The Career Transition Hill of Anxiety

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Throughout my career I've been through three major career transitions. In each of these transitions, I've sought out spending time with others also in transition. In some of these transitions, I've made great choices. In others, bad choices. I've also seen others do the same.

One thing I've noticed is what I call The Transition Hill of Anxiety. It helps explain where good and bad choices are made. Let's think about this as a graph:

  • Y-Axis: The amount of anxiety about what we should do next.

  • X-Axis: The amount of time we have been in transition.

Career Transition Hill.png

Within this I think there are four stages:

  1. The Optionality High

    We leave our gig. At first, we have low anxiety. It feels incredible. "I can do anything!" The sea of options creates a ton of excitement.

  2. The Peak of Anxiety

    Some time passes. But our anxiety about finding what is next increases quickly. I think this happens for a few reasons:

    • The sea of options goes from creating excitement to creating anxiety. Making career decisions is hard. Those hard decisions create anxiety. Our inability to make the decision easily creates even more anxiety.

    • Operating in a high-growth tech company requires to be always-on. We need to direct that energy somewhere. When we don't have a place to direct that energy, that turns into anxiety.

    • The reality of no income (if you are taking time off) starts to become real, no matter how much you planned on it.

    • The "amazing" ideas we had before deciding to leave see some cold hard truth and don't look as great as they did before.

    The problem is, a lot of career decisions are made at The Peak of Anxiety and where most of the bad decisions occur. The anxiety rushes us into roles or companies that were not a fit.

  3. The Trough of Relaxation

    If you are able to wait long enough you eventually push through the Peak of Anxiety and come back down to the Trough of Relaxation. This is where actual recharging takes place. Not in The Optionality High.

  4. The Field of Good Decisions

    Finally, the level of anxiety starts to creep up again, but more slowly than during the Peak of Anxiety. This time the stress takes the form of good stress. It is saying "I'm recharged, had time to consider a lot of options, and ready to get back into action." This is where I've made my best career decisions (HubSpot and Reforge) and seen others do the same.

Unfortunately, a lot of people aren't in a position to take the time needed to get past the Peak of Anxiety. That is why we created the Executive-In-Residence and Operator-In-Residence programs at Reforge.

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