How to Smash Your To Do List When You’re Your Own Boss

An insidious curse haunts all business owners and it doesn’t matter what business model they use or how large or small their company might be. The curse is freedom.

You’d think freedom was a blessing, and it is. It’s the ultimate goal of the successful entrepreneur. They want to enjoy freedom from someone else’s schedule, from corporate bureaucracy and from some lame manager’s to do list. They have the freedom to do work that counts, to blow off on a Tuesday afternoon to spend time with family, or to play by day and work at night.

All entrepreneurs chase freedom. We have our personal reasons to want it, but we share the same goal.

But freedom comes at a price. The curse kicks in and the universe demands payback for the gift we’ve created for ourselves.

Freedom is a curse precisely because it’s freedom. Freedom runs away from structure and hides in the bushes while discipline marches by. Freedom rejects fixed schedules and doesn’t answer when your inner deadline bailiff calls.

Yet if you’re an entrepreneur, you need structure, schedules and organization. It takes discipline to build the kind of business that allows you to blow off afternoons or take month-long holidays without the house of cards tumbling down.

You won’t stay your own boss for long if you don’t harness discipline in your life and business.

How to harness discipline and ride it hard

Trust me, I’m the last person to suggest you adopt discipline as a permanent state of mind. Discipline and I have a tenacious relationship at best. I hold on because she’s valuable to me; she barely concedes to put up with me. (Yes, discipline is a she. I have no idea why. Freud might).

Discipline isn’t some unseen cosmic force. Months of meditation aren’t required. No one is disciplined all the time, but being able to switch it on at the times we need it is the skill that forges business empires. It’s just a state of mind we enter and leave at will, just like any other state: feeling happy, being sad, and so forth. Here are three techniques that focus on cultivating a state of discipline that I’ve road-tested often with clients, with fantastic results.

Set micro goals

You need to set micro goals. Most entrepreneurs figure out that a long-term game plan, a vision board and clear goals are crucial to big-time business success. Yay for The Secret!

But many business owners don’t have itty-bitty sized goals that keep them on the straight-and-narrow of productivity performance. This habit is crucial. Long-term goals are great since they get us fired up and inspired. Actually doing stuff on a daily basis, however, comes down to how you tick off tasks.

The whole point of discipline, for entrepreneurs at least, is to move your business goals forward, bit by bit, each day. It ‘s about incrementally building your business, spooling up your momentum and eventually charging down the freeway of big profits, impact and perhaps fame.

The key is in the daily “micro-push”.  You must learn the discipline to add to that momentum on a daily basis, or you very quickly lose any acceleration you have.

Setting micro goals is about translating your long term vision for success into a weekly or, better yet, daily game-plan for winning big in business.

The best productivity system I’ve ever used revolves around the simple concept of writing a maximum of three goals on a single Post-It note. You’re allowed a single Post-It per day. You make it your day’s focus to, above all else, absolutely nail those three goals. If the goals are too big to achieve in a single day, you’re forced to split them into mini goals that can be achieved.

Realistic expectations

The reason the itty-bitty goal system works so well is simple. Setting a maximum of three tasks per day manages expectations. Achieving three tasks is easy. You could probably nail five, if you really tried, but that isn’t the point.

When you set realistic expectations and achieve them, you build a habit of success. You also build a habit of discipline. You’re conditioning yourself to, if all else fails, nail three important tasks per day. That builds crucial momentum.

A lot of entrepreneurs have unrealistic expectations. As a group, entrepreneurs tend to be a fairly cocky bunch. They do have reason for being this way: entrepreneurs are awesome. They achieve huge things. Nevertheless, most entrepreneurs have an unfortunate habit of setting stupid-big expectations for their own productivity.

If you have a to do list with hundreds of items on it, you ‘ll never tick them all off in a day, week or even a month. Even if you were nailing twenty tasks a day, to do lists have a habit of spawning more and more items.

The other sucky thing about unrealistic expectations is that you never meet them. You fail to achieve your performance target, which means most entrepreneurs end up feeling shitty about themselves and their performance.

Realistic expectations, like the “three tasks a day” strategy, give you the chance to win some personal success and, crucially, to pat yourself on the back for doing a good job. Success breeds success. Ticking off your three tasks on Monday (and celebrating) is far more likely to lead to the same level of discipline on Tuesday!

Discipline also applies to breaks

Celebrating your discipline, and the success it creates, is key. To adopt a habit of discipline, you need to convince your unconscious mind that it’s worth it  – that there’s something positive to be gained from it all. This means rewarding yourself for a (three task) job well done, rather than beating yourself up over your endless to do list.

Build a habit of small, incremental successes and simultaneously build a habit of celebrating that success. Be disciplined about patting yourself on the back for ticking off your tasks. Be disciplined about taking breaks too.

In most western countries, a minimum of a half-hour break per eight hours work is a mandatory, legislated requirement. For once the government got it right! What is it about entrepreneurs that makes them think they ‘re above taking breaks?

It comes back to cockiness and the belief that you can do anything. Get real. You can’t. You are not Superman.

Working for ten hours straight dramatically affects the quality of your work. If you think you ‘re capable of producing game-changing business ideas and insights while burning the midnight oil, you’re dreaming.

While you are conditioning yourself to be disciplined with work habits, create the same discipline around your breaks and down time. This is the best way — trust me. The alternative means burning out and falling to pieces or, more likely, having your unconscious mind self sabotage your efforts at discipline from the get-go.

Putting it into action

The key to mastering discipline, of course, is to actually do something. Don’t convince yourself that this needs to be some kind of cathartic, transformational, life changing experience where you cry, sweat and bleed. Don ‘t start on a milestone, like next Monday or on New Year’s Day.

Start now. Start gradually, without ceremony or worry. It ‘s as easy as writing three tasks on a Post-It. Discipline can be yours.

So, what do you want to achieve today?

Peter Shallard is the Shrink for Entrepreneurs. He helps business owners figure out how to achieve wealth, freedom AND sanity… all at the same time! Check out his Business Psychology Blog or get fast tips on overcoming entrepreneurial obstacles in his free ebook.


  1. Anthony on the 13th September

    Thanks for a very insightful post!

    I wrote myself a to-do list a couple of weeks ago which ended up spilling over an A4 page with categories and sub-categories. Reading your post I can see where this went wrong (and why I’ve yet to complete most of the things on my list!).

    It can sometimes be difficult to see the smaller pieces of projects and to isolate them to 3 bite-sized daily tasks, but I believe you’re right that with practice it would get easier and eventually, by sticking at it you can get in the habit of doing these things.

    Thanks again!

    • Peter Shallard on the 13th September

      Hey Anthony! It’s a classic trap eh?

      That said, theres nothing wrong with a list of “things I *could* do” … but you also need a daily (short) list of “things I *will* do”

  2. Jay Meany on the 13th September

    This was a great way to start Monday. We all have our own way of managing to-do’s but the principals are the same and as an entrepreneur important to remember now and again. Thanks

  3. Sarah Hays on the 13th September

    Awesome post, Peter! Totally agree that entrepreneurs struggle with this and appreciate your tips. I’ll be sharing them with my fan base.

  4. Ryan Jenkins on the 13th September

    Stellar post!
    I love the one Post-It idea.

    I find that by putting myself in the proper environments (coffee shops, restaurants, etc) I will be more focused and disciplined to smash my to do list. It is also really important for myself to walk through the necessary steps needed to accomplish my to dos before I engage in them.

    I wanted to surf the web and comment on any good content I came across – check!
    Thx for the insight!

  5. Philip on the 13th September

    Good post and something most entrepreneurs can relate to. I recommend reading the 4 Hour Work Week by Tim Ferris for some more in depth info on how to weed out the unimportant and get things done.

  6. Peter Shallard on the 13th September

    @Jay and @sarah – thanks for the comments. Glad I could pass on a valuable tactic.

    @Ryan I agree that finding the right environment is important. It’s funny how some people LOVE working in cafes and others hate it. I love it, but probably get more done at the office (if im totally honest).

  7. shishir on the 14th September

    Nice article. Just loved it

    Correction required on line : No one is disciplined all the time, but being able to switch it on at the times we need it is the skill the forges business empires

    the forges should be that forges

    • Mike Vardy on the 14th September

      (Ed: Ah, yes. Missed that one…thanks for catching that!)

  8. Illiya Vjestica on the 14th September

    Wicked post, Peter! I’d wish I’d seen this post in the first two months of starting up my business. I’m very accustom to writing huge to-do-lists, that is what was programed into to me in my previous non-self employed life. I’d average out about 20-50 tasks a day and you’re right, far too many to get done in day. It makes it seem like a big mountain to climb.

    I’m going to try out the 3 task a day on a Post-it note, sounds very good. Great tips all in all, looking forward to reading some of you posts in the future.

  9. Jared on the 14th September

    I know it was kind of the irony of the opening paragraph to your post, but discipline IS a form of freedom. Freedom, like the type of freedom a child desires to be free and fanciful and have fun all their lives, is really just imprisoned by their own laziness / selfishness. Grant it, freedom is the ability to decide if I will choose to be lazy, or be productive. But maintaining freedom in the truest sense of the word is to be disciplined enough to maintain that freedom, not just be shackled by something else (laziness).

  10. Work From Home Ideas Guy on the 14th September

    I agree whole-heartedly with Ryan. The single Post-It note idea is a winner. I have using this tactic recently with fantastic productivity gains.

    My gut tells me that the improvement has come from vastly increased focus …

    Thanks for another top-notch post!

  11. Brandon on the 14th September

    Great article – I started using the awesome for setting micro-goals about a month ago and, frankly, it rocks my socks off. It essentially makes these “micro-goals” into a game, which makes accomplishing the little tasks during your day feel fun and satisfying.

    Anyways, great read to get me motivated for my day!

  12. Mike Ward on the 14th September

    Although my business is still a fledgling, I can attest to setting micro-goals as the best way I have found to navigate through a mountain of tasks. Making them achievable goals per the post-it note idea is also important because as you complete them, it establishes a pattern of success, whereas if your goals of the day are too big, you set yourself up for disappointment. Achieving the small victories generates a positive attitude to carry over to the next task.

  13. Christopher on the 14th September

    I love the post it note idea. I’ll be starting that tomorrow. Should help to alleviate some of the overwhelmed feeling I’ve been brewing.

  14. Miss Britt on the 16th September

    Hmmm… I’m trying to think if I’d be able to get everything done each week if I only did 3 tasks a day.

    I’m assuming these are fairly major tasks?

  15. mlambie on the 21st September

    My business partner directed me to this post and Im very glad he did.

    Ironically, reading this post is one of the three micro tasks I will absolutely achieve today 🙂

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