#002: The Double Edged Sword of Being the Best Salesperson at Your Company

Aug 02, 2023

What happens when you don’t have the desire to do it all again?  



Busting your ass off and becoming one of the best salespeople at your company is a double-edged sword. You receive the perks and accolades that come with being at the top but you’ve also set a high bar for yourself that the company now expects you to maintain. 

So what do you do, when you are no longer motivated to make sales? What happens when you realize that you’re leaving so much of you on the table professionally, in pursuit of more sales?


When you become pigeon-holed by your success

Like most people, sales found me. I don’t believe I was a born salesperson, rather that I was born with some abilities that translated well into sales. 

A few years ago, I started working for a travel company. I had found a sales environment where I could truly thrive selling a product I was passionate about. The incentives, namely money and free trips, heavily motivated me to push month after month for more sales. 

Deep down, I was driven by an internal competitiveness. I liked to beat my own expectations for myself. When I combined this with the massive thrill I got from closing a sale, I was unstoppable. Finishing as the top first year salesperson in the country was simply a byproduct of seeing how far I could push my own limits. 

Once I had proved to myself that I could do it, climbing the mountain again to be the best was the last thing I wanted to do. Why? Because I was sick of selling and I knew that I wasn’t going to learn anything more by doing it.

I still had career-ambition but I couldn’t escape this feeling that there was so much more of me that I was leaving on the table. It was as if I was only tapping into 20% of my skill set. I felt pigeon-holed by my success: that all I could do was be a top salesperson or the leader of a sales team.

So within 6 months of the highest moment of my career, I quit. 


Do you need to get all of your kicks at work?

The argument can be made that you don’t have to satisfy all of your ambitions and utilize all of your skills at work. Work at the end of the day is just one part of life. 

Yet I had these other sides to me like my creativity that were dying to come out more. When I first started at the company, I would leave work feeling satisfied from the sales I’d made. By the end, I found myself leaving work frustrated because all I did was make sales. Sales weren't enough anymore. 

In theory, I could have stayed at that company and dropped back a tier or two in volume of sales to focus on other projects outside work. I could have channeled my creativity into a side business.

Even though it would have required less effort to be an average salesperson, I didn’t really know how to not be striving in my career. It felt like a foreign concept. 

If you’re great at sales, you’ll be great at 100 other jobs

Sales is one of those all-or-nothing careers. When the going’s good, there’s no better career to be in. But when it’s bad, it will gradually (or very quickly) tear apart the rest of your life.

There’s a period in which you can pretend that everything’s ok and push through. But the burnout will inevitably catch up and eventually you just won’t be able to do one more day of it.

Quitting for me felt like the only option. But it might not be your only option. 

If you feel like you’ve lost your sales mojo or that you are wasting your potential, taking a break is a great place to start.

A week off work (or better yet, a month) can work wonders. It will help you determine if you just needed a reset or if you really have lost the passion for sales. 

A break can give you the opportunity to spend time with a person you might have been neglecting (hint: your partner). And it can help you get clear on what it is you want to explore more of in your career. 


Don’t stay in sales just because you’re great at it. 

Dare to explore more. 

You can always go back to selling.

But you can’t guarantee that you’ll have this kind of drive forever.

You owe it to yourself to see where else it can take you. 


Alana Kilmartin



Taking extended and intentionally designed breaks from work is what I specialize in. If you know this is what you want but don’t know where to start, you can book a free discovery call with me using this link


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