2. Managing 3 important realities of self-employment

Elena Dexter
8 min readDec 19, 2023

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Self-employed people face some unique challenges. Any amount of effort you put into our business directly benefits you. Therefore, the more you work — the higher your chances of doing well.

On top of that, working from home erases the boundaries between business and life, allowing work to invade more and more of our space.

At the same time, the scope of our personal ‘must do’ doesn’t reduce.

We end up living in a state of conflict, where on the one hand we are driven by the fear that if we don’t work every waking moment, we are going to miss business opportunities. But on the other, we have all of the personal matters piling up undone.

Struggling with this is common and three important things often get overlooked.

1. Conflicting priorities

Due to the limited nature of time (in general), conflicting priorities are a given.

Having to choose what to spend your time and energy on is going to happen and if you don’t accept that as a reality, your chances of finding a solution are pretty slim.

Think about it like this:

Imagine that your available time is a container, where the blue part represents work and green — personal matters.

If we are working more, filling up more of our container’s volume, where does the rest of our personal ‘must do’ go?…

That’s right, nowhere, it doesn’t get done.

So we either need more time to spend on things, which is not always possible or we need to take something out to fit both rectangles into our timebox.

And that is just a basic calculation, which doesn’t take into consideration more nuanced sides of the problem:

  • Not finding the time for certain activities, for example, sleeping, in turn, can reduce our energy levels, making our entire box of productive time smaller.
  • Or how being stressed and overwhelmed is robbing us of the mental energy that can be used for other things

Here is a story to illustrate my point.

Before starting my last business, I was an executive at a small high-tech company and my last few years with them were intense.

It was a rollercoaster of cool opportunities alongside very difficult decisions, for example downsizing the team. All of that had a huge emotional impact on me as I was one of the people in leadership.

By the end, I started developing a lot of health concerns. Debilitating tension headaches, brain fog and fatigue, just to name a few. That, in turn, made it very challenging for me to keep giving the company as much of my productive energy as I used to.

I pushed through it, but when the time came to start working on my new business I realized that my problems didn’t go away with the former job, they became worse.

It was frustrating to admit that I spent too much of my health capital and now had to spend time and energy recovering, wasting precious early startup momentum.

The first step to resolving conflicting priorities is accepting that there are more things we have to and want to be doing in life than we have time for.

And the sooner we make peace with that, the faster we can do something about it.

2. Capacity

The second commonly overlooked root of many planning mistakes is not comparing your workload against your available capacity.

Basically, how large our time box is compared to the combined volume of all the little things we are trying to fit into it.

Planning more than we have time for is a sure formula for not getting some things done. And it could feel overwhelming and disappointing to be drowning in the never-ending flood of ‘to dos’, many of which we have no time to start, never mind finish.

Feeling good about the way you work is a huge part of my coaching philosophy. I believe that each of us has a choice to either plan our days in a way that feels like a million moments of frustration or a million moments of joy, and I think it’s beneficial to adopt a mindset that emphasizes the latter.

You can complete the same amount of stuff in a week, but how you feel about it sets the stage for your continuous progress and productivity.

A long time ago with one of my software development teams, we used a physical whiteboard to visualize our progress. When someone completed a piece of work, they would come to the board and move their task cards between different states.

My desk was facing the board, so I could observe people coming over to record changes. Something that stuck with me for years was noticing how satisfied team members felt moving their tasks into ‘Done’ column. It was a tiny thing, but it had a huge emotional impact on how people felt about their work.

Make sure to take a moment to celebrate the completion of a task, even if it is small and even if the satisfaction only lasts a second.

This is how you can start steering your days toward the ‘million moments of joy’.

I see many people and even full teams or companies regularly plan more than they can physically accomplish in a given period of time.

In this story series, I will share a toolset that will help you make decisions in a way that ensures that all the activities you plan fit into a corresponding timebox.

3. Multiple to-do lists

The last, but not the least harmful productivity trap is having many separate to-do lists.

In startups, I have seen the following situation many times: the team has two bosses and each of them has their own project list. They are able to communicate priorities to the team, but only within their own scope.

The bosses don’t talk to each other to coordinate priorities on a larger, or company-wide scale, so the team ends up with two parallel dimensions of projects that are expected to run at the same time.

Practically, that resulted in constantly switching attention between one or another urgent matter, as one of the bosses remembered about it. The overhead of that alone probably wasted more time than it would have taken to complete both projects.

Without mindful prioritization, this can easily happen to anyone.

Let’s say you have two separate to-do lists: for your work and personal matters; and each list has its priorities.

People mostly commonly approach these lists in one of the following ways:

  1. Move straight down, one list at a time

2. Switch between the two lists, back and forth

The trick is: how do you decide how many items to go down before switching to a different list?

A common answer is ‘Randomly when I remember that something needs to get done’.

In our example, if you go down your work to-do list for 3 steps and then switch to your personal list’s priority # 1, you are automatically making it your global priority # 4.

While its real global priority might actually be # 1.

Now, how about this scenario, which is more lifelike?

In which order will you be working?

Having multiple siloed to-do lists is a huge productivity killer. It distorts the global order of priorities and can potentially leave behind high-value tasks while deceiving us into completing something that wasn’t that important.

Our urge is often to prioritize work, but some of our personal matters can’t be ignored as well.

For example, you can’t forget to pay your electricity bill, otherwise, you will lose power and besides other obvious inconveniences to your life, you also won’t be able to use your computer to work.

Or if you neglect your health and get out of commission for a week, your business will suffer as well.

If you don’t act preventively, you can potentially create more work for yourself, which in turn will consume more of your precious time. Imagine, being late to fix that leaking pipe and now having to deal with taking out walls, mould remediation and sitting on the phone with an insurance company.

This is why the highest-priority items from all aspects of your life need to be considered and compared to each other before you move to your lower-priority tasks.

Also, you need to make sure that you have time for everything you planned for a given period. This way you can move things around with little to no impact.

These decisions are very personal and very subjective. What’s important, though, is that you are making thought-through choices and not flying on auto-pilot.

Summary

To manage conflicting priorities strategically, we need to learn to:

  1. Accept conflicting priorities as a natural part of life
  2. Understand how much we can do in a given period of time
  3. Know how much each task is going to take, so we can decide how many we can plan for
  4. Make sure we feel good about what we accomplish and steer ourselves towards the ‘million moments of joy’ vision
  5. Put our work and personal ‘to-do’ lists together and set priorities on a global scale

Work-Life Harmony series

  1. The self-employment dilemma: is work-life balance possible?
  2. Managing 3 important realities of self-employment
  3. More coming soon…

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Elena Dexter

Elena helps early startups learn how to manage teams in a light, simple and effective way and adopt a ‘just enough process’ mindset and results-only culture.