Cool jobs vs. Not so cool jobs

Jun 18, 2021

When I started searching for a job in July 2020 I lacked a concrete vision of what I was looking for. I tried being authentically josh in how I wrote cover letters and formatted my resume, but it wasn’t connecting, which resulted in a low interview percentage. I quickly became discouraged. By September, I compromised and started working with a bunch of recruiters on LinkedIn.

My compromise led to success, i.e. two mediocre job offers. All I needed to do now was internally justify my compromise and accept one of the offers I had gotten. They were better than my current job, isn’t that good enough? These were the thoughts that rolled through my mind. My lizard brain was working overtime, justifying away the things I had hoped for, while internally I was disappointed with both prospects.

I ended up accepting one of these offers and then bailed during the onboarding. My justification just couldn’t last through all the crazy agreements they wanted me to sign.

I learned that

Making decisions well is about making them ahead of time. In your job search, you need to define what you are looking for, or your emotions will take over, and you will likely regret where you end up.

What are your expectations for the next gig? What values do you want to share with your employer? What sort of IP agreements are you not willing to sign?

It’s worth thinking about.

Here is what I came up with last October as I restarted my search:

This list was helpful for two reasons:

1. It helped me find my Smallest Viable Market

Job searching is marketing and you are the product. If you focus on the companies that you jive with, you have more freedom to be yourself in how you apply. In turn, this freedom differentiates you from other applicants.

This is internally helpful because it takes the weight off of being the perfect candidate and helps you focus your energy on a few companies that you aspire to work with.

And externally it’s helpful because you want to be hired based on a connection (something you can control) rather than on weak metric like GPA (a race to the bottom that most people can’t win).

2. It put me on the hook and helped me hold my ground

Saying your goals out loud means that you can no longer internally justify compromise. You are putting yourself on the hook.

Job searching is serious business and is something you want to be held accountable for. It’s important. How much you make and who you spend 40 hours of your week with will have massive implications on your future.

We all know this internally, but many approach job searching without planning or strategy. The rejections will come. How are you going to hold your ground when they low-ball you an offer? How are you going to negotiate strongly when you just want to move on with your life?

I believe we hold our ground in life by making the decision ahead of our emotions. Jobs have big implications and big implications create big emotions. Being logical ahead of your emotional side can help you make a decision that you won’t regret 3 weeks later.

So you have a list? Use it!

In the following months, I reminded myself every week of what a “Cool Job” was. Being reminded of what I was after helped me choose where I was applying more deliberately, and as I got offers or moved through the process I rated companies based on my values.

This made it easy to decide where I wanted to go, and in retrospect, it helps me have no regrets when things are inevitably not perfect at Clearcover. I didn’t just wing the decision. It was calculated.

I would love to hear your thoughts on this method. What you would include? What are your strategies for not compromising? Feel free to DM me!

Till next week...

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