My edit and update to this post:
I'm on the detractor side of over employment for sales people, but hardly anyone is playing devil's advocate in the comments. It's became quite an echo chamber here. Because of that I am going to do a SWOT analysis so we can really dig into the feasibility of this for sales.
- More income with two base salaries, stock options, company perks, and commission isn't what it used to be in this tech recession.
- This seems contradictory, but less stress because if one of your boss' is on your ass, at least you know you have diversified your ability to hold a full time job if you aren't able to come together with that boss.
- Hard and loyal workers get punished with more work. "Maybe if I work hard, go above and beyond and never take any time off, my company will appreciate it and reward me." Bullshit. You are a line on a spreadsheet. I've built annual sales plans with investors involved and have seen this first hand.
- You find out that you were hood winked in the recruiting process and got yourself into an awful organization? You gotta keep that tenure so stick it out for two years, or quit and just work at your other job, and remove this job from your resume.
- How often are offers being rescinded, just after you gave your two weeks notice to your employer? This is disastrous, and by taking the offer while not giving in your 2 weeks notice, gives you the ability to trial out the new gig to see which of the two jobs you wish to keep.
- Extreme risk of burnout if you treat over employment as being two 40 full time jobs. Impossible, or at the very least detrimental to your mental health and relationships.
- Extreme paranoia. Two monitors? Meetings potentially happening simultaneously? Needing to have camera off, muting on one meeting and then meeting on the other? Conflicting travel to be in the field? This thought gives me ulcers.
- Potentially finding less fulfillment in driving impact for a mission you might believe in. With two jobs (or 3 or 4 jobs if you are a coked out lunatic) you would begin to view your jobs as "clients."
- Freedom and flexibility - similar benefits to being in a FIRE position.
- Asshole of a boss? Or incoming layoff? Who cares, you have another job and won't be jump hunting for 3-6 months in this economy.
- The key to all of this is having an exit, or end goal. Is over employment sustainable long term? No idea, I haven't done it, but I highly doubt that it is sustainable long term. The goal should be to do it until you are out of debt, until you reach your net worth goal in investments, until you take $30k for cocaine and strippers in Vegas, buy a rental for passive income, etc.
- Much faster track to accumulating wealth to then invest in the stock market to expedite your retirement.
- More money more opportunities. Be able to go all in on the business you wanted to start, become an angel investor, etc.
- If looking at a start up for a potential exit, you are doubling your odds (even though we all know those odds are still very, very low).
- This one is very scary. Sales requires LinkedIn. The rule for non-sales people who do unemployment is to hibernate their LinkedIn. This looks sketchy when LinkedIn is such a pivotal part of sales.
- If you are discovered executing over employment, it could torch your brand. To mitigate this risk you ONLY could ever do it with remote roles, and try and do it with smaller companies that are well out of your home state.
- It's just too much and you end up getting fired by both jobs, or you become a cuck investing for your wives boyfriend.