Would I do this for 10 years?
danshipper.com
danshipper.com
I asked myself (now 27) this question when I was only one or two years older than 20, and realized I needed to make a change from what I was doing. My mind has certainly changed several times since then, and I expect it to change several more, but the initial "no" answer was crucial to getting me out of what was essentially a career in tech support.
> Am I learning? Importantly, am I learning what I want to learn?
This was the key takeaway from the post for me. It's something I ask myself regularly as well.
If you are a curious enough person, there are so many thing you would be happy learning though. I've found it much harder to assess: "Is this the thing I want to be learning more than any other things right now?
In other words, if you see yourself working on something for 10 years then it is probably the right thing for you to be doing at the moment. If you are still in the 10 year camp it means you probably are good with a 2-4 year commitment. That is important and helpful for a startup. Making that a metric doesn't mean you will actually be there doing the same thing in 10 years. If you do it with commitment you likely will not be in the same location, role or both within 5 years.
I have 2 successful companies (one consulting/services and another subscription business) and neither one is attractive to me for 10 years. I'm in about year 5 for both. I went into both knowing that they wouldn't excite me for 10 years.
They both excited me to build though. Entrepreneurs often like the challenge and the process of the build. So having a shorter time frame or commitment is not necessarily a bad thing. Some people are good at, and enjoy, incubating.
"Can you stick with anything for 10 years?" or "What else have you done that demonstrates long term perseverance against adversity?".
The real question is whether the person has the ability to persevere in adversity.
No matter what you are starting, your activities will be quite different far sooner than 10 years.
Passion for a particular mission is helpful, but you must be able to handle the drudgery and adversity -- even the most exciting and pleasant pursuits include many tasks that quickly turn to drudgery, and things will go against you often.
It is not passion that gets you through the drudgery and adversity, it is the perseverance. Many passionate people quit when things get tough, while many people with perseverance have made a success of projects with merely "worthwhile" goals.
[edit: clarity/punctuation]
... but, just curious, is your procrastination the same in year 10 as in year 1?
The conclusion is — motivation is complex. It's hard to understand what makes people stick and no set of objective questions can possibly answer if people will be resilient if things fall apart (which usually do in a startup). Gabriel Weinberg worked for more than five years on DuckDuckGo before getting the first taste of real traction[1]. Some may have worked on a similar scale without even getting any significant success.
Although, humans are fickle by design, it seems some motivation is sticky. That's probably the difference between doing Supply Chain Management and building a Google competitor. The former seems to be an impulsive idea triggered by recently gained facts but the latter seems to be working on something you actually believe in.
[1]: https://www.linkedin.com/pulse/motivation-being-cusp-somethi...
I think one of the main thing this advice misses is that if you're doing a "lean startup" then you could very well end up doing something different than what you started. It's hard to know what exactly the continuation will be in what you do.
It's unlikely that this interpretation corresponds to what Jiro meant, since it essentially tells you to practice being an opportunist every day, rather than to practice a more narrowly defined occupation in greater depth. But it's one way to accept both pieces of advice without disagreeing with either :P
I'd work on my current engagement for as long as they'll have me because it's an intersection of the life interests I keep coming back to. I love going to work every day. But wow, am I ever glad I played those other "2 years, tops" roles.
The secret is to rationally analyse your own values, identify why you value what you value, and try to define what unites the different tasks that you have found meaningful in the past.
This post contains some hints of the framework I used: http://aristotleadventure.blogspot.co.uk/2008/05/what-is-cen...
Once your time spent at a single company with high stress, multiple people, and fast growth is measured in years and not months, VCs stop asking you this question.
"Do you want to be bailing out a sinking boat with them for the next 10 years?"
Now that I am nearly a 50-something myself, I still think its the most important question to ask!
How does what you are working on now build on what you were working on before?
Steer toward hard and long-term problems, but keep the momentum you have already built.
The question of working on something for 10 years is less relevant in entrepreneurship, because your role and the nature of what you're working on should be highly dynamic and therefore unpredictable.
One should question the mindset instead. Here's what I now tell anyone getting into entrepreneurship to consider: when what you're working on flatlines in 1 to 2 years, do you have the resources and the courage to keep going? I've seen untold numbers of very capable people try their hand at it and then give up after a year or two. That's a waste. And more to the point, it's also a good way to squander much of the value of what you may have learned in the process.
The question is about the future, but the answer is about the present.
A better question, therefore should reflect this reality. Something like: "Do you feel like your current interest and enthusiasm for this would keep you going for years here?" (or better worded...).