Your most important client: your future self

It’s always good to take some time to reflect on what you want to see from yourself. (Library of Congress photo)

One thing I hear a lot from those who are struggling to work for themselves (or to transition to working for themselves) is a tendency to put non-client-related projects on the back burner.

In the absence of real, actual, scary consequences from a boss or client, we shirk deadlines and procrastinate on the things we aspire to do for our own benefit.

The way around this is to treat yourself — your future self — like your boss or your most important client. In truth, that's what you are.

And as all high-achieving people know, there is no punishment worse than letting down someone who is counting on you, even if that someone is you.

So what does it take to avoid disappointing yourself? Well, you've got to manage your own projects as responsibly as the ones you're doing for your employer or your clients.

This can be really hard to do, because there is always something on the to-do list that yields a reward (or consequence) more immediate than the ones we experience in relationship to our own projects.

To get around this, we need to trick ourselves into experiencing that reward or consequence today, in a concrete way, instead of far off in the future or never.

This is what Jerry Seinfeld is getting at when he says, "Don't break the chain!" He recommends that when you do your creative work, you put an X on that day on the calendar, and then get as many X's in a row as you can.

Do you really want to be the guy who lets down the boss (you) by failing to do the work to get the X? Of course not. So if that regret is something you don't want to feel, you do what you need to do to avoid it. You put the necessary work on your to-do list and protect the time it takes to do that work, just like you would for your other clients (the ones who are not you).

I feel qualified to share my recommendations on this after almost three years of publishing a blog every weekday. I am writing this while journeying along I-95 in New Hampshire (oops, now Massachusetts) on a bus while trying not to be distracted by Brie Larson being a superhero on the TV screen over my head. My biggest client (me) needs it to be published by 9:00 AM EST tomorrow, and I'd rather not stay up late at night or wake up early in the morning to do it. The deadline is non-negotiable, so I've got to do what it takes to make it work. Simple as that.

Is there other work to do? Yeah. I've got to fit that in, too. It takes planning, and sometimes it takes saying no to things. I can't do everything my boss (me) wants me to do. The negotiations between me and me are difficult sometimes.

The thing that keeps me going is that connection with my future self. I know how it's going to feel when the task is complete and I get to click the button. I will do a lot of really hard work to experience that feeling. That's usually enough reward, but there are other perks (free time, relaxation, and downstream benefits from whatever the work itself was meant to accomplish). Thus, there's a self-reinforcing cycle that strengthens the connection between my willingness to do the work now and the goodies that come later.

Like an intense session at the gym, I don't always enjoy the work, but I do enjoy having done it. Maybe my future self isn't giving me a paycheck, but she's the one who I'm doing it for regardless. She's going to be glad, and I'll be glad to win her approval. Both of us are trusting my past self, who chose this project in the first place and put it on the to-do list. We hope she knew what she was doing. So far, so good.

What is the work that your future self would appreciate you for? What would you be glad to have done? How can you set up your life so that you take it seriously, just the way you set up the work someone else is paying you for? As always, I'd enjoy hearing what comes up for you.