Career Seasons: Choosing a Job Based on the Lifestyle You Want - Deepstash
Career Seasons: Choosing a Job Based on the Lifestyle You Want

Career Seasons: Choosing a Job Based on the Lifestyle You Want

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Different Points = Different Wants

Different Points = Different Wants

At different points in our lives, we want different kinds of jobs:

  • Growth point: When we prioritize learning and earning more — and we’re willing to put in the time
  • Lifestyle point: When we want to prioritize our time outside work, such as taking care of family
  • Reinvention pointWhen we want to completely reinvent ourselves, including the role and even industry we work in


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Dream Job: To Each His Own

Whenever Ramit Sethi, author of I Will Teach You To Be Rich, asked people what they wanted from a ”dream job”, one of the most striking things about their answers was how different they were.

Some people wanted to step back into their career full time after a hiatus. Some wanted to be able to spend more time with young kids. Some wanted to pursue meaningful work in another industry.

All Dream Jobs. All completely different!


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Career Advice: To All The Same

But, then, as well as now, if these people ask for help with how to reach their Dream Jobs, the common answers are all the same:

“Just follow your passion!”

“Just be thankful you have a job!”

“Just do good work and you’ll be rewarded eventually.”

(Have you noticed how so much bad advice starts with “just”?)

Our career goals aren’t generic and one-size-fits-all. So why is all career advice generic and one-size-fits-all? Why are the tactics we use — like surfing job boards and shotgunning out resumes — so generic?


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Introducing “Career Seasons”

We all go through different phases in each of our careers. Some of us are early in our careers, looking to grow and soak up knowledge. Sometimes we want to downshift, or prioritize family. And sometimes we want to reinvent ourselves entirely.

Ramit Sethi calls these different phases “Career Seasons.” 

Just like the seasons throughout the year, they’re natural. They change over time. And you may cycle through them more than once.

“Your Season has profound implications for the jobs you look for and even the way you search for your job.


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The “Growth” Season

Most of us started in this Season early in our careers. Some of us are still in it! In the Growth Season, we’re motivated by moving up the career ladder and making more money. We’re willing to put the time in and we don’t mind working hard. 

Here’s a quote from someone that instantly tells you that they’re in the Growth Season. 

“I feel like I’m falling behind compared to my peers. They’re moving on to senior management titles, director titles. I’m seeing everyone else have upgraded titles, so I say, ‘I want it too.’”


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The “Lifestyle” Season

People in the Lifestyle Season still value their work and career, but they also have other equally important goals. Here’s a classic quote describing the Lifestyle Season:

“I want to spend as much time with my kids as I can. I do not want to work 60 hours a week anymore.”

Notice these phrases, which instantly tip us off to the Lifestyle Season: “Flexibility” (or “flexible schedule”), “downshift,” or “family.” You may think about work/life balance if you’re going into a Lifestyle Season.


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The “Reinvention” Season

Reinvention Season describes people who want to totally reimagine and change the course of their career, usually by switching industries. Imagine a lawyer who wants to leave her firm and join a start-up.

Here’s a quote from someone in Reinvention Season: 

“I have 12 years of financial sales experience, but I feel pigeonholed onto a sales track and don’t enjoy the work. I’ve always wanted to transition to a computer science field, but have no formal experience.”

You’ll hear typical phrases like “fresh start” to describe this Season.


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A Few Notes About Seasons

1. No Season is better than the others.

No judgment against any Season — it’s your Season. You choose what’s right for you now.

Think of the previous quotes. For some, one or more of them sounds terrible. For others, this is exactly where they are.

That’s the point! The right Career Season sounds exactly right to you… and wrong to everyone else. 



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A Few Notes About Seasons

2. We naturally move in and out of Career Seasons as we get older.

Just like actual seasons. While it makes sense to want all of these things to happen simultaneously, some things are just more appropriate for certain Seasons. You can choose the right Season for you — but you can only pick one.

For example, it’s very difficult to embrace the Growth Season and the Lifestyle Season at the same time. Think of what each one asks of you or what you ask of it. So, you can try, yes… but doing so makes it difficult to make any meaningful progress in either. 


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A Few Notes About Seasons

3. Finally, EVEN if you feel like you could be in multiple Seasons, you NEED to pick ONE.

This is hard, especially for top performers who like to go above and beyond. But you will find that trying to do more than one at a time means not doing your best at either.

(And Ramit Sethi knows he is repeating here, but he’s repeating this because it’s so important.


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“An idea is something that won’t work unless you do.” - Thomas A. Edison


Ramit Sethi argues that, just like there are seasons in our life, there are - and must be - seasons in our career and that without understanding “our” Career Season, we can’t and won’t find a job that’s perfectly made for us.

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