Skip to content

Should You Quit Your Job to Start a Business?

contemplating job to start a business

“Your days are numbered. Use them to throw open the windows of your soul to the sun. If you do not, the sun will soon set, and you with it.”
– Marcus Aurelius

The Fantasy of Owning Your Business

Ah! Owning your own business! Freedom to do what you want when you want. Cool office spaces, teams having a blast, and unlimited financial rewards. According to a Zapier study, 61% of Americans have a business idea mulling around in their heads.

We tend to romanticize ideals of what running our own business, being an entrepreneur, will look like. But, before you tell your boss to take this job and…., I’m going to ask you to assess yourself: Are YOU ready to leave a job physically, emotionally, and financially?

Is the Timing Right to Quit and Start a Business?

If you’ve tested your business idea and have done your due diligence, then the best time to start a business is almost always NOW, whether you’re reading this during a recession or a boom.

When to start has little to do with how the Dow Jones Index is performing and has everything to do with how you’re performing — specifically, whether your temperament is up for the challenges of running your own business and whether your personal life (relationships and finances) will support you. It’s best to start a business when you’re not in crisis mode and when a single sale or client won’t make the difference between eating and starving.

Even with ample savings, a solid idea, and tons of social support, you’ll want to get comfortable being uncomfortable. Starting and building a business that meets your income needs takes time. If you have a secure job or steady source of income, use that security to your advantage by building up savings to cover the transition.

You Don’t Need to Immediately Quit Your Job

By the way, you don’t have to fully transition if you don’t want to, so don’t let that force your decision. Check out Side Hustle or Full-time? – Vetting Your Business Idea, Part 1

Do You Have the Mindset of an Entrepreneur?

Every so often, I have a day where I miss being just an employee — able to take a sick day, punch-out and forget about a crisis until the morning, or just let my boss make a huge decision instead of me. But most days I love being an entrepreneur.

That said, do you have the proper business-owner mindset? When you’re an employee, it’s easy to focus on your tasks, work with your department, and then blame lazy Joe or the other team when everything hits the fan.

But when you’re the entrepreneur, you’re wearing most (if not all) of the “hats”, at least in the beginning, and bearing all the responsibility. Projects going wrong, irate clients, or unexpected sales issues all fall on you. Make sure you are mentally prepared to accept the full weight of these duties.

How Do You Prepare?

Not to scare you, but there are things to consider, real-world scenarios that you need to prepare for before you make the jump.

Stoicism, the philosophy of the Stoics, believes in mentally rehearsing the absolute worst events possible. In his TED Talk Why You Should Define Your Fears Instead of Your Goals, author and entrepreneur Tim Ferris gives us a Stoic methodology for preparing for these situations:

[Seneca the Younger lead me to] the exercise Premeditative Milgrom, which means the premeditation of evils… in simple terms, this is visualizing the worst-case scenarios and details that you fear, preventing you from taking action, so that you can take action to overcome that paralysis.

In other words, Premeditative Milgrom is the practice of anticipating all that could go wrong and brainstorming all the ways you could avoid those outcomes. But in business, sometimes the worst happens anyway, so you can also use this practice to also devise various plan Bs.

In his talk, Tim gives us the specific exercise he uses: Make two columns on a sheet of paper. In the first column, write the worst thing that could happen. In the second, “… write down the answer to what could I do to prevent each of these bullets from happening or at the very least decrease the likelihood even a little bit.”

So consider some of the very real possible negative circumstances and decide on mitigating solutions in advance. Here are some you might consider with possible solutions in parentheses:

Negative business circumstance Mitigating solution
You’re calling clients to collect and they’re not responding Call them from another number

Send a demand letter in accordance with local laws

Talk to a debt-collecting attorney to create a best-practice procedure

You’re knocking on doors and you’re getting rejections Take a sales course

Hire a sales consultant

Do more research and adjust your approach

You want to hire the best talent but can’t afford it Make a partnership offer

Investigate fractional consultants


You want to get an investor or a loan, but you’re not approved Research alternative funding sources

Tap into your network for help

Crowdsource your funding

You have payroll coming up in two weeks and you have mouths to feed and staff and their families and you don’t have enough cash in the bank to process payroll Talk to your banker about lines of credit

When you’re in a position, create a rainy day liquid fund for similar circumstances in the future

By coming up with solutions in advance, you can stop those endlessly cycling thoughts from filling you with fear. Which leads us to…

How Do You Take the Leap (a.k.a. Overcome Fear of the Unknown)?

One time I tried parachuting. No matter how much I psyched myself up, when I was finally standing in the back of that small plane packed with other skydivers, the instructor shouting over the roar of wind blasting past the open door, I felt terror. I was first in line, and I saw the miniature world lying 10,000 feet below us.

When he said, “Go!” I had no choice. I had to jump or we’d miss the target zone.

Here’s the funny thing: the scariest part was the split second before I jumped. When my chute opened, I felt a serene sense of awe as I took in the beautiful landscape in near silence.

Nothing will take away your fear. You can be fully prepared, have 20 years worth of savings, and a rock-solid business plan and the fear and uncertainty will remain.

Key Takeaways

Anyone who wants to run a successful business needs to be prepared to learn, fail, and stick it out through the tough and ugly times. Accept that it will be difficult, and you will be better prepared to find success.

  1. Cultivate the mindset of a business owner – take responsibility (and blame) for all results
  2. Prepare: Make a list of the things that could go wrong and look to avoid and/or solve in advance
  3. Take the leap. The scariest part is right before you do. The leap is the only cure.
Feras Alhlou

Feras Alhlou

Feras has founded, grown, and sold businesses in Silicon Valley and abroad, scaling them from zero revenue to 7 and 8 figures. In 2019, he sold e-Nor, a digital marketing consulting company, to dentsu (a top-5 global media company). Feras has served as an advisor to 150+ other new startup businesses, and in his current venture, Start Up With Feras, he's on a mission to help entrepreneurs in the consulting and services space start and grow their businesses smarter and stronger.

Related Shorts

Before Taking The Full Time Entrepreneurship Leap, Be Prepared

2 reasons why people don’t learn

My Biggest Regret In Life

The Damage of Mislearning

Cowards Never Live

Advisors NOT Therapists

Double Dipping the Economy

Who Your Real Business Enemies Are

3 Types of Side Hustles

Success is 90% Work

High Expectations – Low Resilience

The Only Manager Steve Jobs Had

Waiting for the Perfect Job 👴🏼👵🏾

How to Build a Unicorn

Eating Glass and Staring Into the Abyss

Help Paralysis

When Feeling Down

Collecting Books and CDs

Sir Richard Branson on Hard Work

But I Worked Hard…

Panicking Over Normal Business Things

How to Rechannel a Client’s Energy

What Is Aikido?

Andy Grove on Business Principles

Don’t Abuse Your Power

Why Are You Proud of That?

Glorifying Business Mistakes 👎👎👎

Procrastinating Starting Your Business

Ponzi Schemes in 2024

How to Take In Client Rejections

Once in a LifeTime

From Laid Off to an 8-Figure Acquisition

3 Reasons You’re Stuck in the Rat Race

I Have a Dream But

The Entrepreneurial Drive

6 Reasons Stopping You From Starting Your Business

Why Business Advisors Don’t Take You Seriously

How to Overcome Fear of Failure in Business

THE REASON You Haven’t Started Your Business Yet

Charlie Munger’s Key to Intelligence

Business Is Not for the Lazy

The Mental & Social Burden of Failing a Business

Don’t Compare Your Chapter 1 to Their Chapter 20

The Power of Gratitude in Entrepreneurship

The Power of Gratitude for Business Culture

Entrepreneurship Is 5x Harder than You Imagined

When to Keep Going or When to Quit in Your New Consulting Business

After a Layoff, Reflect – Improve – Restart

Laid Off? Starting a Consulting Business Is Like Looking for a Job

Starting a New Business: Are You Ready, Willing, and Able