I Was Trying to Skip the Middle

Exactly one year ago, I stepped into a new role and confidently told my VP I was going to close more than $1.2 million in sales.

Mind you, I had never done field selling before.

I was learning a new way of selling, building a pipeline from the ground up, and quickly realizing that I didn’t even know what I didn’t know yet.

But apparently, I knew I was going to crush my quota.

The confidence was there.

The experience? We were going to figure that part out later.

Endings have a funny way of making everything that came before them look like part of some perfectly executed plan.

It wasn’t. Not even close.

You know the beginning, and I’ll eventually tell you the ending.

But first, let me take you to the middle.

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A few months into the role, the excitement of the promotion slowly gave way to the reality of learning something completely new.

In my previous role, people came to me with questions, and most of the time, I knew exactly how to help.

Now, I was the one asking them.

I had gone from feeling like I knew exactly what I was doing to feeling like I was starting all over again.

On paper I wasn’t failing, but I also wasn’t anywhere close to the pace I needed to hit the goals I’d set for myself.

So naturally, I did the math.

And then I did it again.

I would sit at my desk doing the same calculations I had already done approximately 400 times, hoping the numbers had somehow changed since the last time I opened my laptop.

They had not.

The more the math wasn’t mathing, the more I thought about work.

Conversations at dinner somehow found their way back to it. There were nights when I was physically present, but my mind was still replaying my day.

I wasn’t myself.

And because I didn’t know how to fix it, I did what I had always done when something wasn’t working. I worked harder. I stayed logged in later, convincing myself that if I just put in a little more effort, eventually everything would click.

Instead, I started running myself into the ground.

I remember getting on a Webex call one day when a coworker looked at me and said, “Wow, you look like you’ve lost weight.”

I laughed and said, “Apparently that’s one of the perks of this job.”

Everyone laughed, and I laughed too.

But the truth was, it wasn’t really a joke.

Looking back, my body was trying to tell me something long before I was ready to listen.

I’ve always been confident, but I’d also been fortunate enough to have results that matched that confidence. Now, for the first time, they didn’t.

And I started wondering if maybe I had overestimated myself.

Maybe I had mistaken being good at what I used to do for being ready for what came next.

I didn’t say those things out loud very often.

But I thought about them all the time.

I was talking to my mentor almost every day by then. I used to joke that he was going to have to start charging me because this had basically become his side job.

And almost every conversation seemed to end with me saying the same thing.

“I just need a big deal.”

I was convinced that one big deal would change everything. I just needed to find it.

One day, he paused and said, “I’m going to tell you something, and I don’t want you to take offense to it.”

Which, for the record, is almost always followed by something you’re definitely going to take offense to.

Then he said, “You haven’t earned a big deal yet.”

In my head I was like, Excuse me? What do you mean I haven’t earned it? I’m putting in more activity than just about anybody else.

But he wasn’t telling me to work harder. He was telling me to trust the process, which is a really hard thing to hear when you’re impatient.

Especially when you’re me.

I heard what he was saying. I just wasn’t ready to believe him yet.

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Then December happened, and I missed my month. By that point, I’d had enough. I even started looking for a new job because I wasn’t sure I wanted to do this anymore.

Then January rolled around, and I didn’t earn a commission check for the first time in years. In my mind, it confirmed every fear I’d been carrying.

Maybe I really had made the wrong decision.

Then February came.

I wish I could tell you I woke up on February 1 with a brand-new mindset and a perfectly executed plan to turn my year around.

I didn’t.

I was tired of doing the math. Tired of wondering whether I’d made the wrong decision. Tired of trying to force an outcome that wasn’t happening fast enough for me.

At some point, I just didn’t have the energy to obsess over it anymore.

So I did something surprisingly simple.

I just did my job.

I complained less. I put my head down and focused on what I actually knew how to do.

I prospected. I built relationships. I opened doors.

And for once, I stopped looking around every corner for the big deal that was supposed to save me.

And then I went on vacation.

We had booked a family vacation somewhat spur of the moment, and normally, I probably would have told myself I hadn’t earned it yet. I wasn’t where I wanted to be, so how could I possibly take a break now?

But this time, I went anyway.

Maybe I was just too tired to argue with myself anymore. Or maybe it was because February is my birthday month, and I was officially another year wiser.

Let’s go with that.

It was month-end, which normally meant my blood pressure was through the roof as I tried to figure out how I was going to hit my quota. This time, I had no deals coming in and no idea how I was going to get there.

I remember being on vacation with my family and thinking, This is what I work so hard for.

Not to stare at my laptop until the numbers finally told me I was allowed to enjoy my life.

Our vacation had been extended unexpectedly because of a storm back home, but for once, I didn’t care.

On that extra day we weren’t even supposed to have, we were riding the Walt Disney World Railroad, which, by the way, is not exactly the most thrilling ride at Disney, when an email came through.

It was the big deal I had spent months looking for.

By the time we made it around the park and stepped off the train, a few emails had gone back and forth, and I had the signed letter of intent. I called my manager to tell him, and just like that, I had enough to get me to quota that month.

As we walked down Main Street, I looked at my family and said, “Let’s have some fun.”

And we did.

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When I looked back at February, I realized something else. It hadn’t just been the month the big deal finally came. It had also been my biggest activity month of the entire year.

And suddenly, I understood what my mentor had been trying to tell me.

The calls, the meetings, the follow-ups, the relationships. I had been doing the work.

I just hadn’t given it time.

And then March came.

March became my biggest sales month of the year. The work was starting to catch up to the effort.

I still worked hard. That part of me wasn’t going anywhere. But I stopped trying so hard to prove I belonged and started showing up like I belonged.

And the ending?

I ended up having the best year of my career.

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What strikes me now is how impossible that ending felt when I was standing in the middle of it.

No one else expected me to have everything figured out after a few months. No one else expected me to perform like someone who had been in the role for ten years.

I did.

The hardest person to work for wasn’t my boss.

It was me.

I was so busy trying to get to the ending that I completely underestimated the middle.

When I think back on this year, what I remember most isn’t the numbers, the awards, or even having the best year of my career.

It’s the people who answered the phone.

The mentor who cared enough to tell me what I needed to hear instead of what I wanted to hear.

The coworkers who listened to me complain more times than they probably wanted to.

The family who loved me through a version of myself that I honestly didn’t like very much.

Because when you’re waiting for something to finally work, you don’t always need someone to tell you how the story ends.

Sometimes you just need someone to remind you that you’re not at the end yet.