10 Lessons Learned From My First Job in Sales

May 28, 2014


Billy Joel was popular when I was 22 years old, and I was convinced he wrote all his songs for me. I blasted “Moving Out” a million times through my Blaupunkt car speakers, driving 90 mph from SoCal to Northern California. I wanted to prove to the world that “Only the Good Die Young” didn’t apply to me.

I was doing all this because I was in love with my blond, blue-eyed Santa Cruz boyfriend, and nothing else mattered. We spent our days sailing, tanning, and cooking huge vegetarian dinners. I learned about astrology, shamanism, numerology, and mysticism. When I pulled up the “Death” card from the Tarot deck, I decided it was time for a change and traded the “mellow” life to travel 90 miles north to San Francisco.

I was young, naïve, and very brave – I registered for college, found a room in a Victorian flat in the Western Addition, and landed a sales rep job in the fashion industry for a famous denim sportswear manufacturer.

This wasn’t my first job in sales. I’d sold boiler-room style, doing telemarketing for car insurance companies, and worked in department stores. I was intrigued with fashion and business, and at 22 years old I felt like a big shot, working in one of the most exciting sales jobs. It was glamorous, fast-paced, exciting, and very entrepreneurial.

This milestone set the blueprint for my career philosophy and the choices I eventually made:

  • The sales world is my home. I know it and I feel comfortable in it.
  • I need to do what I love, because the excitement is contagious.
  • If I want to be independent and brave, be an entrepreneur.
  • Look for fast-growing industries because I will never be bored.
  • Surround myself with great mentors.

Looking back after all these years, I can see that what I learned at 22 still serves me today:

  1. I learned what it was to be part of a team of salespeople, where your biggest competition is sometimes the person sitting next to you.
  2. I learned how to entertain clients and build relationships that would later pay off in large-sized orders.
  3. I learned how convincing good branding and manufacturing are.
  4. I learned that you actually need very little to sell -- sometimes we only had 2-inch color swatches to sell an entire category of tops.
  5. I learned how to travel and live out of my suitcase.
  6. I learned how important trends dictate so much, and how to sell 6 to 8 months out
  7. I learned how to sell over the phone and gain trust from my buyers, who would just give me dollars each season to buy the line.
  8. I learned how to be extremely resourceful when I needed to get my stuff shipped out to stores.
  9. I learned that good appearance and fashion and looking good are really convincing.
  10. I learned how to carry heavy samples of denim on a rolling rack without it tipping over!

Any Regrets? Not many. I’ve kept to some of the same values today, but here are a few lessons learned about myself:

  1. I have always been extremely career-minded, realizing that other things will be compromised. When I was 22 years old, I was much more interested in making money and traveling all over than I was in academics, so my college years were compromised.
  2. I am very driven and ambitious, and tend to take everything very seriously. I had to learn to sweat the big stuff and not dwell on the small stuff.
  3. It’s great to be motivated to make money, but you also have to save it and learn the power of creating abundance.
  4. An amazing Victorian in a crappy part of town doesn’t mean anything -- location, location, location.
  5. And, oh yeah — love can fizzle quickly. Never move for the guy!