4 Questions To Ask Yourself When You’re Stuck In Your Career

Sep 07, 2018 1 Min Read


It’s not a comfortable place to be. You felt you were on the right career trajectory but, for whatever reason, you zigged when you should’ve zagged. The change of direction caught up with you, and now, you’re just stuck.


The good news is when you’re in a state of chaos (which I define as an unpredicted or unwanted change that impacts our physical, mental, emotional or spiritual well-being) the only next step is to move toward clarity.

You can’t devolve into a more chaotic state, for example, as that would be the same as receiving an F minus on a report card as opposed to ‘just’ an F.

So, how do you navigate out of this unwanted and unpredictable state of change known as chaos and move toward greater clarity?

There’s one tool you can use. One technique, one method, one strategy, and one ‘secret’ to getting unstuck.

Curiosity is what cycles you away from chaos toward clarity. Of course, the quality of answers you find solely depends on the quality of questions you pose – that’s why curiosity is a superpower.

The moment you pose a question is the moment you infuse possibility into the moment. Curiosity presumes possibility.

The only question that ran through Roger Bannister’s mind before he broke the four-minute mile was, ‘How might I run faster?’

The only question that ran through Polaroid founder Edwin Land’s mind right after his daughter asked, ‘Why do we have to wait for the picture [to be developed]?’ was, ‘Why do we?’

Curiosity drives behaviour, which drives results.

Consider nomadic societies, for instance. Back in ‘nomad times’ the question of the day – every day – was ‘where do we go to find water?’

By asking themselves the same question day after day, nomads kept wandering, kept searching, and kept being…nomadic.

Then one day, somebody piped up. Somebody got tired of searching.

Somebody got tired of asking the same tireless question of, ‘where do we go to find water?’ and instead asked a different question: ‘Why do we have to go anywhere? How can we make water come to us?’

What happened? Results happened. Agriculture. Irrigation. Wells. The dawn of an established society that no longer felt compelled to roam; no longer had to search.

Results were due to simply asking a question that had never been asked before. The question changed, and as a by-product, behaviour changed.

One of my favourite things to do as a leadership team coach is to gather the head of each business function into a room – the head of sales, head of marketing, head of whatever – and ask them all the same question: ‘How is success defined here at Company XYZ?’

Sales define success according to units sold.

Marketing defines success based on enrolment. HR defines success according to engagement or turnover or employee retention.

The point is, the question is the same, but the end states are different, which means that the behaviours to achieve those results are different, as well. That’s why ‘organisational chaos’ exists.

Or, better yet, ask leaders at different echelons in your company what their mission focus is. Is it to satisfy customers, employees or shareholders.

You’ll get 10 different answers from 10 people – which actually begs a follow-on question: ‘How does any work actually get done around here?’ If you want a better answer, ask a better question.

On the heels of leveraging curiosity as a superpower toward ‘unstuck-ness,’ here are four clarifying questions to pose to yourself (or somebody else) when you’re feeling stuck:

  1. What’s your plan to become extraordinarily good at what you do? 

There are three types of people in this world: sheep, wolves, and sheepdogs. The sheep follow the status quo.

They don’t want to rock the boat because everybody else is moving together in the same direction and they (sheep) don’t want to be any different. They’re ordinary.

Wolves want to eat the sheep. They’ll go out of their way to entice any little sheep to part from the herd so they can gobble them up.

Wolves will go the extra mile to catch their prize but they’re motivated by ill-intention.

There’s no virtue in the wolf. They’re extraordinarily bad creatures who prey on the innocent for their own gain.

Then there’s the sheepdog. Sheepdogs go out of their way to protect the sheep from the wolf.

They put in the extra effort to wake up early and remain vigilant because they know that the wolf is coming, and they know that the only thing standing between their ‘ordinary’ friends in the herd and the wolf, is them.

That’s why the sheepdog is extraordinarily good.

Once you identify what you want to be extraordinarily good at, ask yourself two questions:

  • Why is this important to me?
  • How much suffering am I willing to endure to get there?

READ: 14 Coaching Principles All Managers Should Practise


  1. Where do you prefer to spend your time? 

Whether your answer is at work, with family or friends, don’t stop there.

Drill deeper into what you’re actually doing in those instances that give you energy when you’re at work, when you’re with your family, and when you’re with your friends.

Are you teaching? Are you speaking? Are you sharing advice? Are you problem-solving? Are you executing against a deadline?

What and who are important to you? Are your values in line with your actions?

Meaning, that if there’s a fundamental disconnect between what you do and what’s important to you, then your runway for ‘take-off’ (i.e. wherever you want to ultimately be) will be cut short and you’ll never arrive.

Once you gain clarity from this question, write out your options. All of them. It doesn’t matter how outlandish they feel. Just list them out – aim for 25 or 30.

Then, take a step back, admire your brain vomit, and look for trends and common themes. Use these as fuel for your purpose and your passion.

  1. What’s the story you want to write? 

Everybody has a story they tell themselves.

Some people tell themselves they’re no good, others tell themselves they need to be better, others say they’re not smart enough, not strong enough, or lack the social skills.

These are all stories – lies we tell ourselves to avoid doing the work because it’s easier to attribute success to an internal trait or an external ‘stroke of luck’ than it is to consider hard work as a viable option.

Most people tell themselves the story they want to hear.

Tell yourself a story that you’ll be proud to have written, and then write your own story.

  1. Will your current trajectory get you to where you want to be? 

This is an easy question to answer and understand intellectually, but the real value lies in whether or not your answer resonates emotionally.

Emotion is at the root of behaviour change. If you want to change behaviour, identify the emotion that is pulling or pushing you to act.

Here’s the difference between behaviour that pulls and behaviour that pushes:

Let’s say you want to purchase a new car. You’re ambushed by a car salesman who simply does not let up.

He uses ‘caveman tactics’ to try to beat you into submission of saying ‘Enough! I’ll buy the car already!’ That’s pushing.

Pulling is the opposite. When you’re pulled into a behaviour it’s because you feel you have the freedom to choose. You have autonomy.

This is the other car salesman who says, ‘I’m changing jobs Friday which means I don’t really care how many more cars I sell.

If you like the car at this price, let me know. Otherwise, best of luck to you.’

The first car salesman beat you into submission, the second one left with a choice.

Push vs pull.

The goal here is to identify that which would pull you away from your current trajectory and instead put you on the path you want.

Alternative question: What has ‘playing it safe’ done for you so far?

Don’t let inaction be your favourite action.

People stay on the same trajectory because they repeat the same behaviour over and over again and don’t take any action to address it. Identify what you’re willing to tackle head on and start moving.


Jeff is a former Navy SEAL who helps business teams find clarity in chaos. He is a contributor at Forbes and Entrepreneur.com, speaks at the Harry Walker Agency, and is the author of Navigating Chaos: How To Find Certainty In Uncertain Situations. What did you think of this article? Let us know at editor@leaderonomics.com

Reposted with permission.

Prefer an e-mag reading experience? No problem! This article is also available in our 8th September 2018 digital issue, which you can access here.

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This article is published by the editors of Leaderonomics.com with the consent of the guest author. 

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