Advice for the Dreamer in You

Every so often, a younger leader, aspiring entrepreneur, or new business owner will reach out to me and ask to pick my brain. Sometimes they want specific advice on a tool or piece of software; sometimes they want input on a client or competitor or growth challenge. 

Most of the time, though, they just want someone to listen. Running a business isn’t always easy – heck, life isn’t always easy – and sometimes, you need someone who will listen to your stresses and worries and complaints until you kind of burn yourself out on them.

I always enjoy these conversations, and there isn’t much I need to say, really. I have learned that when you let people talk, they will usually realize they have their own answers. Goodness knows, so many mentors and friends have done the same for me over my career. I know what it means about my stage of life that I’m on the receiving end of more of these conversations each year; you get to the point where it’s your turn to listen. 

Begin! The Rest Is Easy

My best advice for most entrepreneurs is probably: don’t take any advice. If you’re at the point that you’re determined and bull-headed enough to do your own thing, you’ve done most of the hard work already. 

Amazingly, my boss has had the same name as me for almost three decades. I vividly remember nervously standing in a Chicago bank 30 years ago, waiting in line with a modest check and newly printed articles of incorporation, about to open a checking account for my first business.

My friends thought I was crazy to quit “my real job”; both of my parents, supportive but practical, advised me not to.

I shuffled my feet and glanced around as I waited for the teller. Time seemed to creep by.

Was this my chance to come to my senses?

The woman in front of me was called up next, and as she stepped to the teller window, I saw a sign that had been hidden behind her. It was a small set of neon letters, hanging on the wall, decidedly out of place against the otherwise conservative decor. 

Pink letters glowed at me. They spelled out: “Begin! The rest is easy.” 

The teller called me up, and I never looked back. 

Opportunity and Obligation

I wouldn’t say the rest has always been easy (!), but commitment is one of the hardest parts. You’ve got to make the decision to burn your boats – to close your off-ramps and shut down the “if it doesn’t work out” scenarios that only distract you from what you’ve been called to do. 

And then what? Well, then there’s a long process of learning how to take your dreams and imaginings and turn them into an understandable vision, and how to take that vision and make it real.

This is where I think most of the people I talk with get a bit stuck. 

We are all entitled to our dreams. We’re all entitled to our own voice. Everyone is owed the opportunity to discover what they’d like to express, and then the chance to express themselves, their way.

But you can’t confuse “the opportunity to express yourself your way” with “the obligation for other people to agree, want it, and pay you for it.” Confusing the two is the difference between a career that supports your family (and the families of others) and writing alone, frustrated, in your home office, or resenting others’ success while watching Netflix on the couch.

Once you’ve found your voice, you’ve still got to put the reps in. And these aren’t the reps of dreaming; these are the reps of translation. Your work becomes about mastering an entirely different set of skills from what it took to find and express your unique self: listening to the needs of others, speaking in a language they understand, finding common points of alignment, and learning how to offer what you are in a way others want without compromising your authenticity. 

I’m writing this on the eve of America’s 250th birthday. I know we all look at that event through our own lens, and this year, I’ll look at July 4th through the lens of someone who has worked for himself for nearly 30 years.

To me, it’s a symbol of starting with a dream that life, liberty, and happiness were available to all, and then writing it down in a vision plainly enough that the words could inspire action: “That these United Colonies are, and of Right ought to be Free and Independent States.”

And then there have been two and a half centuries of reps: the arguing, the compromising, the failing, the listening, the course correction, the stress, the mistakes, the long, unglamorous labor of trying to live up to it all, so we can keep trying. 

How lucky are we! 

So begin, dreamer. Begin!