There are obvious moments in life when you know you need to change jobs. Then there are other moments that you don't realize it you should and it could have a bad long term affect future opportunities. For me there are two big ones of those:
#1: When you know too much.
This is the opposite of what people really do. When you do your job well, you know everything, everybody around you regards you as the "master" on that job, why would you change jobs? Unless you are making mid-high six-figures salary the reason is simple: everything changes. The world changes, the customer changes, the product changes and you are hanging your hopes on the basis that things will stay the same.
Changing jobs will give you the opportunity to learn something new (I know, it is a lot of work, even less motivating if you are building a family) and adapt to a different situation. In my view people should change jobs every 2 to 4 years. That is enough time to learn the new job well and not long enough to make you too comfortable and unprepared for changes.
My definition of changing jobs is quite broad. What I mean is that you don't have to change companies. Changing functions, departments, product groups is good. Changing company is better.
I have two easy red alerts when I'm reviewing resumes.
First is people that have 10 years they graduated and already worked on 7 companies. I toss this resume immediately. Don't try to tell me you were unlucky with the companies you choose to work for, because that tells me you are not good at judging opportunities.
The second red alert is when people have 10 years of experience working on the same company, on the same division, just escalating the corporate latter (from individual contributor, to technical lead, to team lead, to team manager, etc.). That tells me you are not a risk taker, not an opportunist. Not fit for a Startup (or a dynamic group).
#2: When management changes.
This is risky advice, but whenever managament either leaves the company or group (to "spend more time with family"), or they are forced out (to "spend more time with family"), or a more qualified person is hired to manage the company/group... It's time for you to leave.
The key here is that a new person/team is in command, and this person/team doesn't know you. They didn't interview you, they didn't made you an employment offer, they didn't groom/mentor you they way they think it is best. They "inherited" you.
If it was easy they would bring somebody they trust and they think is a good fit to replace you. And it has nothing to do with you, personally. It is just you are not familiar to them.
You have three hills to overcome to be valued on the "new team".
First, you have to be very competent on what you do (being ok won't cut it). Second, they have to get to know your work and you (and can't be by your own mouth). Third and finally, they must believe that the new direction of the group/company has a place for you.
Now, imagine that you leave to work on another company/group -- as the management team also leaves. You were interviewed by a group of people that said they want you on the team. Your new manager approved that and he has been looking for somebody for a couple of months already, so he is kind of in a hurry for you to succeed. Not only that, but he (and everybody else that helped you get there) will look really bad if you don't do well because they were the ones that said you would be great.
Here is the difference between the two scenarios: New management with you trying to prove yourself like hell versus you on a new company with a group of people very interested that you succeed.
Rick Segal writes The Post Money Value blog. One of my favorites because of his honesty about the VC business (most other VCs bloggers suck). I met him personally once. He was a straight shooter.
"...An EBF happens when a founder wakes up one day and 'flips' into employee mode. To me, nothing is scarier then a founder saying 'It's just a job.' ..."
This is a great post, worth reading if you're an entrepreneur or investor.
I agree with everything he said. Founders are founders. It is a risk-reward thing. Don't want the risk? Go work for Google or Microsoft.
On the other hand of the coin, I see that investors try to swing every single term to their site (that is their job after all).
Liquidation preferences, negotiate equity stakes that includes the option pool (which is a fantasy), anti-dilution provisions, preferred stock, expenses paid by the company, and the list goes on and on. Rick even wrote a couple of posts about absurd deal terms proposed by investors.
I wouldn't expect nothing less from an Entrepreneur than his/her blood. But most of the time investors don't treat Entrepreneurs the way they should, and that is the cause of angst and some entrepreneurs thinking like an "employee".
Yesterday I was talking with my wife about that I don't feel like I didn't get anything done with my life so far. I did a lot.
I graduated from college, I worked at small and large companies, I lost my father, I opened a startup when I left college, I opened a startup 10 years after I left college, I went to many concerts, shows, events, seminars, conferences. I travelled to many places, many times. I've got married. I had a wedding party. I went to many parties. I bought a condo. I sold a condo. I bought a house. I had a horrible junk car. I had my dream car. I planted a tree. I wrote a movie script. But above all, I had a kid this year.
That is some pretty good life by my standards. I feel I've done a lot, and there is so much more to learn, visit, know, experiment, try, do.
Overall, since I was a little kid I always felt lucky. Very lucky. I didn't know why, but I always got what I wanted. Later in life I realized that I didn't get always what I wanted, but those moments didn't matter and that is why I forgot about them.
But the thing that define my success in life so far, is not the money (which I don't have), or the house, the car, my career, my business. It is the amount of people around me that genuinely enjoy being with me. I have about 50 best friends and another 100 close friends, and a wife and son! How can anybody ask for more?