Be Uncomfortable

In 2021 I landed what would become one of the most important jobs of my career without realizing it at the time.

A software company looking to make waves in the property management world was growing quickly and needed to expand their customer experience department. Having a few years of customer service and sales experience with a background in CRM’s I was, at the time, an ideal candidate for their position.

The environment of a startup is by its nature organized (and sometimes unorganized) chaos. I’ve never worked at a company that wasn’t a start up so there was a lot of common ground from the start.

LeadSimple was growing. Fast. It was growing fast without a sales department. I was looking to make a paycheck, the newly appointed head of sales wanted to create a story for himself and needed to build a sales team.

I’ve never been a big fan of sales. I don’t have the energy for it. Every sales position I held came about the same way. I was hired to do some form of customer success and because the company I worked for was so small, I inevitably ended up participating in a sales role.

Being a people pleaser has its perks. Not knowing when to say no means you’re put into uncomfortable situations. If you combine that with the excitement of doing uncomfortable and learning from it you arrive a pretty sweet cocktail of new experiences that are rarely the same.

So while it wasn’t the first time I was like “sure, I’ll do sales, what’s the worst that can happen” it was the first time I had the privilege to do it at such a scale.

From onboarding new clients to going to trade shows dressed in dark blue suits and attending dinners and mixers and whatnot, I was living a job opportunity I never really expected from my life.

I’m not the party person. I said I don’t have the energy for it. I don’t entertain the idea of talking to hundreds of people every week as something exciting. I thought most people thought that way until I was really pushed into my sales role. Everyone had such high octane energy. this wasn’t some wall street stock broker gang of redbull, beer and drugs but more like nerding out over new conversation tactics and how amazing it is to diagnose and problem solve. There’s some truth to that but in the end it’s trying to sell something whether you want/need it or not.

That being said, the learning opportunities and growth you get from really stressing your comfortability out until it’s paper thin is frightening and extremely rewarding. Long gone are the days where I’ve got to ponder for 30 minutes in my head if it’s worth having a conversation with someone and if I wont make a fool of myself. I will, and the conversation may not go anywhere, but I’m interested in experiencing it all the same. Being trained to ask more thought provoking questions and being forced to have to engage with that skill deficiency led to career changing growth spurts that I still feel to this day.

It’s not all growth though. I wouldn’t want to paint with broad strokes of bight colors and hide all the contrast. I spent 2 and a half years actively pursuing a sales career because I was convinced that this career path would make sense since it was lucrative and I had skills for it which I knew then and know more in hindsight that I don’t have the power for it. I tried pursuing other skills I was particularly good at, software and product, but stopped and took to learning the sales craft seriously when I was sweet talked into taking it seriously. Not anyone’s fault, I was sold. Money, travel, growth opportunities, it was all there, so I tricked MYSELF into thinking I could make something with longevity out of sales.

I could mediocre my way into a reasonable paycheck with the skills I’ve acquired and still get better, but it wouldn’t be something I’d ever enjoy the way my co-workers did.

I will and have fully exploited everything I did learn to further career paths that I enjoy. Consulting, asking good questions, really being interested in the finer details of conversation, having the know-how to command authority in a call and still be friendly and engaging, knowing where to park on a subject and probe further. All of these skills and more have a plethora of uses and it all came as a result of just sticking out like a sore thumb and doing the uncomfortable, doing what doesn’t come naturally to you.