Should You Quit Your Job and Start a Business?

JessieStarting a Business Leave a Comment

So, you’re thinking about starting a business. Your day job is getting to be too much, and you figure it’s now or never.

That might be the case. But after quitting two different jobs to start two different business, I’ve learned a thing or two about what you really should be taking into account.

But first, a warning: These are not sexy questions. There are a million people who are ready to tell you to just follow your heart, quit your job, chase that dream—likely so they can profit from you in some way. I want to give you the real questions you need to take into account before taking the leap.

Watch the full video here:

Question #1: Have you done EVERYTHING possible to make the situation better?

Ugh, I know. When you hate your job, this is the last thing you want to hear.

But hold on. I’m speaking from experience here.

Sometimes, you don’t need a drastic change. You might be surprised how focused changes in your current work situation could create a vastly more enjoyable job. This might mean:

  • Going after a promotion, or even a lateral move to a different department
  • Asking to work from home
  • Changing your work habits so you’re more productive
  • Changing how you show up at work so you’re more respected

Learning how to course-correct in your job is a vital skill. And if you don’t learn it now, starting a business isn’t going to fix it. The moment things start going south in your new business (which is guaranteed to happen at some point in your startup journey!), you’ll want to jump ship.

So try to fix things first. If you give it your best efforts and you still hate it, good—now you can move forward knowing it was truly unsalvageable.

Question #2: Do you need to start a business?

…Maybe you just need a different job.

If you’ve had limited work experience, or you’ve been in the same industry for a long time, a job change could be a much easier fix than starting a business.

We’re after a solid income and joy in our work, right? If you can save yourself the headache of starting a business and find those things in a traditional job, awesome. There’s not actually some badge of honor for freelancers and entrepreneurs.

Your current skills could be applied to a vastly different kind of job. For example, if you’re a salesperson with high emotional intelligence, where could you use that? Maybe you could get a job promoting a college at school fairs. Totally different change of pace. Are you a web developer for a small business? Maybe you could sign on with a huge consulting firm—the kind that sends you around the world on their own dime.

Hate the commute? Maybe you don’t need to start a business—you just need a remote job.

There are lots of jobs out there. If you’re just after some time to travel, a higher income, or a more relaxed working environment, it’s likely you could find one inside an existing company with a lot less stress.

…But maybe you know that’s not for you.

I quit two different jobs specifically to start my own businesses. The second one especially was, by all accounts, an ideal job.

But for me, it wasn’t about running away from a bad thing in favor of a good thing. It was a desire for a totally different lifestyle—and the good and bad things that came with it.

I wanted total ownership over my work. I wanted the business owner experience.

And maybe you feel that too. In which case, I have one more question for your consideration:

Question #3: Do you have to quit your job to build your business?

For most people, the answer is actually no.

In fact, you might be in a position where you CAN’T quit their job until your business is bringing in some money.

So what do you do? You make time. This might mean:

  • Working in the evenings, after you’ve taken care of family responsibilities
  • Waking up early to make use of your best hours
  • Changing jobs to something less demanding so you have time to build your business without the stress of losing an income
  • Talking to your partner and asking them to help you make and protect the time you need to get your business off the ground

Building a business this way is fantastic because it allows you to test your business and grow it without the stress of losing an income.

But again, that’s not for everyone


You see how we’re getting narrower and narrower, right?

If you get to this point and you’re thinking, “I just need to quit the job, start a business, a deal with the consequences,” then that’s 100% your choice.

The first time I made the leap, that was exactly my situation. And it worked—for a while. Though in all honesty, I didn’t know how to course-correct. So when things wen wrong, I threw in the towel and went back to a traditional job.

The second time, I went slower—doing some exploratory work for some clients for free while I was still employed. Getting testimonials. By the time I launched, I had a clear direction and some good experience under my belt.

Both times I had financial padding to give me a few months of runway time. Even when you take all the right steps, building a business takes time. Don’t go in without a plan.

So, tell me…

What’s your plan?

Are you going to quit? Will you make your current job better? Somewhere in the middle?

Share down in the comments!

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