Hire Yourself as Your Own Assistant

Here’s an idea that’s so crazy, it just might work.

I’ve been using this to get things done for my online business for the last few months.

The Premise

It’s human nature to compartmentalize our life into roles. We turn on and turn off different parts of our experience and personality when we’re at work, with our kids, coaching soccer, volunteering at church, etc.

It’s not dishonest or “fake”—it’s simply that these different roles require or bring out various parts of us. While your sick child might need care, love and compassion, your boss probably doesn’t need those same parts of you.

Most of us also have some experience with delegating to others or having something delegated to us.

The Revelation

A few months ago, I hit a low point in my online business. It’s not that business was bad per se, I was simply tired or bored or what some would call “the resistance” – a natural tendency to give up on creative tasks.

I thought, “if I could have an assistant, I would just have him do ‘X’ and I’d have a clear mind to work on other stuff.” Then the light bulb went off.

I set out to write a list of things I wanted my assistant to do next week—important things, but things that either slipped through the cracks, or weren’t as immediate as “writing content” or things I simply didn’t feel like doing. I imagined hiring someone and handing this list off to them to get busy for the week.

Magically, nearly everything got done that week (by me, of course, since I don’t have the budget to hire) and I made progress I haven’t seen in years.

I then got bolder with another idea—since I was playing the assistant, I began to notice a few things the boss (still me, of course) should be doing. So I put together a reverse list—hey boss, here’s a handful of stuff that would make this business better as well as what I need to do my job.

As you can imagine, most of that got done too, and I got some great ideas on taking things in the business to the next level.

Now I simply alternate weeks or days or blocks of time—sometimes, I’m the CEO and sometimes I’m the assistant. It turns out focusing on one role at a time is exactly what I needed to make both work better.

The Application

There are applications to this beyond self-employment, including personal finance.

Chances are, there’s a handful of things you are doing as a “leader” in many areas of your life: defining the vision, setting goals, dreaming of greener pastures. These are usually fun to do, since everyone loves to imagine a place and time better than the present (more on that, perhaps, another time).

Chances are you are also neglecting the hard work in these areas, the stuff you need to be doing to make sure your goals are met. This is the grind, the work, the tough discipline to get it done.

For personal finance, it might be the exact reverse–tracking expenses or moving money around might be easy peasy, but facing the bigger picture could be the really hard work.

Trying to get both done at the same time is like trying to read and write together, or like brainstorming ideas for new posts and organizing my business receipts simultaneously. It can be done, but it’s neither pretty nor efficient.

Split ‘Em Up

Here’s a suggestion for dealing with your money—separate the leadership from the grind, and make sure you’re doing enough of both.

Here are a few examples of leadership activities:

  • Setting new money goals.
  • Creating short-term and long-term budgets.
  • Evaluating your account structure for optimal efficiency.
  • Rebalancing your investments (or selecting an investment strategy in the first place).
  • Buying or evaluating insurance products.
  • Meeting with family to talk about money.
  • Automating components of your financial life.

And a few of the work tasks you probably do frequently:

  • Entering receipts in your tracking system.
  • Keeping track of progress on various money goals.
  • Tracking monthly budgets and spending.
  • Depositing, withdrawing, and transferring money.
  • Making small decisions and building small habits that impact your bottom line.

Of course, you can always apply this to your business life, too. It works wonders.


Try mapping out what belongs in each category for just one area of your life. Now put yourself in either the leader’s shoes or the assistant’s shoes and write a to-do list for this week or this month for the other “person.”

If you’d like some further reading on the topic of roles, check out Using Life Roles to Organize Your Budget.

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