7 Steps to Ditching That Dead-End Job (and Finding A Career You Love)

7 Steps to Ditching That Dead-End Job (and Finding A Career You Love)

dead end job, JOHN TIMMERMAN

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Do you have a job or a career?

Next question, do you know the difference?

We are no employment experts here at Successful and Fit – I mean we run around wearing tutu’s when we lose office bets and have weekly idea-hacks that flip business-as-usual on it’s head. These are hardly the antics of a typical employee. But we do have a pretty bad ass culture that keeps everybody pumped to come to work, most days (not including the Mondays after bachelor party weekends).

Our business runs on entrepreneurial spirit and self-accountability. But most importantly, our culture allows for failure. This is a fundamental part of our business growth and allows our staff the freedom to take risks without feeling like they are going to get the axe at the end of the day.

In order to keep pushing ourselves to be better, we need to have the freedom to fail.

Having the freedom to fail teaches us the most valuable lessons in life.

Why riding a bike to your friends house through the woods in the middle of the night is a bad idea. What kinds of things you should never ask a girl on the first date. Why you shouldn’t put that much weight on the squat bar (although sometimes we never learn).

Learning from our mistakes is a fundamental part of our growth both personally and professionally. Personally it teaches us how to be better friends, better husbands, better lovers, better neighbors and better fathers. Professionally it teaches us how to be better co-workers, better team players and better leaders.

The average American works a little over 2,000 hours out of the 8,765 in a year. That is a quarter of our lives that we are spending at our desk, or on a jobsite, or in the airport.

Us ‘Muricans work a quarter of our lives!

If we are working so much, why not make sure that it’s doing something that we love so much that it’s no longer work? I mean if there truly is a ‘meaning of life’, it probably has something to do with finding what you love to do, and spend your life doing it.

Whether its a career in nursing, or quitting your job to launch your own internet business, life is too short to waste it working somewhere, on something that makes your life depressing.

From Job to Career

It’s bad enough that we have to work for a living, but why do we often work doing shit that we hate?

Money, duh.

Being stuck at a dead end job that you cannot stand is no way to spend the one life that you have. But before you have a pity party for you and yourself, realize that there is an entire world of opportunity out there for you.

First off let’s make sure this is burned into your brain – the difference between job and career.

  • job: a paid position of regular employment.
  • career: an occupation undertaken for a significant period of a person’s life and with opportunities for progress.

By definition, having a job seems pretty lame – but “life with opportunity for progress” sounds pretty awesome right?

Most of us who are unhappy with our jobs are stuck in one of two scenarios:

A. You have a job that gets your life from golf clubs to the bar; but you are unfulfilled with it. You flat out can’t stand it, and you wish you could have a job that makes you happy.


B. You have a job that gets your life from the gym to gas in your car; but you dream everyday about starting your own business and working for yourself doing what you love.

Does this sound about right?

If not, then you are probably happy with your job, and we’re proud of you – but for the rest of us let’s make some moves and drive toward a happier life.

 Step #1: Figure out your priorities

The first thing you need to do is figure out what your priorities in life are. Is it raising a family? Is it becoming rich? Is it owning the NY Jets (Gary Vaynerchuk has his priorities straight)?

This might not be as easy as you think because your brain might be crowded with today’s priorities – and these might be different than your long term priorities.

Your number one priority this weekend might be to meet the girl of your dreams; but your long term priority is to support a happy family. Having a job in the big city might allow you to meet more girls, but working your way up the corporate ladder often leads to increased responsibility and not a ton of family time.

The difference in these priorities makes it a little tricky to ensure that you are headed down the right road. So make sure that you are thinking long term when planning, then looking at the short term milestones that will ultimately lead you there.

For example, my priorities are to have a career that allows me the freedom to travel the world while simultaneously raising a healthy family that can travel with me, without worrying about finances or obligations other than family.

In order to get there I have begun building digital businesses that allow me the freedom to make my own hours and dollars. As for the family part, well you can’t really force something like that, but working on my own terms leaves the door wide open for opportunity.

Ok your turn.

Step #2: Calculate how much your priorities cost

The next step is an eye-opening one.

Now that you know what your priorities are it’s time to calculate how much they cost. While this might also be a little tricky to do, you can get a general idea by doing some research on a little thing called the Internet.

Let’s say that your priorities are to live on a boat with your wife in Florida, while fishing and golfing everyday by the time you are 45.

To get started we will do a little research:

How much is a house boat? About $50,000 ($375/mo)

How much is the annual fee at a marina in Tampa, FL? About $1,000/mo

How much is boat insurance? About $1000/ year ($83/mo)

How much does boat maintenance cost? About 10% of boat cost = $5,000/yr ($417/mo)

How much is fishing equipment for a year? License = $17, Equipment = About $500/yr

How much is a golf course membership in Tampa, FL? $3,000-$4,000/yr

How much are your expenses (health insurance, retirement account, car payment, etc.)? Only you know this one.

Ok so now you have your yearly and monthly expenses written down, you can calculate how much money you need to make every month to live your dream.

This is known as Dreamlining, conceptualized by Tim Ferris in the NY Times Best Seller The 4-Hour Workweek. It involves figuring out how much money you need to live your dream lifestyle, then molding your actions and to-do’s around building that life.

 Step #3: Write down what you could do everyday for the rest of your life

Next lets figure out what your passion is, and how you can make it a career.

It’s simple really – think of what you could do everyday for the rest of your life and be absolutely happy?

You might be thinking ‘how can I turn my passion for Extreme Ironing into a career (yes it’s a real thing)?

Well, you could potentially take the route of starting a blog and writing about your ‘sport’ and talking to the people that share your passion – but you might have to move to Europe. You could find a job at a dry cleaning shop and hope that you work your way up the ironing board (see what i did there).

But let’s be realistic here, you have to make sure that there is an audience large enough to pay for your knowledge in order to run a profitable blog. If you are looking to work for a company, there has to actually be a company that sells shit in that industry (we didn’t come across any Extreme Ironing brands).

If you want to work to live instead of live to work, find a problem that you are good at solving, and do it for people all over the world.

This is the easiest way to find out how you can merge what you love to do with what you can make a living doing.

Here are a few examples to show you that it’s possible:

Travel and Fitness: Travel and Fitness Blog

Ice Cream: Ice Cream Taster

Horseback Riding: Horse Exerciser

Entrepreneurship: Entrepreneur Podcast

So go ahead, find your passion, then Google search until you find out how you can turn it into a career.

 Step #4: Ask yourself: Am I a risk taker?

Could you lose it all and still love life? If so you are probably the perfect candidate to become an entrepreneur.

Starting a business is a big risk, especially if you have anyone depending on you. It takes a ton of guts, drive, and the ability to learn from your mistakes and charge forward. If this sounds like you, you should look into starting your own business.

I started my digital marketing business, Good Monster,  while working for a fitness facility as a part time gig with my now business partner, Jason. We worked long hours between our full time jobs and our part time business. We began making a little extra money on the side and started to consider our business as a full time thing.

A few months later we pulled the trigger and started a full time business. My business partner has 3 kids and a wife. It was the best decision we made.

If you are not a risk-taker, then I suggest that you find someone who has a career that you would be passionate about, and simply ask how they got there. If you can keep this person as a mentor, you will have the support and guidance you need to get to where he is.

 Step #5: Interview as many people as possible

Whether you are a risk-taker or not, interviewing people who have a career doing what you want to do is the best advice I can give. That’s how we continue to grow our business – learning and asking followed by teaching.

If you think about it, why would you want to fumble through something as important as your career, when you can skip some of the pitfalls and shoot straight to the necessary steps?

Don’t be afraid to reach for the stars, literally. If your dream is to become a movie star, send a tweet to Ryan Gosling (or his publicist) and simply ask him for advice. If he doesn’t respond, just be persistent and it will eventually pay off.

Don’t be too timid with this one, go get it – after all this is the rest of your life we are talking about.

 Step #6: Write down your to-do list

Successful people don’t get to be successful without a to-do list.

Time management is the building blocks to success. So now that you have decided what your priorities are and how much they cost, found your passion and how to make it a career, and interviewed someone who is where you want to be – it’s time to write down and schedule the steps to get there.

I write a to-do list almost everyday, but I also have large, long-term to-do lists that keep me on track.

In fact our business uses one giant to-do list in order to manage our client work and our individual priorities. This is a staple in our business and we couldn’t survive without it.

 Step #7: Do it

Congratulations! You have just built the roadmap to dig yourself out of your dead-end job and begin paving your path to a fulfilling career!

All you have to do now is put this plan into action.

Be real with yourself as to what risks you can take and who they might affect. Do you research, talk with family, friends and mentors. Planning and taking that first step is the most difficult part, but staying on track and motivated is the hardest physically and emotionally.


Written by
John Timmerman
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