’t realize what it took to get here. Three-hour breakfasts? Naps in the afternoon when required? Sure. But I wasn’t doing so much of that in my early twenties while I was building my client list. And even when it seems like I’m taking it easy, I always have my eye on the months to come. If those months seem slow, you better believe I’m getting in touch with my clients and letting them know I’m available. Will they contact me if they need me? Probably, but I still put myself out there. It never hurts to remind people that you’re alive and willing to work, as long as “reminding” doesn’t turn into “stalking.” Companies don’t tend to hire freelancers who stalk them.

3) Get Comfortable With the Unpredictable: Here’s two other things that are said to me a lot: “You’re up early,” or “You’re up late.” When you’re your own boss, there are no set hours. You work when there’s work. You’re probably going to work through a lot of weekends and evenings, even long weekends. How else are you going to make up for those random Thursday afternoons when you decide it’s a good time to go Christmas shopping? It balances out.

Another note about unpredictability: I don’t suggest going into business for yourself without savings. You will have busy times and lean times, and lean times are awesome for long-range planning, focusing on smaller-but-still-important projects, and cleaning that house. If you have savings, you don’t have to waste those precious lulls by worrying over how you’re going to pay the mortgage. (You probably will still worry, just not as much. And that leads me to…)

4) Accept That Worrying Is Normal: If you’ve worked for a large corporation, you probably had a stressed-out boss. I had several. These creatures run around from meeting to meeting, usually in an ill-fitting suit, arriving early and staying late. They often grab lunch at their desks, and if they do stop to chat for a moment, they’re usually looking uneasily over their shoulder, as if at any moment some huge mountain lion is going to pounce.

Being an employee can be stressful too. But the closest you will ever get to understanding a CEO is working for yourself. All those things your boss worried about? They’re now your responsibility. Maybe you don’t have a board or an accounting department, but the day-to-day stuff? How to pay that bill, how to expand the business, how in the hell do I pay GST? Yep, that’s all on you now. So a little worrying is normal. Just use it to spur you into action (see point number two).

5)  Be Grateful: It’s human nature to dwell on what we don’t have. When you work for yourself, you won’t have those nice, seemingly free benefits (you did know you were actually paying for those, right?). You may not have people stopping by your office to ask about your weekend. You won’t have a regime, or schedules, or someone to keep you on track–unless you build those systems for yourself. You won’t have a pay check that arrives like clockwork every two weeks (unless you’re really, really lucky. I’m still waiting to get paid for work I did in August. In AUGUST!)

But if you obsess over that stuff, the best thing you can do is get another job in an office. Because you’re missing the point. And the point is all the things you do have, and number one is Freedom. Creative freedom, personal freedom, the freedom to set your own hours and turn down projects that don’t interest you. And freedom is priceless. Do you know how many cubicle drones would kill for freedom? So miss your old co-workers for a minute and then shut the fuck up. Cause you can always meet them for lunch. And then go have a nap while they drag themselves back to the office for yet another meeting.

Do you work for yourself? What helps you be successful? Please share your tips in the comment section. Or, conversely, would you ever work for yourself? What stops you?

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  1. Samantha Dunaway Bryant

    I am fitting my writing around a day job because I don’t have much savings and can’t handle the unpredictability of income. Good post that reminds people to be realistic about their expectations for income–especially at the beginning!

    It used to be that “being a writer” was my daydream. Now I am a writer, so I daydream about being *only* a writer.

    • J.H. Moncrieff

      I hear you, Samantha. I did that for a long time, and really still do, because although I’m a full-time writer, a lot of it is journalism articles to pay the bills.

      We have the same dream! Let’s cheer each other on.

      Thanks for reading, and for commenting.

  2. Dean K Miller

    Interesting to read this. I am mapping out my writing world persona currently, working at nailing down my specialty. Day jobber still (and with good reason) but that all changes in the not to distant future. Thanks for this, J.H.

    • J.H. Moncrieff

      Welcome to my blog, Dean! Thanks so much for taking the time to leave a comment–it is appreciated.

      Good luck with taking the plunge in the near future. Exciting times are ahead for you, and I’m glad this post could help.

      If you have any questions once you’re on your own, feel free to shoot me an email. Always happy to help.

  3. Susan Scott

    Thanks J.H. Great post. Life is for me a constant juggle, work at my husband’s rooms, blogging (not as frequently as I would like), WIP – this last especially time consuming.
    I guess it boils down to setting one’s priorities and making time for a ph call to a friend, a quick meet for a cup of coffee, a walk and time to smell the roses ..

    • J.H. Moncrieff

      Thanks, Susan, and thanks for commenting. I have a hard time juggling everything as well. Time management is definitely crucial, whether you’re working for yourself or someone else. Haven’t mastered it yet.

      Hope you find the time for that phone call. Life is short. <3

  4. Steven

    Great tips! Most people don’t realize that working for yourself involves sacrifice and some serious guts. Too many people are used to just showing up at working, clocking in, “working” and then clocking out. For entrepreneurs, the work never ends.

    • J.H. Moncrieff

      True enough! Thanks for your comment, Steven. Funny how we both wrote about this topic around the same time. Great minds think alike. 🙂


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