An Open Letter To My Younger Self

My first day in sales was August 12, 2004, so this past Friday marked my 18th anniversary. That sounds like a long time, except I can’t imagine doing anything else, so in that way it doesn’t feel like any time at all.

I’ve been asked a few times what I would tell a younger version of myself who is just getting into the field. So I decided to write him a letter.

Young Jeff,

Trust yourself. Every time you’ve had any intuition about what’s right or what’s wrong as it relates to selling has later proven to be true. Don’t second guess yourself just because you’re new or unfamiliar with how things should be done.

It’s true. There have been very few times in my career where what I’ve felt is the right thing to do hasn’t worked out, even when everybody else seemed to be going in another direction.

Being new doesn’t mean you don’t know what to do. Sometimes it takes a fresh set of eyes to gain a new perspective.

I still see salespeople repressing their own intuitions every day in favor of looking for advice. "There’s got to be a better way. What do I know?"

You know more than you think. Selling is a people business, and you’re a person. You know how to interact with others, you know your manners, and you’ve picked up on enough social cues to read a room.

Where you go wrong is when you look for too much advice. A talking head on the Internet says you should do one thing. Another talking head suggests something different, only louder. You find so many conflicting ideas that you spin yourself in circles only to end up more frustrated than when you started looking.

It’s exhausting, and you still haven’t gotten any work done.

The dirty secret most sales influencers won’t tell you is that their stuff won’t work for you as well as it does for them. That’s because it’s not yours; it’s theirs. 

You’ll realize that you can never be better than average when you sell like everybody else. It’s literally the definition of mediocrity.

If you want to realize your sales potential, you have to find your own way.

Of course, you don’t need to build it from scratch. The books you read and the podcasts you listen to (from most sources) provide you with some pretty solid frameworks. The key is not to copy them verbatim but to understand why they work and make them your own.

A couple of things happen. First, you don’t feel like you’re running in someone else’s shoes. It’s natural and authentic. It feels right. Second, when you spend time learning why things work, you’re actually mastering your craft. Those skills will be more transferable than you can possibly realize right now.

Now you can unlock your own creativity and do some amazing things. Most people talk about sales careers because the commission checks can be pretty nice. I can confirm that. What most people don’t talk about, because most people never realize it, is the fulfillment that comes with solving problems for other people in a way that only you can and seeing them win as a result. It’s intoxicating.

I know it feels risky, and I know there’s uncertainty, but it’s really the only way. I wasn’t certain about taking my first sales job, but I knew intuitively that there was something I needed to explore. This is the same principle at work.

The road’s going to be bumpy at times and smooth at others. Along the way, do your best to always be learning. Ask for help from the people who have gone before you. Their wisdom is powerful.

But never, ever, forget that you’ll never sell better than when you sell like you.

You have no idea how bright your future is. Keep moving forward.

Love,

You