Why You’re Stuck: How to Figure Out What’s Really Holding Your Career Back

Have you ever had one of those mornings when you wake up and, before you even have your coffee, you already feel tired of it?

It’s not necessarily because you hate your job. You might actually like the people you work with, care deeply about the work and for all intents and purposes, you probably have a successful career.

But, you’re starting to wonder if this is basically as good as it gets.

You’ve been in the same position for a long time, maybe several years. You have been seeing other people move into bigger roles, while you keep doing what you have always done. Nobody seems particularly interested in sponsoring you or helping you figure out what you need to do to be considered for positions with a bigger impact. You might even have applied for something and not gotten it, or worst case – you’ve reached the point where leaving this role feels a little risky, because you think you could end up somewhere worse.

After a while, you start imagining another ten or twenty years of rinse and repeat, doing the same exact thing… And the thought becomes: I’m stuck.

Once you have thought about something for long enough, there is a possibility that you stop questioning it. It stops feeling like a thought and begins to feel like a fact.

But hang on… before you keep trying to work harder and harder, holding everything together behind the scenes and assuming you already know why decision-makers are not considering you for something more strategic or challenging, let’s work together to figure out what problem you are actually trying to solve.

You may be completely right and maybe something is blocking your path.

I just don’t want you to decide what it is before you’ve really examined the situation, from all sides.

The thing is, you can work incredibly hard to solve the wrong problem, and end up exactly where you are today. You can take another course, get another qualification, work longer hours, take on more responsibility, or decide you just need to be patient for another couple of years. None of those things is automatically a bad decision. My grandma used to tell me that anything new you learn is something that “no one can take away from you,” which I agree with 100%. The thing is, if you are taking all these actions in order to evolve in a way that let’s you have the positive impact you want to have – I just want you to make sure all those things are necessary.

So, first – let’s get curious about what is actually happening in your situation.

I had a period in my career where I thought I needed to get qualifications and years of experience to apply for a couple particular positions I wanted… and as a result, I wasn’t taking any action, other than learning or going to certification classes to make my vision into my reality.

When I had my first civilian program-management job, right after I retired from the Navy, I stayed in that first job for about three years.

Some really cool opportunities came up while I was there. They were definitely a step up in responsibility and level, and I was interested in them.

I honestly thought nobody was going to let me have those positions because of my own perceived lack of experience.

The funny thing is, I had already finished a 24-year Navy career. I was already certified in program management, and I already had 6+ years of pure program-management experience in the actual Program Office these fresh opportunities were emerging.

But I had not been in this exact civilian job very long, and somehow I had decided that was the thing that mattered.

So I kept doing things I thought I needed to do to be ready.

I went to an in-resident 400-level program-management course intended for major program managers. I did other training, got other qualifications, and of course I continued leading my team.

There was nothing wrong with doing any of that.

I love learning. I still believe deeply in developing yourself and life-long learning.

But looking back, I think I was also doing those things because I was trying to make myself feel like I was ready.

At the same time, I was creating an enormous amount of evidence right in front of me that I was not really counting.

When I first took over that program, our customer was extremely dissatisfied.

There was basically a standoff between the program and the fleet. The fleet would release long, formal, official lists of everything that was wrong with the program. Then, the program would release long formal, official lists explaining everything that they had already done in the past.

I had literally just retired from the Navy when I took over the program, so when I read all of this official correspondence, I remember thinking that these two sides were talking past each other, and they were certainly not listening to each other anymore.

They were simply restating their own positions over and over.

The fleet wanted more support for maintaining the system. The program office kept explaining that it could not afford to provide everything the fleet was asking for. There was more complexity than that, of course, but that was a big part of what was happening.

We started working with the fleet on priorities. There were lower-priority items they really did not care very much about, so we unfunded those. We implemented better help-desk support and made other changes that helped the fleet feel like it was getting better support for its systems.

Over time, we started rebuilding the relationship.

Through that work, what had been a somewhat hostile customer relationship became a pretty good relationship.

And that is actually one of the hardest things to do.

Sometimes it is easier to engineer something and install a modernized system than it is to deal with a culture that has become a mess.

It was not only the relationship either. We transformed the way we did installations and the way we communicated. We improved training and help-desk support. We improved our schools, updated the training, and started providing additional ad hoc training.

A lot happened during that period. We were making all of those changes while still continuing the capability and modernization work the program was responsible for.

Looking back now, I probably had all the proof I needed right in front of me.

I just wasn’t looking at it that way. Eventually, the head of our larger program office called me into his office. There was another program that had been stuck and needed to move, and because of the success we had on my current program, he asked if I wanted a different opportunity.

They moved me to that program to help get it moving. It was basically at the same level, but it was a harder problem. I was successful there too.

Something about that experience made me realize, Oh. I’m probably underestimating myself. That was when I finally started applying for harder jobs, and from there I ended up on a trajectory that really was not very long to where I am today.

When I look back at those first three years, I think I was waiting for evidence that somebody else believed in me.

I felt like I was capable of more, but I was waiting for somebody else to confirm it.

I was lucky enough to have a supervisor who recognized what I was doing and decided to give me a shot. But, when I look back at it now, I have the rear-view understanding that no one had actually rejected me from all of those harder jobs – because I had not even tried to get them. I didn’t tell one person in my sphere of influence that I was interested.

I had decided ahead of time that I knew what the problem was.

I decided that, “I have not been in this exact job long enough.”

Meanwhile, I could have looked at the customer relationship we had changed, the problems we had solved, the systems we had improved, and the judgment I was already using. With this evidence – I could have at least conducted some simple analysis – you know, I could have taken an honest accounting, about myself and whether the evidence supported the story I was telling. That does not mean I would have gotten every job, or any job I was looking at, back then… I have no idea, but, I could have tested the question instead of answering it for everybody else.

So What Does “Stuck” Actually Mean?

If you were sitting across from me and told me you were stuck, I would not immediately tell you to network more, work harder, polish your résumé, or go find a sponsor.

I would have a lot of questions first.

I would probably begin with something very basic: What do you actually want?

You might know you want something more, but that is different from knowing what your definition of “more” means.

Maybe you want greater strategic responsibility, the ability to scale your impact, something that flows better with your overall life, different work, more money, more freedom, or the ability to influence decisions that you currently only execute.

Once you know that, ask yourself, “Who else knows?” Have you told anyone?

That sounds simple, but I think it matters a lot.

If nobody with the ability to help you knows that you want something different, you have learned something about the problem already.

Next, I want you to understand whether readiness really is part of the problem. There may genuinely be something you still need.

Being fantastic at the job you have does not automatically mean you are ready for every job above you, but before you can lean toward “yes, you are ready,” and “no you aren’t ready,” you have to analyze: What does the next kind of work actually require?

Look at the judgment, experience, scope, relationships, and responsibility involved. Then compare those requirements with what you have actually demonstrated.

You may find a real gap.

Great. Now you have something you can work on.

But you may also discover that the general feeling I’m not ready is much bigger than the evidence supports.

That leads me to another important question:

What real evidence are you using to judge yourself?

Think about the things that have changed because you were there.

What difficult problems have you handled? Where have you already made consequential decisions that directed efforts in a positive direction? What level of responsibility do people regularly trust you with? Where are you already working above and beyond your own scope and seeing larger possibilities for your organization or your industry?

Some of the evidence you notice will feel common, normal to you because you have been doing them for years. You don’t even notice them anymore.

That does not make them meaningless – if something comes exceptionally easy to you – you might not see it as anything special, at all.

This was part of my own problem. I gave enormous weight to the moment somebody senior finally said, in effect, Yes, I think you are ready for a harder problem.

I gave much less weight to the evidence I had created myself, or to my own thoughts about what I was capable of.

I am not telling you to swing all the way to the other extreme and decide that you are spectacular and everyone around you is simply too blind to appreciate your brilliance.

That is definitely NOT what I mean here, not at all.

I am asking whether you require an extraordinary amount of external validation before you’re willing to believe what your own work and successful execution to this point has shown you.

There is another possibility that became even clearer to me as I worked through Episode 1.

You may be extremely visible for your execution and still not be visible for judgment.

Everybody may know you are good.

Your boss praises you constantly. Your colleagues trust you. If something complicated goes wrong, everybody knows exactly who to call.

But what do the people influencing your future think all of that means?

Do they understand the judgment underneath the result, what your thought processes were that led you to such positive outcomes?

Do they know you were the person who noticed the root cause while everyone else was still arguing about easy to see symptoms?

Do they see how you connect information across different parts of the organization? Do they hear your reasoning about the customer, the mission, risk, resources, people, and what needs to happen next?

Or do they mostly know that if they hand you something difficult, that you will take care of it?

That distinction is worth paying attention to.

Access sometimes creates a completely different problem.

Perhaps you are ready and there is meaningful evidence of that, but nobody who can actually influence your future knows enough about you to advocate for you.

Maybe no one has invited you into the meetings where your broader judgment becomes visible. Maybe no one has assigned you a stretch assignment that would allow you to demonstrate a specific capability the organization claims you need.

If somebody keeps telling you that you need experience while never giving you any reasonable opportunity to get that experience, I would be curious about that.

Episode 1 gave us another possible explanation, which is the Dependability Trap.

If moving you creates an immediate operational problem because too much important work still depends on you personally, then that may be part of why you are not moving.

It does not mean dependability is bad.

It means we now know something important about the system around you.

And sometimes, after we look at all of this, I may agree with you:

Your organization really may be the problem. I just don’t want to start there…. Because I like to find the areas where you have more direct agency.

Examples of an organization being the problem are: There may be only a handful of senior positions and the people in them may not be going anywhere for years. Unconscious Bias, of many types, may be affecting decisions. Organizational Politics are always at play, and to what degree may make things more challenging. A particular leader may be unwilling to support your movement, or your organization may simply not offer the kind of future you want.

Those are all circumstances.

We work with circumstances here, I do not pretend they don’t exist.

But before I decide with you that your organization has closed the path, I am going to want to know what you have actually done – what receipts do you have to show to light up the barrier that you see.

If everything has happened inside your head, we do not have very much evidence yet.

You can have the most elaborate goals, plans, dreams, and explanations imaginable, but if none of them have made contact with another human being or the real world, we still have a lot to learn.

On the other hand, if you can walk me through all the meaningful things you have tried—different conversations, different opportunities, development work, stretch assignments, applications, relationships, other parts of the organization—and the same barrier keeps showing up, then that is a barrier we’ll raise in priority to find a way around.

We are not trying to prove that you OR the organization are the problem.

We are trying to figure out what is actually happening. Once we know for sure – it will be easier to address. Once we have a better idea of that, you have something you can actually make a decision about.

If there really is no room where you are, you do not necessarily have to wait fifteen years for your turn.

You might see a gap in the organization where you could propose a new position that creates value. Another part of the organization may urgently need your experience, or an entirely different organization or industry that needs the same capabilities you have spent years developing.

I do not know what the answer is for you.

I just want you to stop assuming there is only one. I believe that with your special mix of superpowers – that there are many ways for you to succeed, we only need to figure out what your options are to move down the path so you can see them too.

Here’s Your Experiment for This Week:

Start with a brain dump. Take a piece of paper, open a document, or use whatever you like, and finish this sentence as many times as you can:

I am stuck because _______.

Do not try to fix the thoughts while you are writing them.

Get all of them out. Your page could include things like: My boss will never support me. There are no opportunities here. I do not have enough experience. Nobody knows what I can really do. I waited too long. Leaving is too risky. Nobody is going to sponsor me.

Whatever is actually in your head belongs on the page.

When you are done, read through it and circle two or three statements that have some real weight for you. You may be surprised by one of them. One might make you angry. Another may create a strong physical reaction when you read it back. Choose one.

For the next five days, I want you to treat that sentence almost like a scientist would treat a hypothesis.

You are not trying to prove yourself right.

You are not trying to force yourself to be positive.

You are looking – you are curious, following the data, like a fascinated scientist.

Suppose the sentence is:

There are no opportunities here.

Okay. Pay attention for five days.

Look at the opportunities your organization is actually advertising. Listen for projects that are starting or problems leadership keeps discussing. Notice gaps that nobody seems to own. Pay attention to work the organization clearly needs even if nobody has created a formal position around it yet.

Also notice the opportunities you dismiss almost immediately.

Why did you dismiss them?

Was it because they genuinely do not fit what you want, or did you decide you were not a candidate before anybody else got a vote?

At the same time, notice evidence that supports the original thought.

If there really are no opportunities, I want you to see that too.

This is not an exercise in making yourself feel better.

Now imagine that your sentence is:

I’m not ready.

Your five-day experiment looks different.

Start defining what ready actually means for the kind of opportunity you want. Then pay attention to the evidence from your own career.

What are you already doing?

Where do you already have the capability?

Where is there a genuine gap?

You may find something you need to develop, and that is ok, that is a direction you can go.

You may also find that you have been walking past evidence about yourself because you were waiting for somebody else to tell you that you are ready for more.

If you get stuck doing this alone, talk it through with somebody you trust.

A friend, mentor, colleague, or coach can give you another set of eyes.

That is different from asking somebody else for permission.

You are not saying, Please tell me I am good enough.

You are asking another thoughtful human to help you see whether there is something you are missing.

At the end of the five days, come back to the thought you chose and ask yourself:

What do I know now that I did not know when this was only a sentence in my head?

You might discover an opportunity you genuinely want.

You may realize you are excited about possibilities you had stopped noticing.

A capability gap may become obvious, or you may recognize that you already have more evidence than you thought.

Perhaps the issue is access. Perhaps it is the Dependability Trap. Perhaps your organization really is telling you there is very little room.

Whatever comes back, now you know something you did not know before.

And you can decide what to do with it.

Then tomorrow morning, when you wake up and have that same thought again.

I’m stuck.

Your circumstances probably have not transformed overnight.

But maybe this time you can catch the thought before it becomes the entire story.

You make your coffee, as the sun is just beginning to come up, and there is that little bit of morning light on the horizon.

For a minute, you remember to get curious.

What else could be true?

What have I not considered yet?

What evidence is already right in front of me?

You do not need to answer all of those questions now.

Just go into the day on the lookout for your evidence.

As you finish that cup of coffee, you start to see it: there is hope.

What's Coming in the next episode:

One possible result of this experiment is that you will discover you do need to focus more on preparing to be ready for a new opportunity.

There is a skill or a form of judgment that you still need to develop. Or you may realize you already have more evidence of readiness than you thought.

Either way, we run into another problem very quickly:

High achievers hear things like “be more strategic, think bigger, or you need more executive presence” all the time.

I think that kind of feedback is almost useless if nobody explains what it means in the actual work.

So that is what we are going to discuss in the next episode.

We’ll look at what strategic thinking actually looks like, what another person would be able to observe you doing, and what kind of evidence begins to demonstrate that you are ready for broader responsibility.