Actually Quitting a Job is Easy. It Doesn’t Mean You Should.

Consider these 5 questions before you quit too

I hopped onto Teams and waited for my manager. I felt like a panda tip-toeing into the Colosseum.

All I needed now was the tiger.

I’m f*cked.

“Hi, Scott.”

I nearly dropped my bottle and said hello back.

“Well, Scott, I knew this was coming, but the timing caught me by surprise. I was hoping you’d stay a little longer…”

Here we go.

“But I’m happy for you.”

Wait — what?

I thought she’d shout. I thought she’d be angry. I thought I’d have to grovel.

I’d just dropped the R bomb — that I’m resigning to become a freelance writer and travel the world — and my manager is happy for me.

It’s almost too easy. You hand in your notice and the wheels are in motion.

But this doesn’t mean what comes next is easy too.

Before you quit your 9–5, here are five questions to consider.*

*First, the footnotes…

I’m privileged

I’m twenty-something. I’m male. I have no dependents. My first language is English. I went to university. I have a supportive girlfriend and family. I live in the UK’s happiest town.

I lucked out.

I have a specific set of skills

I’ve worked in SEO for three years. Because of the pandemic, SEO professionals are in high demand.

Companies are throwing themselves online.

Question #1: Why do you want to quit?

Are you quitting because you’re bored?

Are you quitting because you don’t like your boss?

Are you quitting because you don’t like your company?

These are all okay. I’ve been there.

In fact, there’s no right or wrong reason.

Just because it gets tough, though, it doesn’t mean you should throw in the towel — at least not right away.

No job is perfect. Each has its challenges.

But if you really want to try something else, here’s the permission you’ve been looking for.

The 9–5 isn’t going anywhere.

You can always jump back.

Question #2: Do you have a plan?

I’m not talking about a life plan.

I’m talking about the next six months.

How are you going to bring in money? Do you have experience with the thing you want to try? If you have savings, what’s your runway?

I’ve been freelancing on the side since November 2021. It’s steady, it’s consistent, and I like it.

That’s why I’m confident about scaling up.

If you don’t have this confidence, keep hustling on the side. Try stuff. Taste stuff. Build passive, scalable income streams.

I’ve shared my work openly —both the highs and lows. My family has seen it all.

That’s why they’ve been supportive.

They’ve seen I can make it work.

I also shared my three-year plan with my family before I quit my job. They gave me feedback and pointed out my blind spots.

My plan details the following:

• Steps to achieving my one-year goals
• My life goals and travel plans
• My weekly task list

Question #3: Are you financially secure?

I can’t stress this enough:

When you haven’t got a regular paycheck, sh*t can get scary real quick.

I recommend having at least six months of savings in the bank. Think of it as an emergency fund.

Don’t touch it.

Just let it sit.

In other words, if you’re spending $3,000 a month, have $18,000 in your account.

With the best will in the world, things might not go to plan. Those clients might not land. You might get sick.

You’ll also want to think about your monthly expenses: rent, bills, living costs, etc.

Don’t get burned when it’s avoidable.

Give yourself time.

Question #4: Are your plans realistic?

When I launched my podcast, I thought I’d rake in the money.

1,000 downloads per episode? In three months?

Piece of cake.

I dreamed of landing sponsors and making four figures a month.

Two years in, that hasn’t happened. My most popular episode has 351 downloads:

Admittedly, the pod’s taken a break. (It’ll be back in November.) It could also reach these numbers further down the line.

Nonetheless, I underestimated how long it takes to build an audience. If no one knows you, it’ll take even longer — no matter what the thing is.

I had the same experience with a webinar I hosted.

Only one person showed up.

It’s easy to fool ourselves. To overestimate. Just remember that the numbers don’t lie.

Test, test, test. This is the only way to find out if your plans are realistic and enjoyable.

The same goes for your day-to-day routine. Is the lifestyle you’re seeking an escape, or is it sustainable? Take a week off work. Try the thing you want to do when you quit your job.

See if you like it.

Last month, I lived with my girlfriend in New York.

As she worked, I upped my freelancing game, and I realised I could see myself doing it full-time.

It was a helpful dummy run.

Question #5: If things don’t go to plan (heaven forbid), can you get another job?

Try Tim Ferriss’s fear-setting exercise.

It goes like this.

Once a week, spend 10–20 minutes writing down ten of the worse things that could happen when you quit your job.

Next, write down ten ways you could prevent the worse things from happening.

Finally, write down ten ways you could repair each bad thing.

The practice will help you realise how deceptive your fears can be. Face them head-on and see their point of view.

They soon disappear.

Here’s a free template in case you’re interested.

One of the best ways to soothe these fears is to get another job.

(This doesn’t mean you have to keep it.)

Earlier this year, I was making my biggest online course to date. I felt uncomfortable. Not much money was coming in.

I decided to get another job.

I jumped on LinkedIn and reached out to recruiters. One week later, a manager role landed at my feet. It was three days a week and offered a better salary than my previous job.

LinkedIn and recruiters are your friends.

Seek them out.

Now again, I know I’m a privileged twenty-something. I have no dependents…

It may not be as easy for you to get another job.

If you have in-demand skills, though, and you up your LinkedIn game, you’ve got more than a shot.

Takeaways

Even if you quit without a plan, you’ll probably be okay.

You might get burned, but you’ll survive.

Most situations are recoverable.

However, you’ll feel emotionally safer by considering these five questions before you quit:

• #1: Why do you want to quit?
• #2: Do you have a plan?
• #3: Are you financially secure?
• #4: Are your plans realistic?
• #5: If things don’t go to plan, can you get another job?

Your future happiness depends on you. No one else.

Go get it!

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