when to quit your day job

When to Quit Your Day Job

There are plenty of people on the internet imploring you to “quit your day job and follow your passion!” so you can have the life you want. They’ll tell you how they did it. How they earned 20k in one month. Now they have a fabulous life traveling the world without a care in the world. You can do it too!

This is some good old fashioned marketing bullshit.

Mostly, it’s candy-coated shit.

These freelancing cheerleaders are showing you the glossy side of things. Underneath those pretty pictures they paint are harder realities. Trying to get wifi in their hut in a remote location. The years of hard work they put in working for crappy clients. How they made very little pay for years on end.

Yes, honoring your values is important, critical even. Having the flexibility for the life you want is absolutely a solid reason for working for yourself. It’s just that, well, starting a business isn’t as easy as 1-2-3…fabulous life! 

It's true that some can start out making great money right away, particularly high in-demand folks like software developers. Others have to work much harder to build a sustainable and highly profitable clientele. Even for the former, it takes time to get the work you really want or making enough money from products to support you.  Sometimes your business is just a side gig to a day job. Even if you do work for yourself, in the early days it can still feel like having a day job.

I don’t want to dissuade you from working for yourself.

I’m just not one to varnish something up, sell you something that’s unobtainable or unrealistic. I want you to have the career freedom you seek. I know you can have it.

I could tell you to quit your day job tomorrow. I could tell you just believe that you'll get clients, that you'll build wings on the way down, float back, and be sitting on the beach sipping that umbrella drink while casually looking at your laptop.

You'd probably like me better. But most of you wouldn't find those magical wings sitting next to that fruity drink poolside. You might even end up like my colleagues who quit their day jobs the day after taking a coaching course, emboldened by the idea that they could "have the life they want!" tomorrow. Six months later, everyone who quit their day job to start a business was back in a full-time job, resigned to working for someone else the remainder of their career. Only one of them was still building her business — while working part-time. These failed business owners always stuck with me.

I don't want you to be one of them.

And you don't have to be. Knowing when to build on the side and when quit your day job can be tricky. Here’s a real world story about how a woman went from career beginning, to having a side gig to having the business she really wanted. 


It was the middle of a downturn. Jenni had just graduated from journalism school. Given the economy and state of her career, Jenni took a job writing for Construction & Demolition Debris Recycling Magazine. Hardly what she imagined when she dreamed of being a writer.

Even though she had zero interest in the topic, she saw the job as a good chance to learn, the work was fun and challenging. When she got into her thirties, she started having more chronic health issues. She was making a livable wage but was having a hard time building for the future.

The need for a more flexible schedule, and the ability to make more money led her to set out on her own. She had clients on her first day, including her former company which hired her as a freelancer. A couple of years in, she had a flexible schedule and was making money but she kept saying yes, even when opportunities didn’t align with her values. 

Around this time, Jenni came to me for coaching. Having her own business was much better but she was still writing about concrete. We set out to transition her work from well-paying but low satisfaction to one with more meaning.

She began writing about other topics in order to broaden her brand and to bring her work in more alignment with her values. She also created ChronicBabe, offering support and resources for women with chronic illness. It was a wonderful way to find more meaning and creativity in her work.

She paid the bills with work in the construction industry while blogging for no pay on her passion project. Over time, Jenni began getting asked to consult and to speak at conferences about health issues facing young women.  She felt torn between the work that paid her and what she really loved to do. She wondered if she could make a living working on ChronicBabe. Then her marriage started to fall apart. When the economy tanked again she found herself living alone in an apartment with almost no work, and her symptoms going bonkers. She worried about paying for her health insurance.

Debt was piling up. She was terrified. 

This was one of those moments most solo business owners face, wondering if you should go and get a real full time job. Give up the dream. She deeply considered getting a good old fashioned day job. Instead, she took a bunch of writing gigs that she hated. The situation was frustrating but did the best she could. Though she worked for herself, it was more like a day job.

She kept working on ChronicBabe on the side.

The letters she received from readers were so heartfelt that they moved her to continue working on the site. 

While the day to day hustle was physically and mentally exhausting, Jenni also felt liberated. After a year of steady work with a client that was 80% of her revenue, the organization suddenly had a change in their client load. The work stopped, leaving her scrambling to fill in her pipeline. She decided this was it.

She was never going to hustle like this again.

After that, her side gig became her focus, deciding that everything she did had to be tied to it, only taking work that was related to ChronicBabe. Jenni quit her "day job" 8 years after she started working on her passion project.

Depending on your circumstances, it may not take you this long.

It might take less. It might take longer.

When Jenni first started her side project, she had no plan to drive revenue. She wasn’t trying to make money. She started ChronicBabe because she really believed in it. During the first five years of ChronicBabe, she lost money. When she decided to make it her life’s work, she started to think about how to drive revenue. She began by booking speaking gigs and did consulting.

Over time she created new products like a monthly subscription program which included a series of emails on critical topics, webinars, a huge resource PDF and a private community. Today 50% of her revenue comes from the subscription service, 20% from speaking engagements and 30% from consulting that is related to ChronicBabe. She’s currently at work on an ebook and anticipates that next year the subscription program will be 70% of her revenues.

Jenni's story demonstrates that you can build a meaningful life and business working for yourself. Though she worked for herself, Jenni’s writing in the construction industry was like a day job. Jenni was able to quit her "day job" by:

When to Quit Your Day Job

Be like Jenni, not like my former colleagues. Don't quit your job and then begin building your product. This is the surest way to failure. Businesses take time. Build and nurture those little seedlings now while you have the security of your day job.

The reality is, only you can truly know when the time is right to quit your day job. Here are a few questions you might ask yourself when at day job vs. business crossroads:

- Is your idea clear? Or is it still fuzzy?

- Are you ready to commit to your idea? Or are you still dabbling?

- Are you emotionally, mentally and financially ready to handle the ups and downs?

The answers to these questions will tell you whether it's the right time to quit that day job or whether you need to keep building on the side. But don't be afraid to take your time.

A sustainable business doing meaningful work is worth the wait.