computer and man looking at resume

Sales Rep Lands 20 Sales Jobs in 20 Years

The sad truth is, I printed out this applicant’s resume to get an official count. Yes, it was true. This rep had 20 jobs in 20 years, they were all sales jobs, and not a single one lasted more than 13 months.

Amazingly, he was hired even on the 19th job. He must have been a great interviewer. Several employers on multiple occasions, 19 to be exact, had enough hope to give this guy another sales job, thinking it’d be different this time.

After looking at his resume, I decided I wouldn’t ever encourage someone to go to a sales job that didn’t feel right to them, even if I felt they were passing up a high-potential career move.

Don’t Make These 10 Career Killing Mistakes

#1 Show me the base

Focus on the money. Have you seen the cost of housing these days? I’m sure you live in a VERY expensive city. Have you seen the price of strawberries these days? Your base salary is Super important. In fact, it might be the most important thing for picking your next job. NEVER undervalue yourself!

#2 Self-awareness?!

Self-reflection is a waste of time. You already know what you’re good at. You know what matters to you, for crying out loud, you’ve taken all those sales assessments. You’d rather go to the party than sit at home and read!

Man looking at his watch noticing time is passing.

#3 Follow your old sales manager 

People who know you give you the best packages, territories, and roles. You’ll be taken care of and won’t have to worry so much because you have cover.

#4 Don’t bother to investigate the leadership team

I mean, they are all practically the same, right? If they made it to CEO, they must know what they are doing. You aren’t the CEO, so don’t think about it too much.

#5 Every time you close a deal, relax

At the bare minimum, relax and go out for a few drinks, take some time off. I hear tickets to Europe are cheap right now! After all, you’ve worked so hard for all that PTO. It’s time to take a break. Sales is so stressful, seriously!

Woman with glasses on a phone with a mouse with a pink background.

#6 Don’t worry about using that cumbersome CRM

If they want you on the phone and in front of clients, it’s impossible to log everything, isn’t it? Just skip it. You don’t need it. It’s so administrative. Next time around, make sure you find a company where you get more administrative support.

#7 Never be afraid to be yourself and share your opinions with others, especially executives

When your territory, comp plan, or boss change, make sure your executives know how unfair it is. Go ahead and announce your dissatisfaction on social media. I mean, squeaky wheels get fixed, right? Changes wreck your productivity, so you can’t be expected to deal with too much chaos. Maybe take a few days off for your mental health.

Man on couch in scuba gear looking like he needs therapy.

#8 Focus only on selling

Don’t worry about building internal relationships at your company. You’re a salesperson, so bringing in business should be good enough. Just stay focused on that. No need to go out of your way to attend company events. They’re optional!

#9 Your personal life should be fascinating

Keep your personal life chaotic because, after all, you only live once. A chaotic home life keeps things interesting and gives you something to focus on besides the monotony of the daily grind.

Getting your heart broken woman with broken heart.

#10 Rely on SDRs and marketing for leads

Your SDR should be able to generate all your leads. Wasn’t that promised in the interview? Unfortunately, you’re too experienced to make cold calls now! That’s what Predictable Revenue says, and I’m sure your CEO has read it! You’ve come way too far in your career for cold calls. Someone else much less experienced should be doing the cold-calling grunt work for you.