Leaving Work Behind

How to Be Your Own Boss (5 Invaluable Tips)

Written by Ransom Patterson on October 4, 2016. 6 Comments

An empty boardroom.One of the best things about self-employment is the flexibility it gives you. There’s no boss or company telling you when, where, or even how to work. This freedom lets you do cool things like go on a 30-day solo bike tour or move abroad to learn a new language.

However, it’s not all fun and games. Working without a boss means more flexibility, but it also means more responsibility. As a one-person operation, it’s up to you to plan, assign, and create high-quality work. With all of this additional management responsibility, it’s easy to let your creative output suffer – especially if you’ve never had to manage your own work before.

Don’t worry, though. In this post, we’re going to show you how to strike the right balance. We’ll give you five invaluable tips for being your own boss, while still producing outstanding work.

Let’s get started!

Tip #1: Set Clear Boundaries Between ‘Making’ and ‘Managing’

There are two types of schedule, which I’ll call the manager’s schedule and the maker’s schedule…Each type of schedule works fine by itself. Problems arise when they meet.

– Paul Graham, ‘Maker’s Schedule, Manager’s Schedule’

The key to being your own boss is first understanding what a boss even does. There are as many ways to define this as there are companies, but I like to think of it principally as the difference between ‘making’ and ‘managing’.

Here’s what I mean:

  1. Making. What most self-employed people think of when they hear “work.” It could be writing, designing, programming, or anything else. This is usually what clients or customers pay you to do.
  2. Managing. This is the behind the scenes work that lets your business function. It includes things such as creating your to-do list, scheduling meetings with clients, and sending invoices. Unless you work as a virtual assistant or remote manager, this probably isn’t what clients pay you to do.

When you run your own business, you have to do both to succeed. However, you should definitely set clear boundaries between the two activities. If you don’t, the quality of what you make could suffer.

If you’re struggling to ascertain whether a task counts as either making or managing, ask yourself this question: Do clients or customers pay you to create it?

If the answer is “Yes”, it’s a making task. Anything else probably falls into managing territory – unless, as the definition above mentions, you get paid to manage people.

Tip #2: Complete Management Tasks in Batches

Once you’ve figured out what counts as managing and making, you need to make sure the two activities don’t interfere with each other.

I’ve found the best way to do this is to complete all of your managing tasks in chunks. In particular, schedule them for a time when your energy levels tend to be lower. You can do this both on a daily and a weekly level.

At the daily level, this means saving the afternoons for things such as meetings and responding to emails from clients. I reserve the mornings (my highest energy time) for creative work such as writing and editing.

On a weekly level, I save Sunday afternoons for tasks such as sending invoices and creating my schedule for the week. That way, these tasks don’t get in the way of my weekday creative work.

You can schedule your management tasks whenever it works for you – the key is to do them in batches separately from your making tasks.

Tip #3: Schedule a Regular Meeting With Yourself

I already mentioned that I take time each Sunday afternoon to complete certain management tasks. In addition, I also use this time to hold a weekly meeting with myself. It’s similar to the weekly progress review meeting you’d have with your boss in a regular nine-to-five job.

During these meetings, I ask myself the following questions:

  1. What are the three things I accomplished this week that made the most difference to my business?
  2. What three things could I have done better with this week?
  3. What’s the one thing I want to have accomplished this time next week?

Once I’ve answered these questions, planning my week is easy.

To make these meetings a success, take them seriously! Put them on your calendar and give them the same importance you would a meeting with a real boss.

Tip #4: Outsource Management Tasks as Necessary

While batching management tasks can free up a lot of time for your making work, there are some tasks that may be worth outsourcing entirely.

Of course, your budget and comfort level will determine what exactly you outsource, but in general I would suggest outsourcing anything that meets the following two criteria:

  1. Clients don’t directly pay you to do it.
  2. It isn’t crucial for you to be directly involved in it.

For me, this makes outsourcing something like filing my taxes a no-brainer. While I could theoretically do it myself, I’d much rather take that time to write articles for a client or improve my blogging skills.

On the other hand, the above criteria shows me that I shouldn’t outsource something like creating my weekly schedule. Clients don’t pay me for it, but creating it myself is crucial for doing my best work.

As far as what it means to outsource work, it could include using an app that automates time-consuming management work, hiring a part-time virtual assistant, or any number of tasks and activities.

Wherever your outsourcing needs fall on the spectrum, I recommend the following resources:

Properly using the above services can clear room on your plate for the work clients pay you to do (and that you actually enjoy!).

Tip #5: Evaluate Your Self-Management

Finally, we have self-management. Even though we may leave conventional work behind to escape a demanding boss, we can often end up being the most exacting. To keep you from being an awful self-boss, it’s important to periodically evaluate yourself. I do this every quarter, along with a larger business review.

The process is simple, and consists of one question. Imagine for a moment that you’re someone else, look at yourself as a manager, and ask, “Would I want to work for this person?”

If the answer is “No,” you’re being too demanding of yourself and need to set more manageable goals in your weekly meetings.


When working for yourself, it could be difficult to strike the right balance between doing and managing your work. Struggle with this, and you could soon be hankering for the comfort of your old nine-to-five.

However, as long as you keep the following points in mind, you’ll be on your way to being the best boss you’ve ever had:

  1. Set clear boundaries between making and managing.
  2. Complete management tasks in batches.
  3. Schedule a regular meeting with yourself.
  4. Outsource management tasks as necessary.
  5. Evaluate your self-management periodically.

What tips do you have for being your own boss? Share them in the comments section below!

Image credit: pashminu.

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6 Responses to “How to Be Your Own Boss (5 Invaluable Tips)”

  1. Jane Osuagwu
    October 7, 2016 at 8:26 am

    Great tips.One of the benefits of been your own Boss is the freedom it gives you to attend to other things, but you will have to be disciplined to set boundaries between your business and life.The success and failure of your business lies in your hands.

    • Tom Ewer
      October 7, 2016 at 8:49 am

      Jane, for some that’s a scary thought – for others, liberating. The important thing to know is that either feeling is completely normal!

      Thanks for your comment. 🙂

  2. Brian
    October 16, 2016 at 7:04 am

    thanks for the tips. I am on my way to be the big Boss!. Hhehehe 😀

  3. Oge Ndukwe
    December 4, 2016 at 12:25 pm

    Thanks for this awesome and productive tips.

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