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My $250,000 decision ​
- The hidden downside of being “the expert”
- The Student–Teacher Loop (and why you need to embrace it)
- 5 ways to become a student again in 2026
♟️ MY TURN:
Spoiler alert: I am deciding to give up $250k this year.
Let me explain....
I’ve spent the last 3 years building a portfolio career of income streams and teaching others to do so as well - and it’s something I’m so proud of.
- I’ve grown this newsletter to over 80k subscribers.
- Published a bestselling book.
- Grew my MRR to $50k with community, courses and content deals.
But something shifted inside of me.
After years of being the teacher…..
I want to be a student again.
I want to learn more.
I want to see what I don't know.
I want to try new things.
And this is hard to do when you are spending the majority of your time teaching what you already know.
At the end of last year I made the decision to sunset my Office Hours community and this year I’ve scaled back on courses and webinars where there is a big emphasis on teaching.
That’s $15-25k a month I’m actively choosing to let go of.
Why?
In my book, Toxic Grit, I shared an exercise I do every year to set the intentions. It’s called the perfect day exercise and you can check it out in the Toxic Grit workbook here.
This year when I pictured my perfect day?
I saw:
- Launching a new brand, in a new industry [that I’m the CMO of, not the face]
- Researching and writing on a new topic
- More white space to learn, play and grow (and fail)
The Student–Teacher Loop
Here’s the pattern I see in most ambitious careers:
- Student – You know nothing, so you learn fast.
- Teacher – You turn what you’ve learned into leadership or even a portfolio career of content, courses, leadership, and status. People start asking, “How did you do it?” and you build a business answering that question.
- Operator – You optimize what you’ve built. Systems, SOPs, automation. It’s efficient, profitable and repeatable.
My hot take: Careers should be a loop NOT a ladder.
There is a season to be at the top of the field.
Standing in your knowledge, wisdom and expertise.
Then there will come a point where things feel mundane or, perhaps, stifling.
This is the signal that it’s time to be a student again.
But most people view phase 2 or phase 3 as the final destination and not just the next stop on the loop.
And this can cause us to feel stuck or disconnected from your work.
The Neuroscience of Novelty
The human brain is designed to pursue novelty.
As cavemen that likely kept us alive as we were constantly on alert for things that were changing to protect ourselves from predators.
It’s also why the video game industry is projected to exceed $600b by 2030.
Our brains seek out novelty.
So it makes sense that when you become known for something and a teacher of that something….you might start to seek out the next thing.
And, if I’m being honest, I think the world needs to move away from certainty in any stance to curiosity in all things. Beliefs held so tightly as certain are dangerous.
Expertise is “overrated”
When I worked for a celebrity wedding planner who had a reality TV show, he was asked why he still planned everyday weddings when he was already seen as the celebrity wedding expert.
His reply?
“What was cool last year will be uncool next year and I need to understand what is happening across the industry”
A few other reasons I love the student-teacher career loop:
- Keeps you adaptive: The more knowledge a person has in a field, the more difficult it can be for them to adapt when the rules change. I don’t want to feel so rigid in my beliefs.
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- Keeps you humble: Expertise can lead to being overconfident in one's ability to solve problems. I want to always seek opportunities to learn from those around me.
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- Limits mental shortcuts: Expertise often creates mental shortcuts that can turn into blind spots. We don’t know what we don’t know.
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- Keeps you current: In fields that change rapidly, like marketing, expertise based on past successes can quickly become obsolete. When I became a marketers, social media was just Facebook. Discovery was SEO. And look at where we are now.
So I’m choosing to not be an expert this year.
I’m choosing to be a student.
This requires space and a shift in my mindset.
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♟️ YOUR TURN:
People call this “beginner’s mindset,” but I think it’s more intentional than that.
It’s not about pretending you don’t know anything.
I still have a 20 year career in marketing.
I still wrote a best selling book.
I still built a $50k MRR business from scratch.
It is about choosing rooms, projects, and identities that demand you grow.
If you feel stuck heading into 2026, use that as data.
It might be your brain telling you, “We’ve outgrown this level.”
Here are 5 ways to be a student again in 2026:
1. At Work: Take on one thing you’re not the expert in.
- Volunteer for a project where you are clearly not the most qualified person in the room.
- Level up your own role: ask smart questions, document what you’re learning, and ship something you’re proud of.
- Measure success not by praise, but by how often you thought, “I have no idea how to do this… yet.”
2. At Home: Let someone else be the teacher.
- Ask your kids or partner to teach you something they care about - a game, a sport, a hobby, a fandom. Take it seriously. Learn it well enough to hold a real conversation about it.
- Get curious about your partner. They are growing and changing every day so re-enroll in getting to know them!
3. With Friends: Start a “study dinner.”
- Once a quarter, host a dinner where everyone brings one thing they’re learning about….. an article, a book, a podcast, an experiment.
4. Personally:
- Money, hormones, geopolitics, AI, design… pick something that genuinely intrigues you or overwhelms you.
- Give it 20 minutes a day for 30 days. Read, take notes, watch lectures. (No monetization plan. No content strategy. Just put in the curiosity reps.)
5. With Your Health:
- Work with a trainer, a therapist, a coach, or a specialist.
- For 8 weeks, commit to being the most coachable version of yourself: do what they say, even when it feels inconvenient.
- Notice how uncomfortable it is to not be in charge….. and how much growth lives there.
If your 2025 was all about teaching, optimizing, and squeezing more from what you already know, maybe 2026 is your year to re-enroll……in your life.
Where, in your life, are you wanting to be a student again?