This question comes up in various ways, multiple times per month, and it came up in a chat I was having with Seattle angel investor Ken Glass today as he mentioned giving similar career advice to some students recently.
Either it’s someone asking me whether they should go work for a startup, or for a big company. Or it’s someone who asks me my advice about which job opportunity to take (or pursue), when they have several options.
My answer is almost always some variation of, “go for the option where you’re working with the best boss, and the best team, and for a company/product that you’re excited about.” Don’t optimize for salary, or even title; and potentially pick your 2nd or 3rd choice company, if it means working for a star, and with a great team. If you do pick well, you’ll follow that person’s rise through the organization, and you’ll have more opportunities than you know what to deal with. That same great manager will make sure you get exposure and recognition for your efforts. And they’ll tell you when you screw up, and help you avoid repeating mistakes. They won’t sugarcoat this important developmental feedback, and you’ll love them for it.
It’s hard to exaggerate how much leverage this simple choice can make, as it can fundamentally alter your career trajectory in good or terrible ways. I’ve seen people make the wrong decisions, and you can literally see the ripple effects through their resumes for years and decades. And at the same time, I regularly see it in positive ways with young stars — making these smart choices early on will benefit you for a lifetime.
Good stuff
The “sensei principle” goes beyond tech…
Had Kareem Abdul-Jabbar not gone to UCLA to play for John Wooden or had Plato chosen not to study under Socrates, neither would’ve been among the greatest of all-time at their respective crafts.
Personally, I’m far from a 6-time NBA MVP or a legendary philosopher (anyone who’s either played basketball or spent more than 3-min w/me can attest to either limitation 🙂 ), but … I did get to work for the 2 most talented people I’ve ever worked with in the early stages of my career: Dave being the 1st, Rand Fishkin being the other.
And … there’s not a single day where I’m not in some way thankful for the minimum wage-ish salary I had at TeachStreet or the osmosis that ultimately changed the course of my life in ways I never could've imagined.
My $.02:
1. Look at your earning potential over a 5-10 year horizon, not a single year.
2. Always work for people whom you respect enough to want their respect.
That's very nice of you to say, Sam. I've rarely seen anyone work harder, or with more entrepreneurial passion than you. What are you up to now? Still doing the marketing training videos? Have you checked out SkillJar? I'd love to see you using their platform, both because I think you'd love it, and also because you'd probably have great feedback for them — I invested in them last year, and they're based down in Pioneer Square (I was just at their office warming yesterday — reminded me a lot of the original TeachStreet HQ, but much nicer!)
Dave – No more consulting or marketing training on my end. A side project of a side project took off & became my full-time gig about 18 months ago. Would love to catch up next time you're up in Seattle!!!
In the meantime, I'll tell you something you used to say to me weekly: "This post didn't suck … you should blog more, mofo!!!" 🙂