I have a friend who’s a contractor. He does home improvements and things like that. He mostly works by himself, sometimes with a helper or two.

Recently, he was really struggling with his business and he came to talk to me. The business just wasn’t working. He was stressed out and miserable, barely making any money. The worst part is that he was doing the work—long hours, every day of the week—why wasn’t it working? He’s been in business for years and stays busy, why wasn’t it stabilizing? Why wasn’t it working out?

As we talked, the problem became apparent. He was working in the business, but he was never working on the business.

Writers are prone to the exact same mistake.

My friend loves to do the work of his trade. He’s good at it. He’s not lazy, and he has no problem showing up. As his business’s chief employee, he was doing all of the work that the company is supposed to provide. He’s doing roofs, building decks, remodeling bathrooms—it’s getting done.

The problem is that when you own a business as a solo-entrepreneur, you’re not just the chief service provider. You’re also the CEO, CFO, CTO, customer service, accounts payable, marketing, and quality control.

If you have employees, those employees show up and do the job you trained them to do until you tell them to do something different. In a bigger business, there are people whose whole job is to look at the company from the top and make system and structural improvements. For a big construction company, there’s a guy sitting in an office somewhere who has maybe never touched a hammer in his life, but he knows how to run the business and make the pieces all work together.

My friend was really good at putting on the tool belt and doing the work of the business. But all of those other business owner roles were being neglected. He was never working on the business.

If he was misquoting some particular type of job, he’d continue to misquote it. If he was messing up the scheduling in some particular way, he’d continue to do that. “I’m doing the work, I’m showing up, but nothing ever changes!” Exactly. Because no one’s there to change it.

I’m not picking on my friend. His experience is not unique to him, and I would wager that it’s a primary reason that small service providers and independent contractors fail. For what it’s worth, for some reason I have a lot of contractor friends, and I would wager that most of them have the same struggle.

According to U.S. Bank, 82% of small businesses fail due to cash flow management issues. For many of these businesses, there’s just nobody doing that job.

It’s not unique to the trades, either.

It’s a writer problem, too

Writers struggle with this same issue. Only with writers it’s a little bit more complex.

Writers have to work in the business. As a writer, you own a small business. That business produces content—books, podcasts, videos, whatever.

Writers also have to work on the business. Your business requires much of the same management as a construction company—marketing, systems, financial, IT support…just to name a few.

What’s interesting about writers is that some writers struggle to work in the business, while others struggle to work on the business.

There are some writers who have no trouble getting their butt in the seat and producing content. But they neglect all of the other issues that will actually get their work into the hands of readers and viewers.

There are other writers who love the idea of being a writer. They love to think about marketing strategy, book releases, business structure, and they love to have the best tools and software. But they really struggle to actually sit down and produce content.

Which camp do you fall into? Do you have to force yourself to produce content? Or do you have to force yourself to take care of the business side of things?

Traditional publishing doesn’t save you from having to work on the business. You still need to do all of these things—just ask any traditionally published author. No one gets a pass until you’re making enough money to hire other people to do these things for you.

Nobody wanted to take this picture, but they have to. Because they’re your employees and they’d really like to pay their mortgages this month. #bosslife

Everyone takes more naturally to one side of the equation than the other. Personally, I find it a lot easier to work on the business. That’s part of what makes me a great consultant. I love coming into a situation where I can do all of the thought work and development, but somebody else will actually create the content.

I typically have to force myself into the content creation side of things. Don’t get me wrong, I love to write. Once I’m doing it, it’s great. But I have to make myself get started.

If you love to work in the business

If you love to do the work of your business—creating content—then it’s important to specifically set aside time to work on the business. It won’t happen all by itself, and your great writing will never reach its audience if you don’t do that part of the work.

You might object, “But I don’t know what to do.” Fair enough. A big piece of working on the business is learning. If you set aside some time each week for this work, spend that time learning what to do…and then once you know, do it. Then come back and learn some more.

A great place to start is The Company’s Arche Year program. You can take it as part of a Cohort with other writers who are in your same position. Or the videos are available on-demand to all members and you can watch the specific topics you want to grow in.

Working on the business includes:

  • Marketing/Platform Building (Website, social media, events, newsletter, lead magnets)
  • Improving your distribution systems (Are you producing content that’s not getting to the audience? What’s the choke point?)
  • Maximizing revenue (how you can you diversify and maximize revenue off of existing content)
  • Developing helpful relationships (outsourcing, networking)
  • Taxes and small business administration
  • Improving yourself as a business person and leader

…and so much more!

Don’t be overwhelmed. Just set aside time and do one thing at a time. If you do anything that’s on mission, it will move you towards your goals.

If you love to work on the business

You’re in good company!

Check out this article on developing a sustainable writing routine here.

You probably know exactly what you need to do. Set aside time, protect it, and ruthlessly eliminate distractions.

This is the one area where you can’t be replaced! Ironically, we can hire somebody to work on the business for us (mostly). We can hire website designers, marketing experts, and accountants. But your business can’t hire a different writer!

Know Thyself

Everyone has a natural bent one way or the other. If you’re not reaching your goals, could this be part of the reason why? Are you neglecting half of the duties of your chosen profession?

In order to be successful as a writer, you have to do it all. The only way out is to hire people to do things for you. You may be in a position now where you can hire someone to do the least desirable tasks. Hopefully, as you work, you’ll be able to outsource more and more.

The important thing today is to recognize the gaps in your operation, and begin to exercise discipline to fill them. That’s the way your business grows.

Are you a writer? Tell me below, are you more prone to work in the business or on the business? Have you found anything that helps you cover the other side?


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