✨ How to Use Career Seasons to Support Your Ideal Life

Welcome to the 70 new subscribers to Going Places- I’m so happy you’re here!

If you’re like me, you grew up with a framework for life that was centered around clear milestones: graduate from school, land a stable job, climb the career ladder, and eventually retire.

We were taught to set one big career goal and relentlessly pursue it, often at the expense of our personal lives and broader aspirations.

But what if, instead of planning your life around one career goal, you reverse-engineered your career choices based on your life goals?

Imagine prioritizing what truly matters to you—be it family, travel, creative pursuits, or personal growth—and making career decisions that align with those values.

This shift in perspective can lead to a more fulfilling and balanced life, where your career supports your life goals rather than the other way around.

With the rise of portfolio careers and side hustles, the one-track career timeline is quickly becoming as retro as the peplum tops I wore to my first internship.

The future of work is diverse and multi-dimensional, with room to flex your career criteria to better suit your needs as they change from life stage to life stage.

Here’s how I’ve used a “seasons” approach to my career trajectory that helped me cultivate the life experiences I really wanted.

*You’ll see in my examples below that I’ve never had children or elderly parents to support, nor a serious partner’s needs to factor in (this can be seen as both a blessing and something I’ve missed out on, but that’s a subject for another issue)! 

Season 1: “The Entry-Level Girlboss”

What I Needed in Life: 

✅ A sense of professional purpose to apply myself to, having just graduated college

✅ A strong introduction to business savvy & corporate politics

How I Used My Career to Support That:

When given the choice between a “chill” entry-level job at a children’s education company and a much more dynamic, fast-paced assistant role at a media empire, I chose the latter. With virtually zero other responsibilities at 22, I wanted my job to be a focal point of my life, with daily opportunities to learn and expand as much as possible. Diving into the deep end & rising to the challenge fresh out of the gate accelerated my career much faster than the more relaxed job ever could have.

Season 2: “The SF Tech Girlie”

What I Needed in Life:

✅ The chance to keep “trying on” cities other than NYC

✅ A significant salary bump $$$

How I Used My Career to Support That:

After grad school in London, I was hungry to experience life in another big city that I might be able to call home. And, after grad school, I wanted to make way more money than where I’d left off in my Coordinator role. So I set my sights on Silicon Valley, having specifically done my graduate research on L&D in tech startups. The result? I finished my grad program in September, moved in with my parents while applying to all kinds of HR roles in San Francisco, and started my role at Stitch Fix in January with a base salary 3x my NYC salary (honestly, this says more about my media salary than it does about my tech salary)!

Season 3: “The Bridge Job”

What I Needed in Life: 

✅ Income to support my lifestyle while I fine-tuned my business idea

✅ Move back to New York/ New Jersey after 5 years away

How I Used My Career to Support That:

A bridge job can be a logical step when your career pivot is a little more complex than moving straight into the exact role you’re interested in (be it another corporate job or starting your own business). Maybe you know where you want to go next, but you need more experience, time, or savings before you can get hired or take that leap. In the summer of 2020, I knew it was time to get serious about being my own boss, but I didn’t want to dramatically shrink my expenses or lifestyle- yet. So, I got a job that fulfilled my financial needs and hustled on nights & weekends to prep for the leap.

Season 4: “The Solo Entrepreneur”

What I Needed in Life: 

✅ Go full-send on finally building my own business & brand

✅ A chance to experiment with time freedom and flexibility 

How I Used My Career to Support That:

By the time I gave notice at my bridge job, my career coaching business was in full swing. That meant that I’d reached a point where both of my jobs- corporate & coaching- were starting to suffer from splitting my energy between the two. The time was now, so I leapt and spent the next 3 years giving entrepreneurship my all. 

Season 5: “The Corporate U-Turn”

What I Needed in Life: 

✅ Coworkers

✅ Consistent schedule

✅ Time to regulate my nervous system

How I Used My Career to Support That:

After 2.5 years of solopreneurship, I reached a point in early 2023 where my business was making me really unhappy. Specifically: very, very lonely. I decided that working & living by myself wasn’t a healthy recipe at that point in my life, so I made the- somewhat taboo- choice to go back to a 9-5. This choice gave me the mental space to recover from burnout, log off at a predictable time most days, and work with other people everyday.

📍We are Here → Season 6: “The Portfolio Career”

What I Need in Life:

✅ A foundation for wealth-building through multiple income streams

✅ Opportunity to grow my personal brand & really start making my mark

✅ Freedom to answer, “What do you do?” in 4 different ways that feel true to me

How I’m Using My Career to Support That:

I cannot be defined by one job title anymore. “Career coach” leaves out the fact that I’m a fantastic public speaker, on-camera creative, and savvy strategist for B2B partners. So, I start everyday with the conscious decision to divide my time, energy, and income between several “part-time” projects instead of one all-encompassing “full-time” job. (The quotation marks are necessary, because I often work more hours a week now than I did with a FT gig). Is it confusing to some people? Sure. But the ones that get it, get it, and I’m certain everyone else will have no choice but to understand it as our disillusion with the “stable 9-5” keeps growing.

Reply to this email and tell me:

What would you title this “season” of your career?

This week’s question comes from Ali over on Instagram. She writes:

Cheers to building that personal brand! You’ll probably find your first speaking opportunities by reaching out to your warm network. These gigs will likely unpaid— but you need experience to get experience! So, look for openings to raise your hand, suggest a 30min workshop or training you’re qualified to deliver, practice, and build your speaking portfolio. That's how it works. Once you have enough unpaid experience, you’ll be able to choose the topics you love to speak about and those that don’t excite you as much. With that self-awareness, you can start pitching one or two “signature” sessions to aligned partners, and start asking for compensation!

Love the newsletter but want more? Did you know I put together an entire course called Pivot with Purpose? Think of it like a supercharged version of all the best content from this newsletter, tailored to help you nail your career goals.