Masterclass: 7 Ways People Get Stuck When Figuring Out Their Next Career Step
Buckle in, friends, because today, I have full on masterclass for you.
I’ve taken hundreds of hours of coaching and distilled down my absolute best insights — the MOST common problems my clients run into when they’re figuring out their next career step and the simplest, most actionable ways to solve them and get unstuck.
So save this, bookmark it, and come back to it again and again because this email is literally a comprehensive diagnostic and action planning tool for your entire job search and career change process.
Keep this guide in your pocket and every time you run into a problem — come here, diagnose it, do what I tell you to do, get unstuck, and then keep on moving.
Alright, let’s jump in.
Figuring out your next career step is not a complicated problem.
If you’re reading these words, I can guarantee that you’ve already solved harder, more complex problems than “What should my next job be?”
So why do people get so stuck and confused and spun out by this question?
The real issue is NOT that this is hard to figure out…but that people have emotional cobwebs clouding their problem-solving ability and keeping them stuck.
So here are the 7 most common ways people get stuck when they’re trying to figure out their next career step…
And simple, practical ways to unstick yourself today.
Stuck Point 1: You think you’ve made mistakes in your past career decisions.
In the past, you’ve thought carefully about which job to take…
You’ve sought advice, talked to people, and made a thoughtful, analytical decision that you believed was right at the time…
And then things didn’t turn out the way you expected. The job was bad. You didn’t like it as much as you thought you would. The people turned out to be terrible. etc. etc.
So now you’re making another change.
People get stuck when they look at their past and think: “I must be doing something wrong,” and lose faith in their own decision-making capabilities.
If you doubt your ability to make good career decisions, or you’re embarrassed or ashamed of the “mistakes” you’ve made in the past, it will keep you stuck.
You can’t figure this out if you don’t trust your own ability to figure this out.
So let me give you a different way to think about your past career decisions.
All those cycles of “I think this is it! Wait, never mind, I was wrong. Now I think it’s this! Wait, never mind, I was wrong”?
That’s your career journey going RIGHT.
Your career is not an intellectual problem that you figure out once and then you just “set it and forget it” until you retire.
Your career is constant adjustment in the face of constant change and new data.
You change. Your priorities shift. You learn new things about yourself. New interests and values arise.
The world changes. Pandemics happen. Markets shift. New technologies develop.
The people you work for change. Companies reorganize. Goals and objectives shift. People leave, and new people arrive.
Every career decision in your past represents your best hypothesis, for that situation, given the data you had at the time.
And every time you made a change, that was you updating your hypotheses based on new data, for a new situation.
You haven’t been making mistakes.
You’ve been conducting a years-long hypothesis-testing, data-gathering experiment — and you’ve only gotten better, stronger, and smarter through it all.
All those so-called mistakes aren’t a sign you can’t trust yourself.
They are concrete learnings you’ve gained through robust experiments — and they’re the exact reason you CAN trust yourself.
So here’s what I want you to do. Rewrite the story. All those things that you think are “pitfalls” and “past mistakes”?
What specifically did you learn from them? How do they inform your thinking now? How are you better equipped to find your next job now than you were before?
Change the way you feel about your past, and you’ll be well on your way to figuring out your future.
Stuck Point 2: You think you don’t know what you want.
“I don’t know what I want” is a bold-faced lie.
You DO know what you want. If I started suggesting different career paths to you, you’d instantly be able to tell me which sound good and which sound terrible. Your internal compass is alive and well.
If you want more clarity on what you want, go do these five exercises OR literally just take a guess. If you DID know what you wanted, what would it be?
I guarantee that the answer is already in your brain.
99.9% of the time, what people need is not more CLARITY on what they want but more COURAGE to own what they already know they want.
The real blocker here isn’t that you don’t know…but that you think you shouldn’t want what you want. “It’s silly. It’s not practical. Nobody does that. It’s too big. It’s too small. I’ll fail at it. It’s not what you’re supposed to do.”
Those are all issues you can tackle and address…
…but you can’t address them if you hide behind the lie that you don’t know what you want.
So let me give you two practical ways to OWN what you want.
First, address your brain’s objections.
On paper, or out loud by talking to someone.
“It’s silly” — How is NOT silly?
“Not practical” — How IS it practical?
“Nobody does that” — Who DOES do that?
Build the logical case for why what you want makes total sense.
Second, find people like you.
If you’re the only one you know who wants what you want, you’ll feel like a crazy person.
This isn’t a moral failing on your part. The Asch conformity experiments show how people bow down to group pressure even when the group is saying something obviously, factually wrong.
No matter how sophisticated and “evolved” you are, there’s a part of your animal brain that just feels really uncomfortable when you’re the ONLY one in a group that thinks a certain way.
You don’t have to fight against this part of yourself. Just go find other people like you. Remove the “social pressure” element from your thinking, just for a few hours, and see what’s left.
Stuck Point 3: You think you’re not qualified to get what you want.
You’re clear on what you want…and you’re 100% certain no one would ever hire you for that job.
Your resume doesn’t look right. You don’t have the right experience. The hiring market is so competitive. Etc. etc.
Believing this story is a surefire way to get stuck.
Because if you know what you want…
But you’re convinced you can’t get it…
What are your options?
Downsize your dreams and live in grumpy resentment, of course.
Don’t do that.
Instead, let me give you two ways to build your belief that you ARE qualified to get what you want.
First, look to your processes, not your outcomes.
Let’s say you want to get into investing, but you’ve never closed any deals before.
Your brain will tell you: You haven’t done it, therefore you’re not qualified.
This is an outcome-based approach to qualifications — if you’ve delivered these exact results before, you’re ready! If not, do something else.
But let me make a bold assertion:
Nobody is hired for their past results. Everyone is hired for their current & future processes.
If a fund hires a rockstar investor who’s closed 100 deals in the past, they don’t get any tangible value from the PAST deals she’s closed. Those deals were all made for someone else.
The fund looks at her past 100 deals and assumes: She must have a great process for identifying, structuring, and closing deals. If she applies her process while working for us, she’ll create value for us too.
The fund is hiring her for her current and future process. The past outcomes are just a proxy for “This person has a good process.”
So even if you haven’t delivered the exact outcomes this job will ask you to deliver, dig into your processes.
How do you approach problems, break things down, prioritize, analyze, synthesize, and get from A to Z?
How can you build the case for yourself that you ARE qualified, based on your processes?
Second, get out of the classroom model of success.
The classroom model of success is this:
Get the lesson ➡️ Study hard ➡️ Take the test
If you get an A on the test, that means you’re successful.
The real world model of success is this:
Take the test ➡️ Get the lesson ➡️ Study hard
There’s no study plan or syllabus for the real world. You can get degrees and qualifications and certifications — but the real learning happens through doing.
Which means the most successful people aren’t the ones that study the most. They’re the ones that are brave enough to “take a lot of tests” they’re not fully prepared for so they can learn a lot of lessons.
Feeling unqualified for what you want? Good. That’s the point.
The only way to grow into who you want to be is to start doing stuff you’re not 100% sure how to do.
You’re on the right track.
Stuck Point 4: You think no one wants what you have to offer.
This comes up for people when they want to bring their existing skillset into a new area.
You’re changing industries, changing functions, going from a corporate job to your own business — or just trying to figure out what the heck you want to do next.
You know you’re good at what you do. The problem is that you’re used to serving your “current customer base” and you’re not sure that your “new customers” will want anything to do with you.
This fear keeps people stuck because they’re afraid of rejection and so they just don’t put themselves out there or test the waters at all.
But if you don’t put yourself out there, you have no option but to keep working for the same kind of companies in the same kinds of jobs you’ve already been doing — and you don’t want to do that anymore!
So how do you unstick yourself? Stop making it so personal.
It’s not about you. Think about it like a strategy project.
Imagine if someone handed you a random product and told you to go figure out the business strategy for making this product successful and profitable.
You’d probably go figure out:
What kinds of problems is this product good at solving? What is this product good at doing? What is not as useful for?
From all those problems, which are high-priority problems that people would pay a lot of money to solve?
What kinds of people have those high-priority problems that are super well-solved by your product? Where do they hang out? How can you go reach them?
And you wouldn’t be stressed or nervous or apologetic about figuring all this out because it’s not personal. It’s just a strategy project.
You can take the same approach to your career.
You have a product. That’s your skillset, your processes, your experience and expertise, and the unique way that you solve problems.
Now you just need to figure out what kinds of problems that product is well-suited to solve and which of those problems are really high-priority — aka people will happily pay you a lot of of money to solve them.
And would you go into a strategy meeting with just ONE option to present?
No! You’d present a variety of different options and strategies!
Do the same thing for yourself. Generate a BUNCH of options. Talk to people. Do research. Get creative. Find options you didn’t know existed.
It’s a big, big world out there, with whole industries built around things you’ve never heard of.
And in that big world are many perfect customers for You, The Product. You just have to find them.
Stuck Point 5: You think you can’t have it all.
You’re clear on what you want. You know you’re qualified to do it. You know there’s demand for what you offer.
BUT you can’t have it all — or so says your brain.
You’ll have to take a pay cut. You’ll have to give up work-life balance. You’ll have to move to a location you don’t like. Aka, You have to give something up to get what you want.
This thought will keep you stuck if you treat it as a fact of life that you have to solve around…
…rather than as a hypothesis that you rigorously try to disprove before you accept it.
99% of the time, people think “I can’t have it all” and then get to work reconciling themselves to this sad “fact.”
I don’t want you to do that. I want you to hear yourself say “I can’t have it all” and get to work proving that FALSE.
How CAN you have it all? Without the pay cut? While being home for dinner every day? From the city you want to be in?
Point your brain at SOLVING the problem, not at accepting it as a given.
This way, even if you ultimately decide that you DO want to accept certain tradeoffs… (And notice I said WANT to, not HAVE to.)
You will be much happier doing so when you’ve thoroughly explored all the options and you’re choosing this way forward, not being forced into it.
Tradeoffs only keep you stuck when you accept them as a sad fact of life without testing them and truly exploring and choosing between all the possibilities.
Stuck Point 6: You try to figure it out by thinking, not doing.
You broadly know what you want. You’ve come up with some options for what you could do next.
And now you’re stuck. You’re making endless pro/con lists. You’ve asked everyone what they think. You pick something and then change your mind two hours later.
You’re waiting for the lightning bolt of clarity to strike…and it’s just not coming.
If this is you, you need to figure it out by doing, not thinking.
No more theoretical exercises and hypothetical discussions. You need to gather real-world data.
Here’s how. First, rank your options by “lowest investment to start” to “highest investment to start.”
For example, when I was thinking of leaving my corporate job, I considered:
Becoming a novelist: lowest-investment to start, you just start writing a novel on your laptop.
Becoming a coach: next highest investment, you join a coaching certification program while working at your day job
Corporate training & development roles: next highest investment, you start prepping and interviewing for those kinds of roles
Getting a PhD: highest investment to start, lengthy application process, very expensive, and you have to finish it to get the benefits
Once you’ve ranked your options, actually start doing the lowest-investment option.
Notice that I didn’t say “try out” or “dabble in” or “do more research on” the lowest-investment option.
Actually start doing it. Give yourself a timeframe to fully commit to and DO the thing.
Because you’ll learn way more by actually doing it than by thinking about it and troubleshooting it in theory.
In my case, I started actually writing short stories. I figured out very quickly that I wasn’t good at it, and I didn’t like it.
Then I went and actually got a coaching certification. I had plenty of concerns and questions about this path! And once I got started, I figured out how to resolve them, in practice, not in theory.
This isn’t a forever commitment. Do it for a month or two or three.
But actually do it (don’t just try it), and you’ll get WAY more clarity than if you spent that time endlessly trying to decide what to do.
Stuck Point 7: You lose confidence when you get No’s.
You know what you want. You know you can do it well. You know there’s demand in the market. You’re out there actually doing it.
And then you get a No. Or 3 No’s. Or 10 No’s in a row.
And that’s when the self-doubt starts creeping in… “Am I crazy? Am I missing something? Can I NOT actually have what I want?”
Here’s the amazing thing about No’s: Your reaction to a No tells you exactly where YOU are wobbly in your own confidence.
Some No’s will roll right off your back. Those are the places where you’re already solid.
Some No’s will stick in your brain and make you rethink everything. Those are the places where you’re still wobbly.
And here’s how to use your No’s to get UNstuck rather than more stuck.
Go to the wobbly place that’s been revealed by the NO and make it stronger.
Make that thing into an asset, not a liability, in your mind.
Someone thinks you don’t have enough experience? Why are your fresh eyes and new perspective actually an asset?
Someone doesn’t understand what you pitched them? Where are YOU not clear on what you offer, and how can you get even clearer?
Someone thinks you’re asking for too much money? What’s the case for why you’re worth every penny, and more?
If you use No’s to question and doubt yourself, you’ll stay stuck. Every random opinion will blow you in a different direction, and it’ll be very hard to see something through to the end.
If you use every No to get even firmer and more confident in yourself and what you have to offer, No’s will become the foundation for future Yes’s.
You don’t need to get Yes’s to feel confident.
You need to develop the skill of turning other people’s No’s into deeper confidence and conviction within yourself.
Every person that you admire has gotten to where they are THROUGH their reaction to hundreds of No’s.
All those wobbles they had — and all the re-centering that they did, to find even deeper clarity and conviction — is exactly what built the confident, successful person you see today.
There’s no other path. Growing through the struggles is the only way.
So if you’re in the middle of the struggle…
Don’t worry. You’re on exactly the right track.
I just gave you all the answers…
So why would you still need a one-on-one coach?
Because coaching guarantees follow-through.
I talk to so many people who are reading books, listening to podcasts, going to webinars, and have no shortage of good ideas rattling around in their mind.
Ideas don’t create results.
Implementing ideas creates results.
And you cannot fail to implement when you have a coach.
Because no matter what happens, we will keep troubleshooting and adjusting and trying new things until it’s done.
You cannot backslide when you have a coach.
People often wonder whether they have the time and money to invest in coaching.
My question is: Do you have the time and money NOT to invest in coaching?
Can you afford NOT to be making consistent progress on your dreams and goals?
Where are you moving slower and less effectively, because your fears are getting in the way and you don’t have an expert partner to help you resolve them and stay on track, every single week?
Where are you losing money, because you’re staying stuck and confused longer than you have to be?
This masterclass gives you the map to your destination.
Coaching gives you a guide who walks with you every step of the way and guarantees that you cross the finish line.
You don’t have time to waste. Let’s get started today.
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