Being a solopreneur is awesome — freelancing in particular.

You control what days you work. You set your own hours. You can wear whatever clothes (or lack thereof) you want. There’s no commute. You decide what work to take on and reject. You can sneak a snack or cat nap whenever you please (well, mostly). You can take days off when you want or need to. And your boss is probably pretty chill. Right?

“Hell yes” to most of those things. And I’m no exception.

  • I choose to work a 4-day work week (have for about 10 years now).
  • My official business hours run from 5 a.m. – noon, so I get to enjoy the added daylight in the afternoons to run errands, garden, swim, hike, read, paint, or be utterly useless and binge-watch something on Netflix occasionally. Lady’s choice.
  • My work “uniform” varies from next to nothing in the dead heat of summer (be careful not to open your door for UPS or something — been there!) to winters full of plush pajama pants, warm cozy robes, fuzzy slippers, and arm warmers while I type.
  • My commute involves rolling out of bed and stumbling down a flight of stairs, with my office right at the bottom of them.
  • I’m super-fussy about who I work with and what kinds of projects I take on these days. If it doesn’t interest me, I can pass.
  • The kitchen is maybe 30 feet from my office, max. And I have a recliner in my office so I move a whopping 6 feet from desk to chair if I need a snooze.
  • I have 3-day weekends every week, but I still take other days off on a whim when I want to for day trips (I enjoy visiting creepy spots for photo trips) or even mental breaks. Just make sure you aren’t pushing up against a deadline.

And while I’d argue I have one of the best bosses around, when she’s not being a bit of a slave-driver, sometimes she can be a little too chill. That’s what I want to talk about today.

Freedom from Authority (& the Necessity of Discipline)

I’ll admit. Discipline doesn’t always come naturally to me. I’ve always been a bit of a rebel. I don’t much care for authority figures in traditional constructs, and I’ve probably been butting heads with them since I could walk. If you’re doing something stupid, I will tell you. If you’re making shit decisions, you’re going to hear about it (especially if they affect me). If your ego’s getting in the way of basic common sense, I will knock it down a peg or two. And if you tell me what to do, you better have a damn good reason for why I should.

That said, none of that is true because I’m trying to be an ass. If I stand up to authority, it’s for good reason, and usually for your benefit.

This applies to my clients as much as anyone. It’s a big part of why they hire me in the first place. People don’t come to me when they want a “yes man” type. They come to me when they have problems and they want actual solutions, even if those solutions mean listening to things they don’t want to hear.

More important, I don’t like dishonest people. I don’t like fake little schmucks who pretend to be something bigger or better than they are. I especially don’t like it when these people are in a position of authority over others, whether they’re a boss or they’ve put themselves in a position to teach or “help” those newer than them when they’re essentially frauds.

Standing up to authority figures has its downsides. But it can also be healthy, rewarding, an important part of exercising the kind of critical thinking you need to succeed in business.

But what happens when that person in authority is you?

What happens when the person bossing you around is the one who stares back at you in the mirror?

What happens when you’re the one in a position to make stupid decisions?

Or when you’re the one whose ego can get in the way?

Or when you’re the one who feels like a fraud?

It comes with the territory when you’re self-employed. One of the biggest risks you’ll face when you go into business for yourself is you.

Again, I’m no exception.

  • There are times I want to do something in my business even though I know I’d tell a client they’d be friggin’ crazy to make that choice in the same shoes.
  • There are times I push myself too hard. I almost quit early on because I burned myself out so badly I made myself physically sick for months.
  • There are times I don’t want to let an idea or project go even when it’s run its course because my ego just doesn’t want to admit I failed. (And FYI, “failure” is not a dirty word. You should learn to embrace it.)
  • There are times I wonder what the hell I was thinking to ever believe I could do this and succeed. I’m no stranger to impostor syndrome and finding myself full of doubt. That’s a little different than being an actual fraud like the insta-expert types, but it can lead to equally-stupid decisions.
Side note: What I often refer to as “insta-experts” would be folks such as the freelance writers with barely a year of experience sucking in even newer folks with courses they aren’t qualified to teach… or the little wretch of a self-professed marketing expert I came across last year who, along with her partner, had to rip off intellectual property from a major corporation like Kraft to come up with their own branding because they were lacking talent, competence, and ethics. (Can you tell I’m not a fan?) If you want to know more, you can listen to this episode of my freelance writing podcast featuring guest, Philippa Willitts (a follow-up episode on this topic is coming soon):

But despite those things, it’s not like I’m going to stage some rebellion against myself just because I’m the big bad authority figure in my own business. I’m not likely to put myself in my place and tell myself what I’m doing is dumb as hell even if it is.

It’s sometimes a bigger struggle to be honest with yourself than with anyone else.

Denial and complacency are easy. They’re also lazy. And they’ll ruin you if you let them.

That’s where discipline comes in.

When you’re your own boss, you have to be disciplined in the traditional sense. You have to meet client deadlines for example. You have to keep progressing toward your financial or other business goals. You have to get through a day’s tasks even if no one else is looking over your shoulder. You have to drag your ass out of bed every day even though there’s no HR person keeping track of how many times you played hooky. All of that takes discipline

But there’s an even more important part of being disciplined as a solopreneur.

You have to get shit done. But you also have to know your limits.

As much as you have to be able to stop yourself from totally slacking off, you also have to be able to stop yourself from pushing too hard. You have to be disciplined as a worker. But you also have to be disciplined (and realistic) as a boss.

With Great Power Comes…

Meh. You know how the rest of it goes.

When you work for yourself you have all of the perks and freedoms I talked about earlier. You also have the ability to become a bit of a tyrant. So what’s the key to balancing it all?

Be realistic. 

Yeah. It’s that simple.

You make the rules. You set your own terms. But when doing those things, you need to be realistic about what you’re capable of, what you can afford, and what you have the time and energy to do.

It’s okay to push yourself. I’m a big fan of that. The way I see it is this: If you reach every goal you set for yourself, you aren’t setting ambitious enough goals. You aren’t pushing yourself. This is why failure is important to growth.

That said, lofty goals shouldn’t be totally unrealistic ones.

Take freelance writers like me for example.

A writer in the U.S. could set a yearly income goal of $50,000. It’s realistic. With even basic business skills and a tiny bit of writing talent that’s not a tough goal to reach.

What about $100,000? For many that might sound like a stretch, but it’s still very realistic if you’re willing to put the work in.

Go into it expecting to make seven figures though? You’d be a hell of an exception (and in reality, you’d probably be making that through info products, courses, and other income streams — not actually freelancing for clients). For the vast majority of freelance writers, it’s not realistic.

When you set unrealistic goals, you put unrealistic expectations on yourself. 

That’s why it’s so important that when we set our own terms to fully embrace the joys of working for ourselves that we don’t lose our heads in the process. Going on a power trip or ego trip isn’t going to get you very far. Neither is slacking off because you don’t have the discipline to do what needs to be done.

So enjoy those good things — the pots of fresh coffee all to yourself, the “office pajamas,” the fuzzy slippers, the hours that suit your natural schedule, the income potential, freedom from a watchful eye, and the ability to make your own choices about decisions big and small. But choose wisely. You won’t always get a second chance.

Has discipline ever been an issue for you working from home? Has the authority of being your own boss ever gone to your head? How do you control the urges to either not get things done or to over-work yourself? Leave me a comment. I’d love to hear about your experience.

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