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- Your Career Path Is Broken
If you started thinking about your future career today, what would your plan look like?
If you're drawing a blank—or defaulting to job titles, big-name companies, or chasing a higher salary—you're not alone. But you're also headed for the same trap that keeps so many talented people stuck and unsatisfied.
In this week’s newsletter, I’ll walk you through 8 questions that will completely reshape how you think about your career path.
These aren't theoretical ideas. I've used them with coaching clients to help them shift from drifting to designing work that actually fits them. By the end, you’ll understand why conventional career advice leaves so many people frustrated—and what to do instead.
The Default Path Trap: Why Most Career Advice Fails You
Most people are following someone else’s blueprint for their life. That’s the core of the problem.
Society hands you the “default path” early on:
Go to school 🏫 → Get a stable job 👨💼 → Climb the ladder 🪜→ Retire 👴
That worked for your parents and grandparents in a world where people stayed with one company for decades.
But that world no longer exists.
Companies lay off workers regularly, skills become outdated faster than ever, and career stability is often a myth.
Even the advice we get hasn’t evolved. It’s mostly about:
How to get promoted 📈
How to ask for more money 💸
How to make your résumé stand out 📝
But here’s the question almost no one asks:
“What do you actually want?”
The default path doesn’t care what you want. It only cares about moving you through a predefined sequence.
As a result, people chase promotions, titles, and raises—not because they’re meaningful, but because they’ve been told that’s what success looks like.
The real problem isn’t finding a job, it’s finding the right work that aligns with who you are.
And that’s where most career advice fails: it focuses on external validation instead of internal alignment.
That’s how “successful” people end up quietly miserable—because they’re living out someone else’s definition of success.
Rebuilding Your Career: The 8 Questions That Actually Matter
Let’s walk through the eight questions that form the foundation of a career that actually fits you.
1. What do you want to do?
Know what you want? Stop here & go after it.
Some people have their minds made up & just need a roadmap. If that’s you, remember to focus on the goal & not get stuck on the path.
Not you? That’s OK & why questions 2-8 exist.
2. What skills do you want to grow?
“I need to know everything to get this job”
Not true. There may be some basic requirements, but consider that you will also want to take away something from a job more than just a paycheck. Your career should be a learning engine.
If it’s not teaching you anything new, it’s not taking you anywhere.
3. What level of visibility do you want?
Sit in a cube or be in front of the world?
Not everyone needs to be the face of a company. Some only want a career that challenges them & where they can make a difference from their desk
Identify what you’re looking for & make it known.
4. Who’s already doing what you want to do?
Your network is your net worth.
Reach out to people who are doing something you think is exciting or interesting. Learn from them while also making your future intentions known
Ask for more contacts & make a good impression
5. What problems can your current skills solve?
Here’s the biggest unlock:Careers are built by solving problems—not chasing roles.
Every business has problems & needs help. There are times when you can bring your skill set & craft a job based on how you can help solve a problem
Fun Fact: At one point in my career, I made up my position. Saw a need and proposed a way (and position) to go solve it. Now someone has to be interviewed to get that job
Be willing to think outside the box & create opportunities for yourself
6. What do you enjoy—and what drains you?
Ignore this and you’re guaranteed to burn out.
Never discount finding a way to do what you love. If you have a true passion for something that makes you unbelievably happy, stick with it! Career happiness will take you so much further.
Consider if that exists at your current job or not
7. What kind of work-life balance do you want?
Let’s be honest, some jobs just demand more
You need to consider the impact a job will have on your overall Life Balance. Write down what your “non-negotiables” are & stick to them
Search for “Wheel of Life” for a good perspective
8. What growth do you want next?
Look beyond the job title, a great job isn’t great if it becomes a dead end
In chess, you always need to think a few steps ahead. Career choices are similar. You don’t need to know EXACTLY what you do, but it should put you on a favorable growth path.
This includes: Business, Personal, & Financial
For some reason people like to avoid the money topic, but for many it’s one of the most important. Be honest and realistic with yourself here. Understand what it means for your future and what you need to work on to grow
Conclusion: Stop Waiting for Permission
The difference between a stagnant career and one that thrives comes down to mindset. One waits for opportunities. The other creates them.
If you’ve been told your whole life to “fix your weaknesses,” here’s a different take:
In the real world, you don’t need a tutor—you need a coach to multiply your strengths, and a team to fill your gaps.
Start with one action: Write down this question—
“What do I actually want?”
Use it to filter every opportunity from here on out.
This isn’t about being reckless. It’s about being intentional.
Because the truth is:
Your career is too important to leave on autopilot.
A few tools, studies, and ideas that align perfectly with this week's topic:
✅ [Book 📚] The Pathless Path by Paul Millard — A fantastic read for anyone redefining career success on their own terms.
✅ [Tool 🔧] “Wheel of Life” Assessment — A quick way to evaluate how balanced your current life really is.
Here’s a free version you can try. I’ll be doing a video on this soon too
If you enjoyed this issue, make sure you’re subscribed to keep getting real, practical advice you can actually use.
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Got a friend who's stuck in their career? Forward this to them.
It might be the spark they need.