The Post-Grad Survival Guide


Stop Reading Quit-Your-Job Advice Articles

Ask yourself these important questions instead

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Photo: Annie Spratt/Unsplash

Quitting your job has become over-hyped and glorified. I’ve seen too many advice articles written by 20-somethings claiming to quit their jobs to pursue freedom or whatever.

More freedom! More money! Less stress! They all say.

I quit my job in 2017. I thought I was super cool. And then the panic set in. Over the next three years of working for myself and subsequently reading more quit-your-job advice articles, I’ve realized something:

Making a career on your own is difficult, risky, and agonizing. For some, it works out, for others it doesn’t.

The life experiences of a 22-year-old single dude quitting his job at Target and writing advice columns about becoming a solopreneur do not translate for the 34-year-old mother of four with a mortgage, car payment, and health insurance to worry about.

There is a huge disconnect here.

The quit-your-job advice of today has a branding problem because it’s not geared towards the average adult with financial anxiety and life responsibilities.

Which brings me to the purpose of this article. If you’re looking for a fresh, realistic take on how to quit your job, look no further.

The 5 essential questions to ask yourself before quitting your job

If you’ve recently read a quit-your-job article, take a beat. Those promises of freedom, money, and bliss swimming in your head need a reality check.

You should be asking yourself the following questions before making any life-changing decisions.

Question 1: Do I have an already established and varied means of income outside of my 9-to-5?

Here’s a simple litmus test: are you actually making money outside your job?

If you are making money, is it coming from a variety of sources? Do you have multiple clients?

When you leave your job you need to replace your income, obviously. Relying on one source of income is generally a bad idea because unlike a traditional job, they can cut you off at any point.

If you failed the litmus test above, it’s time to start building your 5-to-9. What’s a 5-to-9? It’s entrepreneurship in a box. It’s the time spent outside of your 9-to-5, those 12–20 hours of extra time a week to devote to your small ventures.

Spend the next 2 to 3 years building and testing various streams of income. Then come back to this question and see if you pass the litmus test.

Question 2: Do I have a substantial amount of money saved up for “down” months?

Some gurus say you should have at least 3 months of living expenses saved up before quitting your job. That’s not nearly enough.

I recommend at least 12, 18 if you really want to be safe. Why such a high amount? Because the first year after quitting your job is an adjustment period. Your focus should only be on building better products or services, not chasing after the next buck.

When I left my job in 2017, I burnt through the meager savings my wife and I had “saved” up. I was so desperate for clients that I took on some really bad clients (one told me to “put the baby down and get your head in the game.”) I slashed my hourly rate to attract new clients and ended up working at a fraction of the value I thought I was worth.

It’s a miserable cycle. Instead, here’s what you do.

  • Sign up for a budgeting app (like this one) and find out your true monthly expenses.
  • Cut out everything you don’t need and aim to save at least 33% of your income.
  • Keep doing this for 3 years until you have 12 months saved up

Three years seems like a long time, but it’s a price worth paying. Half of your success as a self-employed entrepreneur comes from the preparation you put in before you quit your job.

Question 3: Am I capable of handling the stress and anxiety of being self-employed?

I thought I was a headstrong person. That is until I left my job, lost all my clients, racked up $26,000 in debt, and had no idea what to do next.

You and I are not immune.

Quitting your job and taking on full responsibility for your income, insurance, business regulations, taxes, and not to mention growing your business, comes at a steep mental price.

Are you ready for that?

It’s a tough question to answer when you’ve never faced real adversity. Before 2017, I would have said, “Psh, this will be easy!” Now here I am pleading with you not to quit your job until you are absolutely ready.

You will face adversity, it will cause anxiety, and you will need to deal with it in a healthy manner. If you don’t currently have constructive copping habits in place, may I recommend the following:

  • Begin and stick to a fitness routine. Go for a run. Lift weights. Do yoga. Have a healthy habit in place before you quit your job.
  • Practice some form of daily writing. Journaling is one of the best ways to build self-awareness. I write online but I also prefer to have an offline analog version (aka a nice Moleskine notebook).
  • Get enough sleep. Don’t fall for the hustle mantra. Your body needs time to rest and repair. Find ways to work more effectively, not more in general.

Question 4: Do I have a strong network around me?

Self-employment is lonely. For one, you don’t have your typical co-workers to gab with at random intervals throughout the day.

It’s also lonely because a lot of your friends and family won’t understand why the hell you quit your job. You need to find your people.

I have a mastermind group. We call it a mastermind group but we’re actually all really good friends who also happen to be self-employed. We hop on a group call every Friday for an hour. We’ve been doing it for the past 4 years. Every week I look forward to that one hour call because it’s the only time in the week that people get me.

Begin building your network. Yes, long time friends and family play an important role. But you need to find the people who are going through the same thing as you. Start connecting. Reach out on Twitter. Find people’s email addresses. Don’t be creepy. Be helpful.

You can’t go at this alone. You simply cannot.

Question 5: Am I prepared to accept the crushing reality that I’m trading one job for another?

Quitting your job doesn’t mean you’ll have more freedom. It means you’ll have a different job.

The over-sensationalized version of self-employment is you sitting on a beach while your bank account fills up from multiple streams of passive income.

For most of us, it’s not that easy.

We work to find clients. We work to service our clients. We work to create products. We work to sell our products. Before long, it’s easy to see that there is no difference between your new situation and the one before (besides the lack of a commute).

The grass is not greener on the self-employed side of the fence.

There are good days and there are bad days and the sooner you adjust your expectations the sooner you’ll actually be ready to quit your job with a clear head.

I hope this is the last quit your job article you’ll ever read

Before you storm out the door on your last day of work, I hope you’ve put 2 to 3 good years of preparation in.

If not, you’re in for a rude awakening.

Stop reading quit-your-job articles, all they do is make you angsty and impatient. Slow down. Ask yourself the five questions above and get to work putting the pieces in place.

Then, and only then, should you quit your job.

Want something more than your 9-to-5? Get my free new email course on how to build and launch a successful 5-to-9.

Written by

Stay-at-home dad. 9-to-5 escapee. Aldi aficionado. Connect with me here 👉

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