Why You Should Fire Yourself

Illustration of Man Looking into Mirror

What would you do if you discovered that the secret to your success online lay in firing yourself? Would you do it?

That’s the question Alex, a freelance copywriter, had to face.

Alex started his copywriting business three years ago, after the local newspaper he worked for as a staff writer was shut down.

From the get-go he scrambled to pick up writing jobs, tapping his network, searching freelance websites, and sending query after query.

Opportunities soon began to open up for him, and he took every single one.

Let’s take a look at the specifics of his story …

What’s the true cost of flying solo?

Alex wrote magazine pieces, blog posts, ad copy, web content, press releases, menus, brochures, instruction manuals. You name it, he wrote it.

His clients were businesses and solopreneurs of all types and sizes. Little start-ups, a big bank, neighborhood shops, a medical clinic, a solar power plant on the other side of the world.

With his take-any-client-with-a-pulse approach, he managed to keep the work flowing for the next three years.

In fact, many times it flowed too heavily, and he would log long hours, day in and day out.

Falling out of love with your business

The concept of a weekend soon became a distant memory.

Alex eventually got worn out and fell out of love with writing. At that point a mutual acquaintance suggested that he give me a ring.

A few weeks later Alex squeezed in a call with me while on the road. He said he wanted to start enjoying his work again, which probably required working less and somehow making more money.

After he gave me the rundown of his business, I told him he could easily have what he wanted, but he needed to step back for a few days to develop a business plan, decide on some goals and objectives, and map out a few specific strategies.

He told me he didn’t have the time for that.

He was running his feet off trying to keep up with everything on his plate.

Why you should fire yourself

“Alex,” I said, “if you sincerely want to work less and make more money you should consider firing yourself.”

I heard a long pause on the other end of the line, before, “Uh … what exactly do you mean by that?”

I told him …

There are two essential ways a small business owner works — in their business or on their business.

Working in the business means doing all the day-to-day stuff, such as servicing clients.

Working on the business means stepping away from the daily grind to do some planning and strategic thinking.

The trap of being a small business owner

Most small business owners get caught up in working in their business all the time, and never working on their business.

It’s a trap, because without planning and strategic decision-making, the business can suffer, and so can the owner. In his case, Alex had hit a revenue ceiling and an emotional low at the same time.

For many, the trap is hard to get out of because, if they’re on their own, it’s up to them to do all the servicing. They feel they can’t stop, but if they don’t stop, nothing will ever improve.

High-level creative thinking for efficiency

I told Alex I saw so many ways for him to improve.

  • He barely had any clients in the same industry
  • He was doing every kind of writing under the moon

Both of those things had made him woefully inefficient. If he specialized in some industries, and if he concentrated on his higher-value services, like content development, instead of getting bogged down in things like product descriptions, he could easily make more money in less time.

But figuring out what industries to target and how to transition out of low-paying work would require some high-level creative thinking.

And you can’t just do that when you’re caught in the daily grind, worrying about all the work you have to do for your clients.

Hire yourself as CEO to save your business

You have to totally get away from the day-to-day stuff — in every way, including emotionally. You can’t have any worries about the business.

You have to think about it objectively. After all, the right way forward might mean dropping a client you really like.

You’re not going to do that if you’re in the headspace of the guy involved with the client.

“So,” I said to Alex, “fire yourself as the copywriter and hire yourself as CEO.”

He wanted to know who was going to do all the work. “Nobody,” I said. “But you, the copywriter, don’t have to worry about that. You’re out of a job. Let the CEO worry about that.”

Another pause. “I’m pretty sure the CEO would be worried.”

I agree. But give him a chance to figure out solutions. He won’t, however, just think about how to get the business through the next week.

As CEO, he’s going to do some long-term planning. And he might make some hard decisions. One of them might be what to do with the copywriter he’d just let go.

But I imagine he’ll think you’re doing a pretty good job. So he’ll probably hire you back, with perhaps the insistence you get some work-life balance going.

Alex said the idea had some appeal to him, but he was seriously worried about finding the time and the emotional distance.

I suggested he do what he could to make the time, even if it meant turning down a little work. It might be hard, but the CEO in him would understand.

How to refocus your business and regain your sanity

Alex would eventually follow my advice. He booked himself a weekend getaway at a cottage, took a business planning kit with him, and worked all weekend as CEO.

One of the decisions he made was to focus on the healthcare industry. Both his parents were medical professionals and he had a personal interest in health, enjoyed the work, and felt it was a growing industry.

He also made a hard decision to stop taking certain types of work, as well as any work below a certain pay rate.

Oh, and he decided to hire himself back as the copywriter.

Alex would stick to his CEO’s decisions, though he often had to fight the fear that turning down work was a bad thing.

His persistence would pay off, though. Two years later he became an established, high-paid writer in the healthcare industry.

For the most part, he stopped working crazy hours and he was much happier.

The big takeaway

If you’re not finding the success you seek, try temporarily firing yourself as your business’s service provider, and hiring yourself as its CEO.

Make sure to think completely objectively about your business, and be prepared to make hard decisions. Push yourself to think creatively and strategically.

You’ll probably find being CEO fun and rewarding. You get to be the big shot, for a little while at least, before you head back to the grindstone.

A good rule of thumb is to fire yourself for a day or two every quarter.

Going on a retreat, like Alex did, is a good idea. And you don’t have to do all the planning alone. Consulting a business-minded friend or working with a professional can be well worth it.

Author’s note: this post is based on a business owner I’ve coached. I’ve changed his name and any telling details.

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Reader Comments (69)

  1. says

    Couldn’t agree more. I think independent consultants of every flavor run into this issue at multiple points in their careers. There’s a lot of work, sure, but it’s not the kind of work you’d like to be doing. Stepping back, taking a few days off, and re-assessing your approach can go a long way toward better work-life balance and– in the long run– a more profitable business.

    • says

      Adam, great point about work-life balance letting you run a more profitable business. Working less but making more money is counter intuitive, but true if you work smarter.

    • says

      Seriously! One of the first things I did when I started reaching the point of no return with my business was reach out to other people who used to be in my shoes. Talking to other freelancers and freelancers-turned-CEOs really helped me to make the choice to take a step back from what I was doing.

      One of the best things you can do for your business is consult with other successful business owners. You’d be surprised how many people out there will be willing to help you if you’re open and honest with them.

  2. says

    Today I commit to firing myself for a couple of days each quarter! I know I want to focus on writing white papers for tech companies but I haven’t taken the time to plan how I’m going to get there from where I am (writing most things that come my way).

    • says


      Love the commitment. May I suggest a book that might REALLY help you? It’s a quick 92 page read… I read it on the plane on an east-coast to west-coast trip. REALLY got me thinking, especially the chapter on SPECIALIZATION (which is what it seems you want to do). It’s called Built To Sell. You can get it on Amazon, but may be able to get a better deal on it by going to BuiltToSell.com.

  3. Christian says

    THANK YOU for this article. I just fired myself. (If I hadn’t, I might have killed myself instead.)

      • says

        Make that two! This was a great read at the perfect time. Thank you!
        (p.s. how often after you fire yourself, do you find yourself taking the step to hire people who are better at something than you are, or even just to get things done? Would love some guidance on that happy medium if you have some to share.)

        • says

          Great question, Bonnie

          From what I’ve seen, the best hiring decisions are made after doing some serious planning. You want to have clear answers on what the role is? How is it going to contribute to your goals?

          One typical approach that I see frequently is the original owner moving into more of a consultant role, helping clients at the strategic level, and leaving some (or all) of the execution of the work to someone else. Of course, if you’re hiring for this role, it would be great if you can find someone who is better at the service work than you. Not always easy, but if you focus on getting the right fit, it can do wonders for your business.

          Another typical approach is to hire someone who can free you up to focus on sales and service delivery, so that hire is more of an assistant.

          A lot of business owners do their hiring in a reactive way — after they’ve been run off their feet trying to do it all themselves. Being proactive is best – but you have to have confidence that your business can support a hire – which gets us back to how important it is to get away and do the planning.

  4. says

    Great article! I totally needed to be told this today. I’ve been swamped the last few weeks with client work and although I have been doing a ton of planning, I haven’t made the time to implement my planning. So I need to “fire” myself for a little bit and take time to plan for real. I’m actually moving next weekend, so maybe I’ll “fire” myself from Friday to Monday and give myself a few days to unpack and do some CEO planning.

  5. Anita says

    Such a great post! Thank you. As a very new (very very new) self employed person I needed to read this. Thinking long term is crucial to my success rather than just focusing on next months rent!

  6. says

    Oh, how WELL I can relate to this post, Donald. I’ve been thinking about it as firing clients that aren’t a good fit, but not as firing myself. What a concept! Gotta go have a chat with that woman in the mirror.

  7. Victoria Ipri says

    Hey gang…great article, Donald. I’ve fired myself more times than I can count, but the CEO is a slave driver and I end up as CEG again (Chief Executive Grunt).

    Seriously, excellent reminders about stepping away for what one of my colleagues calls “thinking, planning, scheming time.”

    Now if I could just finish everything on my list for today, I might be able to sneak out early.

  8. says

    Hi Donald,

    Thank you so much for writing this post! I hope to read more posts like it.

    I can relate to Alex on many levels and will fire myself today as a freelance writer and hire myself as a CEO. Like Alex, I write for a few industries and provide various writing services. But, I find find myself drawn to creative writing in addition to ghost writing and content writing. Perhaps, I should focus on these areas. I won’t know for sure until I too work all weekend as CEO.

  9. says

    As a small business owner this post really reminds me of my business beginnings and sometimes I have to fire myself to rework my plans. Thanks for reminding me to plan!

  10. says

    Great article. If this story resonated with you at all, I strongly recommend that you read The E-Myth Revisited, by Michael E. Gerber. This book explores the concept of “working at” and “working on” in a fabulous and easy to read way.
    Have a business plan!

  11. says

    Great points in this article. I agree – taking a step back and focusing your efforts in a strategic direction (even if it means turing down work) is going to be more profitable in the long run. From a marketing standpoint, it also gives you a direction to focus your efforts, resources and marketing message.

  12. says

    Great tips! It’s so easy to fall in the trap of working only “in” the business and not “on” the business. Thanks for the reminder and advice!

  13. says

    Okay, now I feel like an idiot, Donald. I’ve preached this many times to CEOs and COOs as a business consultant, and although I already knew it to be the case, your post made me admit to myself that I wasn’t following my own advice. I did make a half-assed effort a little over a year ago, but didn’t give it the follow-through it deserved.
    I think it’s time to have a tough talk with myself and part ways. I hate letting me go, but it’s the best thing for the company.
    Thanks for the wake-up call.

  14. says

    I couldn’t agree more. Great stuff. Have a break then focus on more important things then you can think better and plan better.

  15. says

    Wow, this article really hit home. I have struggled with this. Sometimes I think I’m afraid of what I might see if i’m completely objectively with my own business! Thanks for the great points.

    • says

      Ariana… that’s a really insightful point…. I often find that if I’m not making the effort to step back and do some planning — whether that’s for work or life — it’s because I secretly know there’s a problem, one that I’m afraid to deal with.

  16. says

    I often skim articles for the good meat but I read this one very thoroughly. Great, great advice. I need to definitely step into my CEO shoes for a switch. Thanks so much for the challenge.

  17. says

    Read the post its just fantastic and the catchy title “Why you should fire yourself” is awesome for this post…liked it!

  18. says

    I agree with firing one’s self, to have an overview of what the business require to be more effective and beneficial.
    Working without plan is like walking in a library without knowing what book you are looking for.
    Strategy and planning is the base and bedrock of every business, (to-do) what ever small or large.
    Copyblogger changed my life.

  19. says

    Great post Donald, It a very interesting topic that you brought in today.
    I totally agree that when we start as a self-employed person we often tend to get into situations(especially if we just got of a company).
    When in a company you don’t have to worry about other people’s work unless your work depends on them but when you are the sole hero of your ship you need to do all the work which will leave you overwhelmed.
    The idea of confining yourself to find the leader in you will always help you know what you wanna do in future and most importantly HOW to do it properly?
    and yes, you can always go back and be that that slogging employee with no goal only if you love it that way 😉

    • says

      Robin, thanks for adding in the comparison to working at a company, where the CEO role is filled by someone else. That’s a helpful framing for anyone who’s recently moved from employment to self-employment.

  20. says

    Recently I did the opposite. I hired myself….twice.
    A few months ago I was struggling with letting myself work on the business. So I hired myself for 20 hours a month.
    It’s purely a psychological tactic but it worked. I had to work more but I got to do more of what I liked. And I focused more because I had to. Once I got over the work hurdle I was happier.
    My next issue is I always felt guilty about taking time off. All it would do was put me behind on my schedule.
    So I hired myself for time off. This time I hired myself for the equivalent of weekends off.
    Again, it’s put more pressure on me with the extra work, and my last few weeks were quite stressful.
    I’m now in the position that I’m ahead on my work and l currently have 2 days holiday accrued.
    Now my problem is working out what to do on a day off!

  21. says

    This is great insight. I’ve never met anyone who regretted stepping away from the day to day be strategic. The headline is great too. Very eye catching and it drew me in – instantly.

  22. says

    You have to consider the big picture every once in awhile. It’s easy to get bogged down in the details. It’s important to consider the best ways to make dependable money for the long run. For instance, that might mean pursuing more recurring income. Great post!

  23. says

    Nice article,

    I have actively made the change this week to do just this.

    Far better to make 20% margin by using freelancers, NOT doing the work and growing business rather than 100% but not being able to grow the business.

  24. says

    This is a superb article and it does resonate with me right now! I am a bit at a crossroad and feel I should take a step back and re-think a proper strategy! Whilst I am happy to write about pretty much every topic under the sun, I’d like to become an expert– and indeed a CEO– of my business.

    I don’t think I am a born-Onassis lol, but I do know the rules and I most definitely should be taking steps and maybe….fire myself…for a few days and come back as a completely new ME! ::)

    There is a lot of psychology behind these kind of choices and I guess it’s the first step that’s hard to take…or sometimes, the burn-out happens and you have no choice but clear your desk, start afresh with brand new objectives, goals, expectations!

    This article has definitely given me a BOOST! Ok, off thinking about how to change things for me so that I get much more out of myself!




    • says

      Hi Yoan, you nailed the crux of this post …. that the challenge is to play the CEO role for your business before you get burned out… good luck on your transformation to a new you!

  25. says

    Something to try – not easy when you feel you’re not doing enough all the time. But I am intrigue by Tiggerito’s approach.

  26. says

    What you said about small business owners being consumed working on their business is true, but is essential for small businesses who do not have sufficient capital to start small and work solo, so soon as the business pick up, it is time to expand the business, by hiring people and assigning duties and responsibilities to them. Now the former solo-prenure can fire his/herself and do the executive work of planning and making important decisions about the former small business now becoming a cooperation.

    If a small business without huge capital starts off hiring people, the financial drain on the business may suffocate the business and it may never see the light of the following day.

    • Carolin Geissler says

      Nina, while you’re right, Donald wasn’t saying you have to actually hire someone else. His point is that as a freelancer and a solo-entrepreneur, you have to do more than just one job. Alex in this example was only doing the writing part, he wasn’t thinking about the business part of it all. So it’s a metaphor or a simile, so to speak, to take a step back and look at your business as if you were the CEO and analyze it accordingly.

  27. Carolin Geissler says

    Donald, very interesting way of putting it!
    One of the best pieces of advice I’ve ever received was to set an imaginary hourly rate you don’t want to go below. Whenever there’s a new job, look at how long it’d take you and how much money you’d make. If it ends up below your hourly rate, really make sure to think about what it is about this job that justifies taking it even when it’s not ‘worth’ it (e.g. it’ll look good as a reference if you’re starting out, it’s in an area you want to break into, you’re in need of money because you’re saving up for something, etc.). If, like Alex, you don’t have trouble finding jobs (or, like me, you have a part-time job that pays the actual bills), you can afford to turn down jobs that will simply not be worth your time.

    • says

      Well said, Carolin… as you’ve illustrated it’s important to be strategic about why you take on certain jobs. The challenge, of course, is to not rationalize a poor decision :)

  28. says

    This definitely hits home. I have been giving myself at least an hour a day lately to actually work on my business, and it’s made a world of difference. The first thing I did was figure out which clients were least profitable based on rates, referrals, etc. Once I fire myself from working with them, I will have even more time to dedicated to building a better business. :)

    • says

      Hi Kristi, so glad to hear that you’ve set aside time to work on your business – and that you’ve seen the difference already. BTW – I like your process of evaluating clients – and including their value to you based on referrals.

  29. says

    Great article, Mr. Cowper. The timing for me, like others here, was perfect.

    Just started using FreshBooks to more effectively manage our business, and it’s given me a chance to reexamine the “IN” and “ON” of which you wrote.

    Thank you, sir!

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