3 Lessons My Soul-Sucking Sales Job Taught Me about Entrepreneurship

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Before moving to Denver in 2010 to take my first (and only) door-to-door sales job, I didn’t know it was possible to wear down the little pegs at the base of high heels… and then start wearing down the posts themselves. I’ll never forget the two-inch black-and-red snakeskin Nine West kitten heels that met their untimely end far too soon.

Despite identifying as an extroverted introvert, I decided to summon the deepest wells of my courage and give cold calling a try. It seemed like a great opportunity: In addition to my low base salary, I was promised an “unlimited income” if I worked hard enough.

But my high expectations didn’t last long. That job was, by far, one of the worst and most stressful I ever had. The company was notorious for having disrespectful and rude salespeople, and the minute business owners heard where I worked, I got a lot of mean, immediate “no”s. Within weeks, I had recurring stomach cramps, constantly concerned about not hitting my sales goals and getting fired. Within 5 months, I drove myself to the local ER only to learn I had stress-induced kidney stones.

Looking back now, I’m both grateful for the experience and amazed at how many positive lessons I took away from the job. Here are 3 lessons I learned working in door-to-door sales that taught me how to be a successful entrepreneur.

1. “Every door, every floor” is a great way to appeal to… no one.

I ruined more than one pair of beloved shoes cold calling for a now-defunct telecom company.

We were taught to internalize this mantra and then expected to walk into every business within our assigned metropolitan radius. Not only was this exhausting, it didn’t amount to much success. In fact, the service I was selling was expensive and often a poor fit for particularly small businesses.

At first, I struggled to let go of the “every door, every floor” mentality in my own business. Thankfully, time, experience, and enrolling in a course by one of my freelancing idols, Ash Ambirge, helped me realize I could pick a type of content to specialize in. 

A separate course from entrepreneur guru Justin Welsh also reminded me I needed to get clear about my ideal client and who I want to serve—something I know well and, at times, willfully ignore. 

Working with my writing coach, Paulette Perhach, has helped me lean into my own voice and run my business unapologetically—niche or no niche.

I no longer subscribe to the idea that I need to appeal to everyone, nor do I need to pigeonhole myself. My content writing and strategy business continues to grow because of it.

2. Selling something you don’t believe in is an exercise in futility.

When I first learned about how to sell dedicated T1 internet and VoIP systems to businesses, my trainer made it sound like THE best option for every business. But hitting all those doors and floors quickly taught me it wasn’t. 

Though I saw some early success running on excitement fumes during my first few weeks on the job, my luck started running out. I started losing faith in the product, and it showed. Every day felt like walking into a trap, and no morning office pep talk could prepare me for a day in the field. At night, I lay on the floor of my apartment living room and wept until I hiccuped. I was so concerned about my plight that I quit eating regularly and lost a whopping 20 pounds.

When I look back, I can see how that lack of belief affected my sales numbers. As an entrepreneur now, I don’t keep trying to push the issue if something doesn’t feel good or I’m not excited about it. I find a graceful way out and go back to services I know I can offer with confidence.

3. My first job is to sell. My second job is to follow up (a lot).

I played a lot of phone tag as a salesperson, punching my Cisco handset number buttons until my fingers went numb. But all that phone time wasn’t just for calling new prospects—it was also for following up with old ones.

I never got anywhere with my sales pitch without a little extra effort and phone coaxing. As a content writer now, I experience something similar when I pitch to podcast hosts, publication editors, and other journalists.

    Few prospects and editors answer me from an initial email. Sometimes, I haven’t even gotten a response from a second. Or a third… And sometimes, a response never comes! But I also know that if I fail to follow up, there’s not a pumpkin pie’s chance in Sharon Weiss’s oven of hearing back. 

    People are busy and need to be reminded that you’re banging your frying pan, trying to sell your offer or get your message heard. As long as you’re professional and kind, no one will think twice about you checking in.

    Every entrepreneur is in the business of sales.

    The year I spent in telecom sales was one of the most stressful of my life. But as it turns out, wearing down those heel pegs did me a lot of good. 

    That soul-sucking job prepared me more for the challenges of being an entrepreneur than any other I’ve had. When I think about it now, I’m grateful.

    Krissi Driver is a freelance writer helping time-strapped business owners strengthen their “know, like, and trust factor” by pitching their ideas for contributor guest articles and podcast interviews and planning and writing blogs and email newsletters so they can effectively reach their ideal audience and sell their products or services. You can find her on LinkedIn.

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