Do What You Dread Most, First

Do What You Dread Most, First

Or, "The Worst Advice I Ever Received"

There are many things I could be doing right now. Some might even say there are many things I should be doing right now. But the truth is, I don’t feel like doing them. Instead, I feel like telling a story.

So—if you will indulge me …

My experience as the founder and CEO of The Starr Conspiracy for the last 20 years or so has been anything but smooth. Today, I enjoy immense success by any measure (quantitative or qualitative) and my work is extremely fulfilling; but it hasn’t always been that way.

Reflecting upon my life with The Starr Conspiracy (so far), I would say that I have played a small but significant role in a spectacular drama—one that (again, so far) has unfolded in three acts.?

In the first act, I am a naive and insecure kid who allows my head to be filled with ideas about how “business is supposed to work.” In the second act, I am a frustrated (angry, even) “entrepreneur” with a goal to change the way business is supposed to work. And in the third act, I am a humbled but optimistic leader with a happy family and successful company.

But for now, let’s focus on the first act. The one where I am a naive kid who allows my head to be filled with silly ideas.?

I started my company accidentally—and with a lot of help from my friends. Long story short, a consulting client gave me money to start an agency (near the turn of the century) wanting nothing more than to be a client of said agency. How about that?!? As many times as I tell that story, I still can’t believe it.?

So I took the money and started an agency. But running an agency was very different from being a consultant. I thought it would be as easy for me as everything I had done before. But it wasn’t. It wasn’t easy at all. And I failed over and over again.

In the early days of my failure, I would take any advice I could get. And even today, I am grateful for that advice (whether I judge it in retrospect to be good or bad). But the worst advice I ever received was from a puffed-up-bully-of-a-man with a lot of grit and determination, but very little compassion or generosity. But hey—when you’re struggling to figure things out, it’s easy to follow the wrong people and to take bad advice. Even from The Bully.

Among many terrible lessons The Bully tried to teach me, the worst was, “do what you dread most, first.” He even had it wood-burned on a plaque in his office (though he didn’t include the grammatically-correct comma). Do what you dread most first. [Feel free to now eviscerate my own grammar.]

Seems like really good advice, right? Especially for procrastinators, right? Want to succeed? Do what you dread most first! [Sic.]

And so I did.?

I worked really hard to create “dread lists” of all the things I dreaded most. I tried to attack those lists first thing in the morning (that time of day when all the self-help gurus say you should try to do dreadful things). And you know what? I got a lot of things that I dreaded done. A lot of dreadful things.

Unfortunately, I crushed my soul in the process. And given that my superpower is audacious creativity! (says me)—the soul crushing part wasn’t great for business.?

It turns out that when you always do the things you dread most, first—you find yourself mostly doing things you dread! And that really sucks. Like become-an-alcoholic-and-pack-on-an-extra-100-lbs sucks. There is no shortage of dreadful things in life (if that’s all you’re looking for).?

A few years ago, I made a big change in my life. I made a conscious decision to do the things that bring me the most joy, first. OMG. What a difference a few years makes.?

When you do the things that bring you the most joy, first … a few special things happen. First, you end up spending most of your time doing things that bring?you joy instead of dread! Second, the things you dread tend to fall away (either because they weren’t important to begin with or you find it easier to dedicate time to some important things you dread [like taxes] because it’s not your everyday death march). Finally, you serve as an inspiration to yourself and others.

I am so grateful that I was able to make this transformation prior to the pandemic. Because (as the founder and CEO of a mid-sized business) if I had spent every day during the pandemic doing what I dread, first … I would have run myself and the company into the ground. So many things to dread. So many.

So here’s my advice to you. [I’m getting to the age where I feel safe offering advice whether you want it or not, whether you use it or not.] Do what brings you the most joy, first. And if you find yourself doing only stuff you dread day after day after day … check out The Starr Conspiracy! We’re hiring. And we do joy first.?

But seriously. Stop sewing the boot to kick your own ass. If you have to screw up your courage every day to get through each day … you’re probably doing it wrong. This is supposed to be fun, right? Life, that is. It’s supposed to be fun.

So turn your personal “dread list” or worry list or task list into a Joy List! Do what brings you the most joy, first. And if you find yourself getting fired or changing careers or whatever because you couldn’t find anything to do that brings you joy?

You’re welcome.