Create Milestones for Your New Job

People are afraid of taking new jobs. There is a risk of failure of the company you’re joining and potentially of yourself in the role you are accepting. But we all need to accept new jobs at some point. What you should think about is how to cap the downside risk of the two potential situations above. This is indeed possible. I will walk you through my approach.

When you accept a new job, a very healthy practice is to project out the opportunity over a period of time. I like to use increments of six months. What I recommend is you create a document for your job that predicts how the company has evolved, and you yourself have evolved over that time period. This document should ask the following questions:

#1 What should the trajectory of the company be at this time?

This can be represented by numbers, strategic initiatives, funding rounds, whatever makes sense for your mind. Actually, the more the better.

#2 What should my trajectory be at this time?

This can be represented in terms of what you accomplished, what responsibility you accumulated, how much you’re making, what you’ve learned. Again, the more the better.

Okay, so when you join the company, you write this document for let’s say six months, 12 months, and 18 months into the job. When those milestones occur, reflect back on this document and ask the following questions:

#1 Is the company on track?

Predictions are hard, of course, but being on track is great, being ahead of track is awesome, and being off track may be a cause for concern.

#2 Am I on track?

It’s almost as important to ask if your trajectory is on track. Are you learning what you thought you would, accomplishing what you thought you would, making as much as you thought, accumulating the responsibility you hoped for? All of that should be addressed.

If the answer to both of these questions is on track or ahead of track, amazing. You should feel confident continuing to work at the company. If either of these questions is no, however, you need to ask yourself two additional questions.

#1 Can it get back on track?

Let’s say the company is off track. Do you believe in a reasonable plan to get back on track. Was it a one time setback, or are we too far off course to hit the objectives you initially wrote? Similarly for yourself. If only one of the answers above was no, it creates different implications. A fast growing company, but not growing yourself creates a free rider problem for your career. A company where you’re growing yourself, but the company is off target may mean all you’re learning won’t be valued by the market if the company doesn’t end up doing well.

#2 If not, am I comfortable with the new track?

If you’re not on track and don’t feel you can get back on track, you have to ask if you’re comfortable with the new track. This is common. You may have set to high a goal, but things are still objectively going well. That’s fine. You do want to make sure you’re not justifying a mediocre or bad situation because it makes you uncomfortable.

If you follow this process, it should let you know if the opportunity you initially thought was worthwhile isn’t there. The key is when you learn this that you don’t continue to stay. If the company and/or yourself on not on track, you don’t expect to get it on track, and you’re not comfortable with the track, you should find a new job. As long as you change jobs when when you reflect every six months and see this, the risk is mitigated. The real risk is staying with a company a long time that is off track for itself and your career, with no way of getting back on, and it’s sacrificing your potential. Those are the only real career mistakes. So, go ahead and take that new job. But use this framework to be honest with yourself about whether it’s working out or not. And if it’s not, find a new one.

Currently listening to Between Two Selves by Octa Octa.

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