The other day I had the pleasure of meeting a former start-up CTO for coffee (former due to successful sale, not epic fail). Being at a crossroads in my (so far quite short) career currently and antsy for a change, I really appreciated the insight of an experienced person – as Eleanor Roosevelt said, “Learn from the mistakes of others. You can’t live long enough to make them all yourself.” The following captures the essence of our chat, in part for my own future reference, and in part because I hope that you will find it as eye-opening and inspirational as I did.

1)      “It’s easier, faster, and more likely to teach you the right way of doing things to be “formally” trained than to learn by blundering” – using “formally” loosely here, because what was really meant was along the lines of the Roosevelt quote above: finding and working for (or with) a well-versed pro will do you better than stumbling through stuff on your own.

2)      “There are three things that you cannot teach people: how to be smart, how to work hard, and how to get along with others. Everything else is learnable.” If you possess those characteristics (no need to be modest with yourself), never get discouraged by particulars of a job description. Reach out and “touch” a potential employer to understand whether they’re able to customize a niche for you to fit into.

3)      At the same time, “if you have those three things AND 5 years of experience in various parts of the business”, you’ll be it, not the “green” guy from #2.

4)      Furthermore, “[insert large corporation name here: IBM, Microsoft, etc.] is a great company to come from”, in the sense that there are vast opportunities to move around in a variety of established roles within those large organizations with solid training and mentorship available. At smaller companies, while there’s always opportunity to wear many hats, there is probably less of a chance that stars in any one specialization will be on hand (or that they’ll have any time to babysit you). Read into that quote also that there is no expectation of any individuals with ants in their pants (like myself) staying at the corporation for their whole professional lives, but rather “using it” as a training and learning ground that also pays you.

5)      Switching gears a little, if you are set on working for a smaller, start-up company, “ask them about their track record and why someone can’t take them out in three months”. While that last part should likely be rephrased so as not to come off as an arse, this is a very important point to understand, due to the volatility of start-ups and the whole “8 or 9 out of 10 will fail” edict. While large companies are large enough to endure a prolonged amount of sucking in the market, small companies do not have this luxury, so at least try to ensure that you’re putting your career into capable, experienced hands.

6)      “There are only a couple of reasons that the thing the start-up is doing cannot be reproduced: some proprietary super-genius magic technology that is just too complicated, some form of exclusive access to a juicy customer channel, or that the same team has already come at the problem 10 times before and has made all the mistakes that they could.”

7)      Slightly orthogonally, “if you go to a start-up, you’re almost guaranteed to work more and be paid less. You will get stock, but do your research to know what it’s really worth.”

8)      And, finally, “the economy is still pretty shaky. Those 30-40 employee companies you see now with ‘Mickey Mouse’ business plans may all fail before the year is out. [Insert large corporation again] will not. Spending another half-a-year to a year there in a new, more exciting role will get you more variety of experience and give the economy a chance to heal further. Either way, make sure you understand the risks to the fullest of your ability before making any sudden movements.”