How to Flip Any Feared To-Do List into One You Love

A simple three-step framework to get you from loathing to joy

Sophia Sunwoo
Mar 19 · 6 min read
Melanie Wasser

There are a set of tasks all of us absolutely loathe doing for our business.

Social media marketing, financials, and sales calls are usually the top ones, but you can insert any feared to-do list item in your head into this exercise and it’ll work for this framework I’m about to show you.

I am at a point in my business right now where I don’t do any work I dislike. It’s not because I got them off my plate. It’s because I’ve used a framework to help me shift the perspective I hold around those tasks.

I discovered this framework when I had a series of clients come to me with the challenge of replacing Instagram, a major marketing channel for their business, with something else. Despite the platform functioning as a strong lead generation channel for them, they just hated everything about it from the constant content they had to create, the interactions they had on the platform, and its superficial environment.

I spent a lot of time ruminating on this problem, and it led me to create a framework to help business owners understand the root of their distaste for a task, rebuild their relationship with that task from an empowered place, and then execute on the chosen shift.

This shift helps entrepreneurs find joy in their most disliked tasks, which ultimately helps them execute better on said tasks, and become stronger entrepreneurs that can resolve their problem areas.

Here’s my three-step process to creating a more joyful relationship with your most feared to-do list items, so that you not only enjoy these tasks when you’re doing them, but so you end up performing better as a business.

What do you hate about it? And how does it make you feel?

In order to rebuild the relationship at hand, you need to deeply understand what you don’t like about the tasks that ail you.

Here are some guiding questions to help you reflect:

  1. Do you dislike this task because it raises insecurities or fears you have? If not, move to question #3.
  2. If so, what is at the source of this insecurity or fear? What don’t you like about the experience of completing the task?
  3. Do you dislike this task because it’s boring, annoying, or uninspiring to do?
  4. If so, why does this task provoke these emotions? What don’t you like about the experience of completing this task?

To contextualize this for you, here’s how these questions play out for some common scenarios —

Let’s say for example, that you really dislike making sales calls. You don’t like the constant rejection and the vulnerability of constantly putting yourself out there. It makes you wildly uncomfortable to ask people to support your business, and you feel awkward when you have to ask complete strangers to buy from you.

Or, you may find it really irritating to create social media content. You find it to be an incredible slog to constantly create new content and it takes so much of your time to make. From creating the visuals, thinking of captions, and going through the motion of customizing appropriate content for different platforms, it feels like a soulless task that you do just because everyone else says it’s important.

Break the rules and create your own

Now that you’ve done some work on why you dislike this task, I want you to challenge how you’re completing this task.

Who taught you how to complete the task in the way that you’re approaching it right now? Was it an approach that you created for yourself? Or is it an approach someone else told you was the best way to go about it?

I’m willing to bet that 99.9% of you reading this are using an approach borrowed from someone or something else. And that’s probably why you dislike doing this task the way you’re doing it. You’re following someone else’s rules. You also may be using an approach that’s incompatible with your personality, strengths, and/or skillsets.

The first thing we need to do here is to completely deconstruct the approach you’ve been using and rebuild one that feels right for you. This way, you create your own rules while customizing them to your skills and preferences.

Kick this off by thinking through a time or moment when you actually enjoyed doing your task from your dislike list. Did you like it because you were on a sales call selling to a friend? Did you like how natural and unstuffy a particular sales meeting felt? Did you really enjoy creating social media content for a creative project because you were able to let loose on images and captions in a style and voice that you enjoy?

Whether this instance is a real or imagined scenario, process what your desired way of completing your dislike-list item is like if you broke all the rules, neglected “best practices” and only prioritized joy while you were completing that task.

Some scenarios to contextualize this in action — if you were to create your own rules around your sales calls so that you enjoyed it more, you may decide to ditch “cold” meetings and calls altogether because they feel inauthentic to you.

You may instead, decide to have get-to-know-you meetings with potential clients and only pitch to those that you feel are ready to move forward. You already love meeting new people and getting to know them, so this feels more aligned with your personality than doing cold call drive-bys.

If you were to create your own rules around your social media content so that it felt more fun for you to create — you may decide that you no longer want to create education-driven posts because they bore you to death to make.

You may decide instead, to replace this content with quirky education posts where you can share interesting opinions and perspectives you have while pairing it with some funny meme you’ve created. You absolutely love memes and creating them for friends in your free time, and creating them for your business sounds incredibly fun.

Create the shift

After you’ve dreamed up this scenario and explored what joy feels like to you when you make up your own rules for tasks you dislike, create a new process or approach to actualize that shift.

Trying out a new approach with rules you’ve made up is going to be an experiment at first. Things are going to look and roll out differently. Expect this.

For example, shifting the way you approach sales prospects is going to change the timeline of how quickly you convert leads to sales, but you may find through this experiment, that the approach you’ve chosen actually helps you close the same if not more sales than you were before because you now have the stamina to talk to more people in a state of joy.

Or, when you’re testing out your new social media content style, you may find that you need to tweak a thing or two to make your content more resonant and poignant for your audience. This process may take you a few more months than you anticipated.

I recommend respecting the process, being patient with yourself while you’re experimenting with this, and being diligent about the revision stage while you get this task to a state of enjoyment. Even if it takes a few rounds at first, you will eventually get there, I promise.

While you’re on this long marathon of building a business, finding small ways to find joy in the tasks you must complete are essential for your sanity, and to also keep you in the game for the long haul.

For more content like this that turns your startup chase into a victory lap, get my Friday morning emails, (lovingly called The Crux) in your inbox.

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Sophia Sunwoo

Written by

I create moneymaking brands with womxn entrepreneurs who refuse to settle for mediocre. www.ascent-strategy.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +794K followers.

Sophia Sunwoo

Written by

I create moneymaking brands with womxn entrepreneurs who refuse to settle for mediocre. www.ascent-strategy.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +794K followers.

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