Many of my peers and I have latched onto the framework of a Five-Year Plan, whether it was reinforced through the high school-college-career pipeline or that old chestnut of an interview question, "Where do you see yourself in five years?"

In my opinion, a question that was meant to encourage us to develop a sense of vision and intentionality may have actually stunted our willingness to experiment and pivot. 

We became so committed to our meticulously planned futures that we lost our ability to try something without needing it to be The Thing™ for the rest of our lives.

And in a world where entire industries can be disrupted in a matter of months, where AI is reshaping job categories faster than we can update our LinkedIn profiles, where the "rules" of work change every few years... the Five-Year Plan is actively holding us back from our most agile, adaptable, and fulfilled selves.

So, what can we do instead?

Take it Back to Middle School Science Class

Do you remember the scientific method from grade school?

Start with a question.
Form a hypothesis.
Design an experiment.
Collect data.
Analyze results.
Draw conclusions.

The whole point wasn't to prove your hypothesis was right, but to learn something, regardless of the outcome. A "failed" experiment wasn't actually a failure, it was just information.

Somewhere between our playful adolescence and perfectly-planned adulthood, we forgot this.

We stopped treating our professional lives like experiments and started treating them like commitments we had to defend. Every job became a five-year statement of intent. Every pivot looked like admitting failure and starting again from scratch.

But what if we brought the experimental mindset back?

What if instead of asking "What's my five-year plan?" we asked "What's my five-month experiment?"

Why the 5-Year Plan Framework Is Too Outdated

Let's be honest about what's changed since the Five-Year Plan became career gospel:

🏃‍♀️ The pace of change has accelerated beyond recognition.

In 2020, who could have predicted that remote work would become the norm? That an entire generation would quit their jobs in what we'd call the Great Resignation? That ChatGPT would launch in late 2022 and fundamentally shift how we think about knowledge work?

We can barely predict what skills will be in demand 18 months from now, let alone five years. The career landscape is shifting beneath our feet constantly.

🏆 The old markers of "success" have lost meaning.

Previous generations could plan: stay at the company, get promoted to manager, VP, maybe C-suite. Buy the house. Collect the pension.

But only 6% of millennials say their primary career goal is to reach a leadership position. We've collectively shrugged off the corner office, and our paths are becoming less and less linear.

🎲 The cost of being wrong is too high.

When you commit to a Five-Year Plan, you're committing before you have enough information. You're betting your next half-decade on a hypothesis you haven't tested.

And when that plan doesn't work out— when the job isn't fulfilling, when the industry shifts, when you realize you chose it because you were good at it, not because you actually wanted it— you don't just feel disappointed. You feel like you failed. Like you wasted time you can't get back.

The Five-Year Plan mindset makes every course correction feel like a crisis.

Enter: The 5-Month Experiment

Here's what I'm proposing instead: treat your career like a series of experiments, not commitments.

Five months is long enough to:

• Learn something real

• Build a skill

• Test whether you actually enjoy something or just like the idea of it

• Gather real data, not just daydreams

But it's short enough that:

• You're not betting your entire future on it

• Failing, or not liking it, doesn't feel catastrophic

• You can pivot without the weight of a "wasted" multi-year investment

• You can try multiple things in the time it would take to execute one rigid plan

Those of us who will thrive in the next decade won't be the ones with the most ironclad plans.

We'll be the ones who are comfortable experimenting, iterating, and treating our career experiences like a laboratory instead of a locked-in trajectory.

A Starter Framework: Your First 5-Month Experiment

So you've been curious about something— freelancing, content creation, a career pivot, starting a business, going back to school— but you've been paralyzed by the commitment? By the pressure to make sure it works out?

Here's how to structure it as an experiment instead:

Month 1: The Hypothesis

• What are you curious about testing?

• What's your actual question? (Not "Will this be my forever career?" but "Do I enjoy the day-to-day of this work?" or "Can I build this skill while keeping my current job?")

• What would "success" look like for this experiment? (And remember: learning "this isn't for me" is a successful outcome)

Months 2-4: The Experiment

• Take one concrete action per week that moves you closer to testing your hypothesis

• This could be: taking a free course, doing freelance work on weekends, posting content 3x per week, informational interviews, shadowing someone, joining a new community

• Track what you're learning— skills, yes, and how you feel doing this work

• Give yourself permission to hate it. To love it. To feel confused. That's all data.

Month 5: The Analysis

• What did you learn about yourself?

• What surprised you?

• Based on what you now know (not what you thought you knew), what's the next logical experiment?

• Do you want to go deeper into this path, pivot to something adjacent, or close this chapter and test something else?

The key: You're just deciding your next move, not your entire future.

What This Actually Looks Like

Maybe your Five-Month Experiment is:

• Testing freelance copywriting on weekends while keeping your marketing job

• Launching a newsletter and committing to publishing weekly for five months

• Enrolling in a data analytics bootcamp and building one portfolio project

• Reaching out to five people in a field you're curious about and asking them what their day-to-day actually looks like

• Saying yes to a stretch project at work that scares you

• Starting a side business and seeing if you can get your first five clients

None of these require you to quit your job, burn it all down, or have it all figured out.

They just require you to start.

The Permission You're Waiting For

Repeat after me: “I don't need to know where this is going.”

You don't need to be sure it's going to work out.

You just need to be curious enough to run the experiment.

Because, in my opinion, the ones who are going to be the most fulfilled, the most adaptable, the most resilient in the years ahead are the ones who got comfortable not knowing, but exploring anyway.

So what's your next experiment?

What have you been curious about but too scared to fully commit to? What would change if you gave yourself permission to just test it for five months?

I want to know: reply to this email or leave a comment below with what your first experiment might be!

This week's question comes from Sarah, a nurse, on Instagram:

This is the exact reason I love the experiment framework!

Here's my rule of thumb: If you're exhausted by the work itself, that's a sign. If you're exhausted by the uncertainty, the learning curve, or the vulnerability of being new at something… that's just part of the experiment.

When I was building my coaching business, I loved the work: the conversations, the group dynamics, watching people gain clarity. But I was exhausted by the constant sales cycle, the content treadmill required to ~fill my pipeline~, and the isolation of being a team of one.

That exhaustion was data. It told me I wanted to shift from sales-focused content to reach-focused content, and eventually back to a role with a team (whether full-time or part-time).

So ask yourself: Am I tired of the work, or am I just tired of being a beginner?

If it's the former, you have your answer. If it's the latter, maybe give yourself one more month of the experiment.

Either way, it's all just information.

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.