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Dear Quota Team,
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I have been in sales for almost five years, even though it feels like I just started yesterday. In that time, I’ve sold cars, manufacturing equipment, tried staffing, and just started my first software sales role as a business development rep.
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Here is my problem (if you couldn’t figure it out already): I always start off enthusiastic, ready to take on the world and optimistic about my chances to make a lot of money. But eventually, after about nine months (I went back and thought about it, it seems to happen around the ninth month almost every time), I am completely disillusioned with the company and industry I’m in, and start looking for something better.
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I’ve done this at least four times now, and there were another two instances where I quit without having anything lined up and lived off my savings until I found something new. When I think about working in sales, I get motivated, but when it comes to the day to day, I start to lose faith after a few quarters, or find something wrong with the company or people I work with. 
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Is there anything I can do to make sure I stay enthusiastic, or am I destined to be one of those salespeople who hops around their whole career, because if that’s the case, I’m probably better off finding a salary job so that I’m not stressing myself out every time I get fed up. I appreciate any feedback you might have.  
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Noncommittal in New York State  
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Dear Noncommittal,
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We definitely agree that if you can’t learn to stick it out, then you’ll never achieve enough success or make enough money in sales for it to be worth all the trouble. 
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Without knowing much about you, it’s hard to say what the problem might be. If you’re on the younger side, the “big picture” view might only come as you get a bit older and gain more perspective. There’s not much in life that can be achieved overnight, and success in sales takes long, grueling commitment, though it does pay off relatively quickly, especially considering that doctors and lawyers have to go to school for years before they ever see a dime. 
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Here’s our advice: the next time you hit that nine month mark and start thinking about leaving, don’t. Instead, just stay and see what happens. Consider it an experiment. Stay at your company and put in some effort, and see how far you can take it. 
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Here’s the thing about success: small wins give you the confidence to keep going. And eventually, you’ll get a big win, and before you know it, you’ll have an entirely different perspective on the daily grind that so many people can’t seem to stomach. 
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But the only way to get there is to tough it out, put in the effort, and keep track of all your wins. If you can’t make it work at four different companies, it’s probably not about them, it’s about you. The good news is that you can change – you just have to ignore that little voice in your head that tells you it’s time to quit. Good luck!