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

I’d like to introduce the concept of Career Seasons to you — which will help you find a job that’s perfect for you in this season of your life.

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

• Growth: When we prioritize learning and earning more — and we’re willing to put in the time

• Lifestyle: When we want to prioritize our time outside work, such as taking care of family

• Reinvention: When we want to completely reinvent ourselves, including the role and even industry we work in

Without understanding your Career Season, how can you find a job that’s perfectly made for you?

Here’s how we discovered this concept.

Whenever I ask people what they want from a Dream Job, one of the most striking things about their answers is how DIFFERENT they are.

Some examples I’ve received:

• “I’ve worked part-time for a couple of years whilst my family needed me. Now I’m going back to complete my Master’s and stepping back onto the career ladder full time.”

• “My kids are toddler age and I want to be available for them during this time of growth. Just having time to spend with them is a priority for me.”

• “I have been searching for a new job for some time, but this would include a career change. The older I get, the more I want to be doing the job I have always dreamed of.”

Notice how different all of these answers are! 

Stepping back into their career full time after a hiatus. Spending more time with young kids. Pursuing meaningful work in another industry. All Dream Jobs. All completely different!

But 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?

I think it’s time to change this.

Hence, the concept of Career Seasons.

For example, the person who wants more time with their kids may want to look at a job that’s 100% remote for a flexible schedule. 

What if someone wanted to switch careers? They should do their homework — like talking to experts who made a similar industry switch — to find out which skills are transferable and how to communicate that on their resume and in interviews. (It can be done.)

Or what about the person who really wants to hit the 6-figure mark? They should look for roles with a lot of room to grow and demonstrated promotions. And they should be willing to put the hours in.

This makes sense — and yet very few people do it. Who teaches us how to tailor our job search to our unique needs?

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.

I call 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. 

I want to spend some time here helping you determine your Season — and showing you other people like you — so you can narrow down your focus. This will save you hours and hours in the process.

Let’s go over each Season, with real examples. 

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. 

This was me in my 20s. I worked really hard and I wanted to soak up everything I could. I was motivated by recognition, growth, and learning. And I didn’t care how long I had to work.

Here’s a real quote from someone that instantly tells me 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.’”

For some of you, this sounds terrible. For others, this is EXACTLY where you are.

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

People in the Growth Season want more experience and more money…and they’re willing to work for it.

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.

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. I love these stories.

Here’s a real 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.

Now, 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.

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. One of the things I show you how to do is 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. You can try, yes…but doing so makes it difficult to make any MEANINGFUL progress in either. 

Think about it — could you ski during summer? No, there’s a season for that. Same thing here. There’s a Season for accelerating our career and a Season for more leisure time. It just depends on what we want, and therefore what Season we’re in.

I knew very early on in my career, before I Will Teach You To Be Rich took off, I was in the Growth Season, focusing on fast-tracking my career. I was pushing hard at a start-up I co-founded and writing the I Will Teach You To Be Rich book at night and on weekends.

These days, I still work hard, but I also prioritize traveling for many weeks at a time (at least I did before COVID hit, and I’m looking forward to doing it again soon). So I find myself in Lifestyle Season. That may change later.

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. (I’m repeating this because it’s so important.)

Which Season do you think you’re in? Let me know on Twitter.

This post on TessMore Finance: Career Seasons: Choosing a Role Based on the Lifestyle You Want was also published on: I Will Teach You To Be Rich.

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