How to Cope with Career Uncertainty, Boredom, and Professional Angst

Several years ago I reached all the goals I’d been aiming for professionally (at the time).

I’d climbed to the highest possible rank in the company for my respective skillset – a company whose mission I believed in. I had autonomy to choose which big problems to work on in the business. I was making great money. I’d gained respect and confidence and a robust skillset.

In other words, I had achieved everything I thought I’d been working to accomplish. 

Still, something felt off.

In spite of reaching what felt like the pinnacle of my career, I encountered a surprising feeling. 

It was not happiness. It was not excitement. Nor pride. Nor contentment. But boredom.

The feeling surprised me. I thought once I achieved my goals everything would sort itself out. Like the attainment of my goals warranted some kind of enlightenment.

But instead I found myself questioning everything about my station in life.

Should I leave my “dream job” to venture out on my own?

Should I find a new job?

Is it possible to reignite the fire I felt while I was working toward my goals?

Am I in the right place?

Does this make me ungrateful?

Am I missing something?

And on and on the second-guessing and uncertainty was overwhelming.

Because I needed to have certainty. I craved it. Still, I found myself staring down a path obscured by fog.

In the months and years that followed I would learn several big lessons about facing down uncertainty, boredom, ambition and professional angst.

I’ll spare you all the gory details of that journey and instead just get to the hard-earned advice.

If you’ve ever felt uncertainty about what to do next in your career, or uncertainty as a byproduct of boredom, or professional angst springing from impatience…then these tips might hit home with you.

How to Stare Down Uncertainty, Boredom, and Professional Angst

1. Don’t look to your job to satisfy every dimension of your curiosity. 

If you’re relying on your job to provide all of your personal and professional development, then you’re doing it wrong.

We’re all multi-dimensional individuals with ranges of curiosities that would be impossible to satisfy through a single job. Find a way to prioritize your own interests beyond your day-job. Lean into those interests. Cultivate your creatives capacities outside the office.

Reserve a part of you just for yourself and your own passions. This will recharge you; offer you a cathartic outlet; and make you an overall more interesting, well-rounded person.

2. Aim for clarity, then challenge.

Before you know what you want to do, it’s okay to go into information-gathering mode. I called this  “Your Quest for Clarity.”

Try stuff. Eliminate options that don’t seem interesting. Then double-down on the skills / career path / interests that really light your fire. Mainly, don’t do stuff you hate.

If you iterate enough, worst case you’ll find something tolerable and best case you’ll find something that excites the hell out of you – anywhere in between those two poles is still a win. But a word of caution – not long after you “find your thing” you’ll eventually get good enough that the job becomes easy. This is a danger zone.

Continue to seek out challenges that will force you to grow and develop (even if they are outside your job). When things get too easy, it’s an early warning sign of impending stagnation. 

3. Don’t burn down everything you’ve built on an impulse.

It can feel exciting to think about exiting a situation in the name of adventure. You could leave it all behind today to go chasing some other big hairy audacious goal. Maybe you’ll start your own thing. Or land an awesome new job at another cool company, and then everything will be great!

Sadly, the new adventure will probably lead you to the same spot you’re in eventually. Because the truth is, sometimes you will feel bored in your career. We live in a world of in-your-face instant gratification. There’s always a new shiny object that seems like a better path.

Patience and focus can be superpowers in your life and career. If you can find a way to trudge through the boredom, and still do your best work in the meantime, you’ll unlock the true power of uninterrupted compound interest in your career. Which means more options, not fewer. Don’t leave a job you don’t hate just because you think there may be some hypothetical better option out there. The situation you’re in may offer you more upside than you realize. 

4. Give yourself permission to daydream about your options

When you find yourself unsure about what to do next, or bored in your current situation, allow your imagination to go to work. Keep a journal of ideas. Daydream. Allow your creative capacities to run wild.

It’s okay to explore those options mentally. It can offer a release. But the brainstorming time can also lead to actual tangible developments – which can take time, energy, and focus. It’s rarely immediately obvious what steps you should take next. Give yourself some room to visualize the multiple future possibilities.

5. Target universally good actions.

While you’re in the “ugly in-between” of boredom or uncertainty, there are still positive steps you can take to build momentum.

First, you can take universally-good actions. Like saving money, paying off or paying down debt. Expanding your network. Building an audience. Creating content around your areas of interest. Writing regularly and publishing your work. Etc. The list goes on and on.

But these kinds of positive actions will expand your option set as you gain clarity; and ultimately make it easier for you to say yes once you figure out your next step. 


These are just a few suggestions from my own lived experience dealing with uncertainty, professional angst, and boredom.

You owe it to yourself to take your personal and professional development into your own hands. Don’t settle for a life that bores you. Channel your energy into your own interests and creative capacities.

Keep iterating and working hard. Even when you may not know where it’s leading.

Eventually, those positive behaviors will lead you to a place of more clarity than you have today.

Goals as Sustenance

I remember this group of girls at my high school who seemed to want nothing more from life than to date a good-looking guy and win homecoming queen.

At least one of them got everything she ever wanted (only one person can win homecoming queen per year, yanno?).

But it never made much sense to me to shoot so low.

If goals are already within your reach, then what’s the point? Where is the meaning to be found from life?

Goals as a forcing function

Instead, I think it’s more useful to choose goals that force you to change.

Goals, by very definition, are about manifesting a different future state. But there’s a big difference between bringing about a future state that’s already a forgone conclusion and in manifesting something you’re not yet capable of creating.

Only chasing forgone conclusions snubs your own potential – your potential to become something more than you already are.

And goals that require you to cultivate that potential – to become who you are not yet but could be – those are the best kinds of goals.

Because it is the process of metamorphosis that enables us to reach new heights.

And we’re all equally free to pursue and prioritize the cultivation of our highest potentials. Even if it’s an unequal distribution in people who actually do that.

In other words, we all have the opportunity to manifest a better future than our present circumstances. If we really desire it, we have the option to escape the life we were born into, and to turn the hand we were dealt into a winning one.

The Cycle of Goals

The process of setting and working toward a goal has restorative and regenerative properties.

It’s half therapy and half fertilization.

The therapy part requires us to examine who we are – who we were in the past – and contrast that against an ideal future state.

The fertilization aspect takes the seed of an idea (our idyllic future) and grants it what it needs to grow – motivation, inspiration, resolve, a plan of action, etc.

In that sense, the undertaking of choosing a goal then moving toward it is a form of self-transformation.

It is the process of continuous evolution. Of correcting errors in your past by improving your behavior in the present, in pursuit of an further improvement still in the future.

And without a continuously ascending target above the horizon to aim at, then we’ll probably get everything we ever wanted.

Which means we probably aimed lower than our potential could have allowed. And I can hardly imagine a fate worse than that.

What would the best version of yourself be like?

Here is a useful tip I’ve discovered whenever I encounter unknown situations:

Just ask yourself, “What would the best version of myself be like in this moment?”

(This is particularly useful for robots, like that Facebook founder, who are only pretending to be humans. Just a joke. Chill out. Don’t put me on some list.)

Anyway, it’s a useful tip because it’s an open-ended question. Which forces you to flip on the ol’ imagination. Rather than asking yourself silly, self-doubting (or self-loathing) closed- ended questions. Like, “Should I do X?”, “Should I have said Y?”

This question is not meant to encourage you to shut off in the middle of real-life scenarios, so you can brainstorm how to behave. Don’t do that, psycho. Just be authentic.

It’s really meant more for reflection. Especially if you ever find yourself putting your foot in your own mouth. Or wishing you’d have handled a situation differently.

You’re going to botch it all up quite a few times in your life. Shrug it off. Then reflect.

How could that have gone differently?

“How would the best version of myself handled that moment?”

Asking these kinds of questions creates the semblance of an ideal for you to strive for in future scenarios. That, paired with the critical self-knowledge of your own past uncomfortable failures, gives you some good guardrails for future interactions.

“What’s the worst than could happen?” and “How would the best version of myself handle this?”

Aim to end up somewhere in the middle of those. Reflect. Move on with your life. Improve in the future.

Good Destination, Bad Directions

I turn 30 today (happy birthday to me, right?). Aging tends to force reflection. It gives cause to think back on decisions – the good, the bad, and the ugly. If we’re smart, that reflection offers lessons to help us improve ourselves over time.

Here’s one big lesson I’ve been meditating on:

Having the proper destination in mind does not validate your route to it.

Life is a series of goals. We make subsequent decisions in relation to our goals. Often we do the best that we can with the information we have.

But we don’t always have the best information. Nor do we always have the best of intentions. (Thought even when we do have good intentions, sometimes we’re bad at selecting the proper means.)

Still, with our limited knowledge, we aim at the highest, best goals we can fathom (if we are wise), and we dedicate ourselves to manifesting those into reality.

Except we’re not always great at bringing our ideas to life. Not to the level of perfection we all likely aspire to.

We choose our goals. Then we choose the route that we believe is most likely to get us there. Hopefully, most efficiently.

Sometimes, though, we choose the right goal but the wrong route. Which makes it incredibly difficult to see our own errors.

It can often feel like “selecting your goal” is the most difficult part of personal development. But that’s rarely true. Choosing a target is easier than hitting it.

But when you take special care in selecting which targets to aim at with your scarce resources, and you finally determine one that’s worthwhile – it can give you a sense of absolution about the means you select for getting there.

Choosing a good destination does not let you off the hook for using bad directions, though.

Even honorable goals are overshadowed by unworthy means.

The work isn’t done once you choose your target. You must also take special care as you work toward it, to ensure that you’re not allowing a desirable “end” is to justify bad means.

Radical Generosity is Good for the Soul

If you’re looking for a quick remedy to improve your life, look no further than generosity.

Generosity changes your orientation.

It opens up your purview to think instead about how to be useful, valuable, or of service to other people.

(Which is not necessarily the opposite of selfishness, properly defined. Nor am I advocating for selfless altruism. But that’s for another blog post.)

Being radically generous is a great way to restore yourself. To freely give of the best that is within you to the loved ones in your life – and even pure strangers – without any expectation of repayment.

But it’s not a one-sided transaction. Because in order to give, someone must also receive.

Be radically generous with the people in your life, with your resources, with your gifts and talents, and your time. If for no other reason than to improve your own happiness and quality of life (and the others around you, too).

Age and Perspective

The older I get the more sentimental I become. Especially about the time I get with family.

You never really know how much time you have left. I don’t say that to be morbid. But to remind myself of the importance of prioritizing what matters.

There’s a really jarring post about this from a blog I enjoy, The Tail End from Wait But Why. Illustrating your life in dots based on the average human lifespan, it forecasts “how many times left” the average person might have based on where they are in their journey.

I think a lot of us grow up fearing our own mortality, and so naturally, we avoid thinking about it at all costs. But I’m not afraid to die. What scares me much more is getting to the end and realizing I took things for granted.

This is, in part, I think, why I get more sentimental with time. The people and things in our life that make us who we are – they matter. They’re worthy of our affection, admiration, and gratitude.

It doesn’t all have to be captured and shared on social media, either. We can savor experiences without sharing them with the world.

It makes those moments more intimate. If for no other reason than scarcity. When there are no pictures or videos or archives to reflect on later, only the catalogue of our own memories.

We never know when we’re going to do our last something. So it warrants being present. We’ve got to show up for our own lives.

I don’t know when will be the last time I’ll read Salinger’s Catcher in the Rye. Or when I’ll uncork my last bottle of wine shared with family and friends. Just like I don’t know the last time I’ll take a walk holding hands with my wife.

But I want to be there for every one of the times I do get. I want to savor all of those precious moments, big and small alike – and as Thoreau once said, “to suck out all the marrow of life.”

How To Change Your World

When you recognize your own power to influence your immediate surroundings, you can make a big difference in your world fast.

You can rearrange rooms to make them more beautiful.

You can speak more respectfully to others.

You can laugh more, and invite others to join in.

You can leave things — and people — better than you found them.

You can get your life in order — personally, professional, financially.

Of course, you can do the opposite of all those things, too.

The same power that creates can destroy.

But, given the choice, what would you choose?

Will you make the world uglier?

Or will you make it more beautiful?

Today, and every day, I choose to make the world a more beautiful place.

How To Reduce the Chaos of Endless Choice Realities

One big challenge of life is figuring out what targets to aim at. We live in a time and world with nearly unlimited choices as it relates to careers, location, income goals, industry, and beyond.

So how do you navigate this – to ultimately discover the “right” target to take aim at?

Here’s one suggestion to get started: Find one goal you could aim everything you’ve got at.

By picking a goal that requires you to aim above the horizon, you force yourself to imagine who you must become in order to achieve that goal. 

This is a useful strategy for several reasons.

1. It allows you to orient yourself. Where (and who) are you today, versus where you’d like to be as a result of achieving your goal (and rather, who you’d like to be).

2. It reveals disparity. Moving toward your goals necessitates progress and change. You cannot become who you must be by accepting your current circumstances. Goal-setting contrasts the future you desire against the reality of your present, which enhances your own self-awareness.

3. It gives you a roadmap for how to behave. When you set a goal, you choose a target to take aim at. Which gives you a focal point into the future that you can work backwards from. Some choices will help you make progress toward that focal point, while others will lead you astray. 

Negotiating With Your Future

Setting goals forces us to detach ourselves from our past and present circumstances. Even without taking action on them, it offers an exercise in future-orientation.

If you really want to make headway toward your goals, then you’ve got to take inventory of your life –from the choices you make to the activities you spend your time on to your current available resources.

Taking inventory reveals positive and negative stock.

If you discover things that are holding you back, then if you really want to achieve your goals, you’ll be forced to address the baggage in your life.

Sometimes, you’ve got to sacrifice those demons at the altar of your future in order to stand a shot at advancing ahead.

Changing Course

As you go throughout life’s adventure, you’ll likely discover other targets worth aiming at – goals that you’d rather pursue. And you’ll almost always have different interests pulling you in different directions.

If you can go all-in on at least one thing – even if only for a short period in your life – you’ll build discipline, you’ll gain credibility, and maybe most importantly, you’ll build momentum.

You won’t always achieve the goals you set out to. Often, your pursuit of one goal will reveal an entirely different, more exciting path – when that happens, change course. 

This variety of life, though, should not be a cause for anxiety. Instead, it’s a good cause for excitement and enthusiasm about the endless possibilities that are waiting for you.

But you’ve got to start first. 

There are opportunities out there that you don’t know about yet. And you likely won’t discover them until you take aim at something and start moving toward it.

That’s the great adventure of life. It’s an ongoing discovery process, and you can always change course as new opportunities reveal themselves.

Failure is Part of It

There’s a scripture I’ve been meditating on for the past year or so.

It’s found in Acts 16:16-34 – when Paul and Silas are jailed in Philipi, for causing a riot. And by riot, I mean, for preaching the gospel and casting a demon out of a servant girl.

My biggest challenge with that scripture rests in their behavior after being accused and subsequently jailed – for no wrongdoing.

These guys sing while they’re shackled.

It’s as if they were so convinced of their bigger mission that the circumstances of the world could not stop them.

What happens next remains nothing short of incredible, too. When the earthquake batters the prison and breaks their chains, they don’t run. The jailer fears for his life. But Paul stops him.

He saves the jailer’s life. Then proceeds to share the gospel with him. The jailer invites them to his home, and they share the gospel with his family. Then he baptizes them all.

What an incredible story, right?

Man Makes Plans and God Laughs

This story makes me uncomfortable about my own response to circumstances that are not part of my plans.

When things don’t go according to plan, that’s failure, right? But perhaps not for certain.

I think back to some of my big failures. They were earth-shattering.

Granted, some of those came when I was not living out my potential. Which presents another big challenge.

When we face personal failure and inevitably start pointing fingers, all too often, we’re the main person worth of blame. At least, that’s been my experience.

But what about deviations from the plan when we are living out our potential? (Or at least making our best attempt to do so, given what limited knowledge we have.)

Meditating on Worst Case Scenarios

From time to time, I enjoy contemplating worst case scenario outcomes. It challenges me to evaluate my own intestinal fortitude, if you will. But facing the worst also brings me peace.

“Could I survive that?”

“How would I react?”

“Am I strong enough to endure that?”

…I wonder.

I like this exercise, though, because it allows me to explore just how uncomfortable a situation might be in advance – then contemplate what steps I could take to prevent sure disaster.

Separately, facing the worst case scenario and mentally enduring the struggle, enables me to make peace with my fate – recognizing every outcome less bad than that as a victory, in a sense.

Inevitable Failure

A final word on this topic, failure.

It is inevitable.

We all fail. But the good news is, we get to choose our battles.

It’s comforting to pretend that we can avoid failure altogether, if only we just play it safe enough. But that’s wrong. Dead wrong.

We will fail. Even if only in our own eyes – by failing to try.

What’s much more useful than attempting to avoid failure, then, is dedicating ourselves to fighting the battles that matter most to us.

That way when we fail, at least we can do so with the dignity of self-respect.

Be Attentive to the Opponents You Set Out to Defeat

I dreamed a strange dream last night. What’s even stranger, perhaps, is that I woke up in the middle of the night and the first thing that came to mind was a possible interpretation.

In attempt to extract the meaning, I’ll share it here.

I was sitting in a lawn chair in a backyard surrounded by family and friends at a celebration of sorts. In one hand I held a glass of wine and in the other a garden hoe – prepared to ward off snakes that had been spotted.

The first snakes I encountered were small. Easy to exterminate with one hand and a swift swing of the rake. But with each snake I addressed, the subsequent snakes grew larger and faster. Eventually, a rather large and swift snake appeared. As I swung at it one-handed, it lunged at me forcing retreat. I realized I stood no chance against my foe while defending myself one-handed.

There are a couple layers of meaning I’d like to address.

First, let’s talk about snakes – the opponents of your friends and family, threats to your way of life, enemies which would devour you, challenges which may poison us if left unaddressed.

I’m choosing the word opponent here, because it’s the word that woke me up last night. I don’t mean competitor as people we’re attempting to beat at some contest. The word opponent stood out to me vividly in my half-sleep state as ‘the problems which we choose to wage war against.’

Those challenges could be anything – from small personal development challenges to large cultural issues. Anything from attempting to get better with money or relationships to attempting to resist totalitarianism.

Threats that start small may grow in size if not entirely eliminated, or left unaddressed. This is my takeaway about the increasing size and speed of snakes.

If you don’t address issues, they grow into more formidable opponents.

Ok, so here’s the big one – the issue of fighting one-handed.

I’ve been thinking a lot about symbology lately. Earlier this year, I finished Jordan Peterson’s 12 Rules of Living and Beyond Order. Now I’m reading Maps of Meaning. So I’ve spent a fair amount of time recently thinking about the “snakes” (primordial threats) that lurk around the corners, and extracting meaning from our every day stories. Not to mention thinking generally about “rules for living”.

The issue of fighting one-handed is something I’ve been dwelling on lately. Not in those specific terms. But it’s come up in attempts to improve my own life, and in conversations with others who are trying to make progress along a certain dimension.

A common theme I’ve encountered is how ineffective “we” (humans, generally speaking), tend to be at making progress in our own lives when we don’t take the problems we’re attempting to solve seriously enough.

Your opponent becomes more dangerous when you don’t respect it.

Take any big or small issue in your life. When you shirk things off altogether, or only make half-assed attempts to set the world in order, resolution evades you.

The only effective way to meet your opponents on the battle field is with your full attention and full proclivities in tact.

If you want to protect your garden, don’t fight snakes one-handed.