rocket ship

20 Sale Jobs in 20 Years?

It’s sadly the truth. I was so intrigued, I printed out the resume to get a count. Yes, it was true. This guy had 20 jobs in 20 years, they were all sales jobs, and not one of them lasted more than 13 months.

The amazing thing was he was hired time number 10, 11, 12, and even the 19th time. Several people out there had enough hope to give this guy a shot at a new sales job, thinking this time it’d be different.

After I looked at the 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.


Time Grab a Seat on Your Rocket Ship! Here’s Exactly How to Get 20 Jobs in 20 Years


#1 Follow 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 Don’t worry about 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 Always follow your old sales manager around.

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, takes 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 Salesforce.

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

Definitely don’t worry about building internal relationships at your company. You’re a salesperson, so just 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 Very Exciting.

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 Your SDR and Marketing Team for ALL Those Leads You Need.

Your SDR should be able to generate all your leads. Isn’t that what they’re getting paid for? Isn’t that what you were promised? 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, you should only be writing a few select and highly personalized emails. Someone else much less experienced should be doing the cold-calling grunt work for you.