Did it legitimately over the pandemic because I'm a solo consultant/contractor and don't have exclusivity clauses so I manage multiple clients, however, it has come up in interviews when they look at dates because I put them all on my CV.
Key observations to share are:
- the more different the jobs are, the more managable they are, as the complete context switch is as good as a break. It's not task context switching which is costly, it's role switching, which can be uplifting because there is a "you" in between the roles that is separate from each of them. Most highly successful people have intense hobbies for the same reason.
- Lying destroys your mental health. You don't need to lie if you set and relate with clear personal and professional boundaries. It's a kind of moral identity you have to set. Lying is weak, and indicates you've made some upstream errors that you just don't make when you are a pro. I asked a mentor for advice about something once and he said, "I don't get into the kinds of situations where this is even a question." If you are lying, for your own sake, stop.
- Stress really only comes from failing (nobody gets tired of winning, maybe just bored), so having another source of success improves your attitude and that pays off on both gigs massively. Success gives you a refreshing vibe to be around, and most jobs don't provide enough of it, so bringing exogenous success to relationships and work is huge.
- Working as a consultant in large institutions, there are employees and managers who make sabotaging and undermining consultants a kind of sport, so you need the durable skills for handling those people, as if you are doing multiple jobs, your biggest risk comes from people who won't respect your boundaries. That's a general life lesson as well.
- Realistically, nobody questions anything if you are succeeding, so if someone gets "suspicious," it's really that you aren't delivering value for them and it's time to improve or move on anyway.
- Have a plan to invest the increased revenue and don't spend it. You are giving up so much of your life to do the extra work, blowing it on representative and symbolic pleasures is just remedial, and becoming enslaved to the hedonic treadmill is a recipe for burnout. There is no there there. Luxury mainly makes up for impostor syndrome and blowing money satisfies a self destructive urge. If you wouldn't buy it if nobody else could see it, don't buy it.
- Have a plan to outsource or compensate for all the personal balls you are going to drop like new relationships, home and vehicle maintenance, accounting, gym time (get a home gym), nutrition, pet care. If you can do a master's degree while working, you can do a second job, and people with families manage, but if you don't have commitment and buy in from your partner, consider that the additional revenue is just going to become a bigger support obligation when you destroy your marriage making it, so take care.