I landed on timeshare. Why timeshare? Simple. Because in timeshare, people come to a resort to get discount tickets thinking that they're just there to go on a golf cart ride. And by the end of the 90 minutes, they're signing up for a $20,000 purchase. (Timeshare reps had been selling high ticket before high ticket was even a thing.)
So I thought… well, what better place can I learn how to become a master closer than the wild world of timeshare?
In the beginning of days of selling timeshare, it was fun. But it very shortly turned into one of the most stressful experiences of my entire life.
I would meet nice families, we would get along great. And then as soon as it came time to get to the sale, they started accusing me of being pushy, being aggressive, just caring about the commission. In their eyes, I was transforming from Dr. Jekyll into Mr. Hyde.
It felt really frustrating to me, because in all honesty, I had good intentions.
Despite their accusations, I knew deep down I care about people. I want to see people succeed and want to see people living their best life.
And I hated making these families feel like I suddenly switched from friend to enemy at the end when they weren’t gonna buy. It deeply affected my psyche.
I wanted us to feel like we're on the same team, but I just couldn't figure out how
It constantly led me to a situation where I would walk out of the resort. And I would literally need to go drink, smoke, or binge eat my emotions away.
Anything to escape those negative emotions because I was drowning in this bad-feeling cocktail. It became overwhelming. Resentment, frustration, shame, guilt, sadness, fear, and disgust–all mixed together in a blender with whipped cream and a cherry on top.
It struck me looking at the salespeople who were leading the pack in terms of sales and commissions. Most of them had traits that I just couldn't identify with. It felt like the Ghost of Christmas Future was showing me the ugly version of myself I would become if something didn’t change.
They were arrogant, pessimistic, and conniving.
Many were even full-blown sociopaths and con artists. And I truly understood why so many people think salespeople are thieves.
Playing in timeshare was a Win-Lose game.
And really, for me, it was a Lose-Lose game.
Because either I made a sale but I didn't do the right thing by the person.
Or I didn't make a sale. I wasted a day of my life. I went home empty handed - feeling like a loser and a cuckold.
It always basically came down to two choices.