How to overcome procrastination as an entrepreneur - Kathleen Celmins
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How to overcome procrastination as an entrepreneur

The desire to only do the “fun” things when you own your own business can make it hard to overcome procrastination.

As entrepreneurs, we wear so many hats, and we do so willingly. We’re playing the long game. And we’re doing it, more or less, by ourselves.

Which makes the best thing about being an entrepreneur and the worst thing about being an entrepreneur the same thing.

The best thing about being an entrepreneur is decidingwhat to do at any given moment. No boss breathing down your neck is going to tell you “do this now!”

The worst thing about being an entrepreneur is you have to do all the things, even (and especially) the things you don’t like doing.

Example 1: Social media

After discovering we’re doing pretty well when it comes to our content getting noticed by Google, I realized we needed to focus more on social media.

I decided to start by recording myself on video. Our company, after all, got its start by doing video-first content marketing.

I also wanted to work on improving our clickthrough rate from Pinterest.

I bought a Pinterest course, which was helpful but didn’t spur me to actually do anything. (Because Pinterest is a lot of work, and just watching a course on what to do doesn’t automatically make my Pinterest better!)

As for TikTok, I follow a lot of TikTok experts, one of whom said to create a ton of videos on TikTok over a 30-day period to see what resonated.

I didn’t do anything then, either.

It wasn’t until I finally asked for help with both of those things that I finally overcame the inertia from procrastination.

I found out in one of our company meetings that Whitney, who is our writer, also manages Pinterest, and was willing to take ownership of my “get more clicks from Pinterest” goal.

And it’s working!

Jessie, who is our project manager extraordinaire, said if I was able to create videos in TikTok and either publish them or leave them as drafts, she’d take care of the rest.

And that’s working too!

It feels like magic because I don’t have to do much of anything.

But it’s not magic.

It’s Jessie and Whitney… who are pretty magical.

Example 2: Rearranging something to create something new (glorified copying and pasting)

My friend Anne had “create new practice exams” on her to-do list for months.

These practice exams are low-cost trip-wires for her email list. Here’s an example of one.

The hardest part for her was creating the first exam, which she’d done many months ago. But creating the second, third, and however many others she wanted to create was just a matter of copying and pasting and swapping out content, which she’d already had in a different format, ready to be copied and pasted.

It should have been easy, right?

And it was, once she finally forced herself to overcome procrastination that had lasted months.

But it was tedious. Not at all the most fun thing she could have been doing with her time.

“I don’t know why these take me so long,” she said in a Google chat.

Remembering the “Kathleen is the bottleneck” scenario above, I told her my theory:

We do things as employees that aren’t all that fun because someone else is setting the agenda. “Your job is to do this,” says the boss, “and today that means this more detailed piece of work.”

We nod, ask clarifying questions, and do the work. We might grumble, but because someone set our agenda for us, we would simply do it. We’d never put it off.

But when we are left bossless and in charge, we are sometimes a rowboat without an oar.

So we put things off that will help our business grow for two reasons:

  1. We don’t want to do it for whatever reason (too hard, not hard enough)
  2. And crucially, no one is forcing us to do things (especially to overcome procrastionation!)

What are you supposed to do when you’re faced with an “easy” task that stays on your to-do list?

The way I see it, you have a couple of options for tackling the tasks that don’t seem to get checked off your list.

The tasks I’m referring to are the “easy” ones… the ones you feel like you should do… not the ones that everyone hires out. This is not the post that will tell you how to do your own business taxes, for example.

Because I wouldn’t recommend anyone do their own business taxes.

Except, perhaps, accountants.

The first thing to acknowledge is that parts of your projects will be tedious.

“Love what you do and you’ll never work a day in your life!” Am I right?

No, friends. No, I am not.

Let’s keep work in the work zone and acknowledge the inherent tediousness of some of the things we do.

Even on a passion project.

Even if it’s just something you’re doing to see if you can leave your day job.

After you acknowledge that, you can do one of the following two things:

  1. Get assistance
  2. Push through

Let’s explore.

One-time tasks that take longer to explain than to complete 

These should simply get done.

I know it’s not that easy.

But think of the satisfaction of getting that thing off your to-do list, once and for all.

Don’t let those tasks roll over even one more day. Set a timer for 10 minutes and just start working on it. One of two things will happen, you’ll either be done at the end of 10 minutes or you’ll be in the zone and want to finish.

If you need a treat, find one that motivates you. Treats that have motivated me in the past include pedicures, thrift store excursions, some sort of candy… but not until whatever had been on my list too long was finally crossed off it.

If you need some sort of punishment, send someone money, tell them if it’s not off your list by tomorrow that they should send that money, in your name, to some organization you TRULY do not support.

Everything else: GET ASSISTANCE

Friends, we cannot do this in a vacuum!

You don’t have to get yourself a business partner (and why should you? The best business partner on earth is already taken!), but you do not need to be a lone wolf.

In fact, you shouldn’t be.

How to get assistance with those “easy” tasks

If you don’t have a team, or you haven’t had the best of luck finding the right person for your team, I have a couple of pieces of advice.

1. Find the best person you can afford

Work with someone who knows their stuff. Not a beginner. Not someone ten time zones away from you. You can get fancy and find a different level of help later, but at first, hire someone who’s at least at a specialist level.

If you’re worried about what it will cost you, think about the very real cost of continuing not to do the parts of your business that you keep putting off. I guarantee you it’s higher.

2. Set that person up for success

Finding someone who is confident enough to set their rates at a reasonable market rate isn’t enough.

Eventually, you’ll want the person you work with to simply take the entire thing off your plate, but at the beginning of the relationship, you need to over-explain what it is you want.


Set up a checklist if you prefer writing. Take a Loom video if you’d prefer to walk them through exactly how to do the thing.

Or do both. There’s no harm in over-explaining.

The goal here is to tell the very competent person you’ve hired what success looks like for every single thing you want them to do.

Think of yourself as the artist, and the person you hire as the apprentice. You wouldn’t dream of giving them a blank piece of paper and telling them to create whatever they wanted. No. You’d map out precisely what you wanted the end product to look like, then you’d tell that apprentice how to accomplish each part.

As you go through this process, you may find that it’s easier to simply do it yourself.

Resist that temptation. You’re not getting assistance because you aren’t capable of completing your tasks. You’re getting assistance because your brain is better spent on other tasks.

The ones you like.

The ones you wouldn’t outsource, even if you could.

Conclusion: it’s hard to overcome procrastination because nothing about being an entrepreneur is easy

Remember, you didn’t get into this line of work because you wanted employer-sponsored healthcare and 10 days of paid vacation per year.

You did it to change the world.

Or at least your corner of it.

You deserve the clarity and headspace that comes from getting assistance.

It’s one of the best ways to future-proof your business.

Case study:

How we earned $100,000 in a year on a digital product

Get the three things that made the most difference when we marketed a digital course and it earned $100,000 in just 12 months.

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