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When You Hate Your Job – But Can't Leave.

career Jan 30, 2024

There aren't many worse feelings than rolling into bed, anxious about what you have to do the next day.

Sometimes, it's one-off things like a dentist appointment. But if it's every weekday because you can't stand your job?

Spending your prime years dedicating two-thirds of your waking hours to something you don't enjoy... That is NO way to go through life. 

But you wanna know the BEST way to re-energize not only your career.. but your entire life?

Build your next career move.

Notice how I didn't say get a new job. Because let's face it – can you really be happy just jumping from one corporate job to the next?

Letting that dream pursuit inside you die – without ever giving it a real chance to come to life?

Not on my watch.

If not for the pleasure in building your own thing that's aligned with YOUR interests and values.. then for the ability to work on your own and never need approval for your vacation plans again.

Here we go..

When You Hate Your Job – But Can't Leave.

Table of Contents: 


#1. Review old jobs

I mean ALL your old jobs. Even that first one back in high school.

You see, you took a skill a job from every job you've had. In that waiter / waitress job – you learned people skills. And in your professional jobs, you've learned soft skills like communication. And hard skills, like Excel. Or project management.

Is there something buried in all these old job skills? Maybe. That's the point of this exercise.

You may find something you've overlooked that useful for you today. It's easy to think back of these and have them floating around your head. But getting them on paper (or electronically ) is helpful in taking these data past points. And spinning them into something you can use today. To create something on your own, giving you the time and location freedom you crave.

In fact, my very job – slicing cold cuts at the local deli / butcher shop – is where I found a knack that I have:

The ability to connect with people in a short, 90-second interactions.

Having a list of these skills can help you zoom in on what areas would acceptable career choices. Ones where you're positioned to thrive.


#2. Go deep on your interests

If you're anything like me, you forgot to ask yourself one simple question at 18 – when you chose your career path:

Will I even enjoy this?

We tend to lose sight of our interests once they're buried in all the things we 'should' look for in a job:

  • Salary
  • Prestige
  • Career advancement

When I was in high school and trying to decide my path, I thought about physical therapy. I always enjoyed exercise, but didn't see a way I could make a living doing it. I thought physical therapy was the way.

But all I remember hearing when I'd mention this to others:

"You'll end up taking ankles all day long."

So I nixed that idea. And chose finance. Solely because it was thought to be in demand and had high starting salaries.

I have no regrets. Because it was high-paying. And it taught me a critical lesson:

If you choose something just for money, you will tire of it. It's not a matter of IF you tire of it. But when.

There's nothing wrong with choosing a career only for the money. But you will be faced with this dilemma at some point. So be ready.

After my 11 years in finance, my love for fitness was still poking through. And I started a fitness studio as my first move out of corporate. And it indirectly led me to what I'm doing today.

So what is it you're interested in? What do you like to do in your free time? What is the thing you're going to do anyway, even you don't view it as a potential earner or career?

Part 2 of this massive data collection exercise: take note of those things you enjoy doing. How they make you feel. What you like about them.

For example, you may like to cook. But it's the serving of others or providing a wonderful experience for people that may what you love.


#3. Go to the bookstore

This step is my favorite. It's the only store I'll go to without an agenda. And won't think twice about buying anything. It's one of my happy spends.

But there are some important steps to remember here:

First, we want to see where you naturally gravitate. What do you enjoy learning about? Where do your genuine curiosities lie?

And second, we want to pretend you have 'f*ck you' money. Why?

Because we don't want to know what books you feel you should read because of the career you're in now.. and don't like. I used to try to force myself to read accounting and finance books. No genuine interest. But I felt I had to get smart if this was my career choice.

But since I've left? Never ONCE heading back to these sections. 10 years running now..

Pay attention where you head.

One of my favorite sections was always self-improvement. Much of what I've read in these books, and my personal career experience, forms the basis of what I coach others on today.

Third, run it through a quick 'filter' to make sure it has some market potential. Or not. There are tons of people earning a living doing something you'd think has zero earnings potential.

Don't limit yourself here to what you think is marketable. Let's just jot down the sections.


#4. Review your experiences

This is where it starts to get interesting.

There are things you've worked hard to accomplish that others would love to do. Everybody has something. Maybe you:

→ Run marathons
→ Overcame cancer
→ Built your own website
→ Learned a second language
→ Moved abroad and found a job.

You can take experiences just like these and begin sharing content about them. Think about the concerns, feelings, and fears of something just embarking on the same journey you did. Wouldn't it have been nice to have someone who went through the same thing – help YOU through it?

Well you can do that for someone else. Something you're experienced in. Know all the ins and outs. The emotional price. Think about what you would have paid to have that experience been made that much easier for you.

And the good news here:

You can get started right away. Brainstorm all the problems / obstacles someone has trying to accomplish your thing. And solve them all for free through social media content.

Position yourself as the authority. Build trust and likability. Offer a paid coaching / consulting call to start.

Use these calls not only to solve / guide your client in more detail. But also to learn more about their troubles. And future ways in which you can help others solve them.

You'll need little to no money to get started. And you don't need to be an expert to help someone else.

You just need to be a few steps ahead of them. Meet them where they are, and guide them to where they want to be.


#5. Call your best friend

I've known my best friend for 25 years. He knows everything about me. How my relationship is going. How my parents are enjoying retirement. My goals for the next year. About the prostate trouble I was having (TMI?)..


He also knows where I shine. And I'm sure your best friend knows too.

Something funny happens when we talk about work. If we chose a career purely for money and have grown tired of it, we'll say the title, the industry, the company. Talk about the benefits to justify why we're doing it. And then give a little shoulder nod with some nonsense closer like, "eh, pays the bills."

But when we talk about something we enjoy doing, our entire physiology changes. We stand up taller. We talk faster, as if we're so excited we can't even slow the words down enough to let them out at a reasonable pace. Our eyes get bigger. We become charismatic and authoritative.

We may not even realize it's happening. But everyone around you does. And your best friend has most likely gotten a front row seat to this many times.

So if you're struggling to figure out what topic causes YOU to show these symptoms, call your best friend and ask them this:

I'm at my absolute best when I talk about _______?

And if your best friend is a rascal like mine, you'll get some smartass answer first. Like bonging beers in the woods in high school. But they'll get to the good stuff too.

They'll tell you what area you shine in. What your strengths are. What areas you have experience and authority in. And they can easily see the changes I mentioned earlier – standing up taller, talking faster, etc. – when you start talking about your thing.

Now they may not know exactly what you should do with this topic that lights you up. And none of these exercises on its own will do that. This is a data collection exercise. And this is data.

Maybe your best friend tells you relationships are your thing. Or career advancement. Or education. But they won't likely say you should write a book on post-breakup recovery. You'll need to analyze the rest of the data from these exercises to figure that out.

On to the next step..


#6. Take a personality test

This is a wild card. And not #1 for a reason.

It's like career astrology. But with a bit more data.

But it's not completely useless. It can provide clues to which careers those with your same personality test have thrived in.

For example, if you're a 'Defender', you'll see others with the same type excel in collaborative, team-oriented workplaces. So maybe your dream gig is not in a high-pressure, competitive environment.

Or take mine – a Protagonist. They gravitate towards careers with a more altruistic purpose, like teaching or coaching. This one seems spot on.

I used 16 Personalities, but there are many others available. Any one of them can point you in the right direction and provide a glimpse into what you may good at. And enjoy.

Totally worth the 10-minute investment.

And if the career direction is a bit off, at least you'll walk away knowing which celebrities have the same personality type as you. (Mine: Barack Obama, Oprah Winfrey, Ben Affleck).


#7. Identify where others ask for your help

When I was at my corporate job, I focused heavily on my wellness outside of the office. But only ffter a few years of eating quick, crappy foods and sitting endlessly at my desk did a number on my waistline.

After I decided to do something about it (fueled by a breakup!), I dropped over 20lbs, got super lean, and was crushing adventure races a few times a year.

My friends started to notice. They wanted to know how I did it, asking me what I ate and what my workouts looked like.

I would send articles and workout routines. Supplements and nutrition plans. Until one day, I decided to compile exactly what I would do if I was in the same position as my friends that were asking.

I lost 12lbs in 30 days. I had some others try the program. The ones that stuck with it for at least 30 days all lost over 10lbs.

So I took this program, created an ebook, started an Instagram account, and started selling my book online.

This was how Simple Man Guide was born.

It's since evolved into a coaching platform to help those feeling trapped in a 9-5 role create their own 1-person business.

But it all started because I paid attention to what where others were asking me for help.

Now, what is it that your friends ask YOU for help with? Maybe it's something training related. Organizing a cluttered home. Or planning a vacation.

And as I said in the very first step: there's something in there. Now you just have to find it.


Now what...

We have all this data. Our skills. Interests. Experience. What others ask us for help for.

What do we do with all of it?

We sit it on. Think. Create endless combinations of how it could look together.

Or as one of my early inspirations in pursuing my own path, James Altucher, puts it:

Idea sex.

We toss all these things in the blender. Let them mix and marinate with each other.

An once an idea starts to come into focus:

I'd start creating content around it. Why?

Because you'll find your voice. And this can take a while so there's no point waiting until you think you have the perfect thing.

It will evolve. It may change completely. Like mine. But when you start putting things out there, you get feedback. You see what attracts people. What gets responses. What's helpful for people. And you can start to focus on these areas.

This is often a long process. And the only way to shorten it – is to get out there and start.

Waiting for perfection only keeps you frozen on the sidelines.

Some other helpful things

So it's time to take action.. and you still don't know where to start (come on, I just gave you 7 steps ha!). Here's a few other things you can do with a career transition on the horizon...

1/ Get finances in order

Building up savings cushion and taking a deep dive into your expenditures can only help extend your financial runway. And give you more comfort as you head into what can seem like a pretty scary change.

I've created an entire guide to get you started.

2/ Prime your network

Making a move like this can put us in a state of limbo. The 'safety net' our corporate job being gone can feel like being thrown in the middle of the ocean with no life raft.

So make your network your life raft.

Be sure to reach out to contacts who could be potential job opportunities for you if things don't work out with your new venture.

That's always a possibility, so it's nice to feel prepared. And it will give you the comfort of knowing you have options.

3/ Be grateful for what the job represents right now.

Right now, it's a paycheck. It covers your bills. Allows you to do things you want to do. Buy things you want to buy. You're learning skills you can take with you in your next role.

And even if you're unhappy with it now, understand that it does NOT have to represent a long-term option for you. Think of it as a stepping stone. Or a lily pad. Leading you to what you really want to do.

Remember, your career is LONG. And gone are the days of the Derek Jeters – those that stay with one team / company their entire career.

If you want to continue growing, racking up skills, and earning more – you'll need to be prepared to make moves.

And if you follow the steps in this guide, you'll be ready.

Final Thoughts

Be kind to yourself. This is not a quick process. So if you don't have it figured out after writing in your notebook over a coffee or two – don't sweat it.

One of my favorite quotes comes from a song called 'Everybody's Free' by Baz Luhrmann. It's filled with solid life advice, including this:

"Don’t feel guilty if you don’t know what you want to do with your life
the most interesting people I know didn’t know at 22
what they wanted to do with their lives,
some of the most interesting 40 year-olds I know still don’t."

Including me..


Whenever you're ready, there are three ways I can help you:

1. Free blueprint full of tactical tips to build your escape plan here. 

2. The 'DIY', build your escape plan option with over 50 interactive lessons – The Corporate Escape Academy.

3. We'll build your escape plan together through 1:1 coaching – book a call with me to apply.