When Should I Quit My Job?

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When Should I Quit My Job?

How badly do you want to quit your day job so you can work in your business full time?!

If you’re a side-hustle entrepreneur who’s still working a full-time job you’re probably asking yourself, “When should I quit my job?”

Friends, you are asking the wrong question!

Over the past 20 years, I’ve watched many entrepreneurs set 'leave my job' as a business goal only to reach it and then watch their business dry up.

They were so focused on leaving their job that they weren’t looking five and 10 years ahead into how they would keep their business growing over time. Because they weren’t looking further down the road, they didn’t have a plan in place to get there which means that they weren’t building a solid foundation to support further growth after they left their steady paycheque behind.

The more important question you need to be asking yourself is, “Where am I going?”

Leaving your job needs to be a side effect of your business growth. Leave your job when your business demands your full-time effort in order to grow to the next level.



Open up a document and copy and paste these 4 questions in so you can answer them when you’ve finished reading this blog:

  1. Where do you want your company to be in 5 years? In 10 years?
  2. What other services, products, locations, etc will you add on?
  3. How will you scale for faster growth, robust revenue, and hopefully, less effort?
  4. What is your evolutionary vision for your company? For you as a business owner? For your life?

Start thinking beyond just leaving your job (don’t be basic!) and think about your BIGGER, BOLDER VISION for your life!

Remember: Entrepreneurship is a tool for creating the life of your wildest dreams.

When done right, entrepreneurship will (eventually) give you the freedom to do what you want, when you want, where you want, with who you want!

(It’s still gonna take a few years and a lot of focused, intentional, sometimes scary work)

You need to start thinking about your business in years, not months.

I find that most entrepreneurs fall into two camps:

1) Those who want to build themselves a 9-5 job where THEY get to be their own boss

They’re keeping it simple and showing up to do the job then getting back to life. They’re most likely focusing on a single product or service they can deliver directly, like a web designer, personal trainer, freelance copywriter, or therapist

2) Those who want to build an empire with a vision far beyond what they are working on right now

They’re working towards building teams, subcontractors, and other professionals who can help scale their business into something huge and far-reaching. They’re exploring several revenue streams including passive revenue and various products and services. They’re also likely getting active in the content marketing game, YouTube, Podcasts, Blogs and of course social media like TikTok, Instagram, LinkedIn and Facebook.

Both are totally valid and whichever camp you choose will be based on your vision for your life, beyond entrepreneurship.

It’s super important to know which camp you fall in because it will impact your offerings, sales flow, and business development strategy (how you get customers and make money).

It will also dictate what you MUST do and what you can ditch as you enter the world of digital marketing and content creation.



If you fall into the empire-builder camp:

  • What is your big, bold vision for your company 10 years from now?
  • 20 years from now?
  • What new services or products do you see yourself adding on?
  • Do you see yourself writing a book, speaking on stages around the world?
  • Being interviewed by your idols because of how badass you are?
  • Maybe you want to host giant conferences or intimate retreats?
  • Perhaps build a large community impacting millions of people around the world?
  • How about millions of followers on social media with ridiculously fun collaborations with some of your favourite content creators?

Or, if you’re like me, maybe you want to have a kickass team doing most of the heavy lifting on the behind-the-scenes work and you can spend your time creating fun content online and travelling around the world to work, play, and connect with interesting people!

Get clear on your big, bold business vision and reverse engineer the steps you need to take there.

You want to envision your 10 and 20-year plan for your business (and your life) and then reverse engineer your goals into an action plan for each year.

It’s about looking at your business plan in stages and breaking down what you need to do and the foundations you need to build for each stage to get you to the next.

For example, when I wanted to create a scalable group coaching program like my 12-week Radical Revenue Accelerator, I first needed to develop my signature program.

Developing a signature program meant I needed time in the field working with folks and perfecting my own process, so I could distil it into an effective and successful online program.

I also needed to establish my own reputation, credibility, and track record of results.

Plus, I needed to build a community of folks who were aligned with and needed, what my program offered.

All of this required connecting with the right people and perfecting my own sales process so I could actually work one-on-one with folks in order to perfect my process.

I also needed to spend time building and nurturing my community and building my brand recognition and reputation out in the world, which in my case started with hosting monthly events and speaking all over the place and a massive amount of networking!

Then, it flipped into showing up online, creating a community for new entrepreneurs and hosting online events, public speaking to the right audiences, and creating content like blogs, podcasts, YouTube videos and more.



This was the crucial Growth Stage of my business journey where I proved my business idea had legs … people not only needed what I was offering, they wanted to pay for it!

If you’re in the Growth Stage you’re gonna be doing a whole lot of work, including:

  • Tons of experimentation and trial and error to uncover what people want
  • What works at converting strangers into customers
  • Mapping out your personalized sales flow

And you’re going to be hanging out in the Growth Stage until you generate $100,000 in revenue from your best seller … the big idea you want to Scale!

You’ve probably heard me reference the Idea, Growth and Scale Stage of business before.

Do you know what stage you’re in?

Idea: You’re still playing around with what your business is all about. You're figuring out your business name, niche, branding, and offerings. You’re less than a year into your business and have generated less than $25,000

Growth: Your business is up and running. You know your niche, and offerings, and have even landed a few customers. You’re still figuring out your sales flow (how to get customers quickly and easily) as well as your position in the market and the types of content your market resonates with the most. You’re starting to get busy and figure out your “thing”. You’ve not yet generated $100,000 in revenue based on your top seller.

Scale: You’ve nailed down your top sellers. Customers flow to you quickly and easily. You know your unique position in the market and are creating content that converts strangers into customers. You’ve surpassed $100,000 in revenue, are getting ridiculously busy, and are ready to explore passive revenue streams, outsourcing to virtual assistants, social media managers and other professionals, and you’re probably ready to invest in marketing and advertising. It’s time to work less and play more!

The Idea to Scale journey is typically 5-7 years, depending on:

  • How much time you have to give to your business and those RGAs, Revenue Generating Activities
  • How quickly you uncover what works and what doesn’t, and pivot as needed
  • How much you let fear and perfectionism stop you from taking action

A common time frame for moving from Idea to Scale looks like this:

Idea Stage: 6 months to 1 year
Growth Stage: 1 to 3 years
Scale Stage: 2 to 3 years



Wait … not 6 months like (almost) every single online business expert promises??

I hate to burst your bubble friends … no!

I have yet to meet an entrepreneur who’s gone from zero, not even an idea, to scaling their business into passive revenue streams and hiring teams to do the heavy lifting while hitting six and seven figures in 6 months.

Most entrepreneurs haven’t even gotten over their fear of doing a Facebook live or doing a sales call in six months.

No shade.

It’s part of the learning process.

I’m telling you right now if you’ve never built a business before there are very specific skills you have to learn and master … not to mention the internal blocks to success you’ll have to work through.

Ooh, there’s that tough love wrapped in sugar y'all keep talking about!

Can you see how you can’t just build a website, come up with a catchy name, snap your fingers and POOF you’re rocking and rolling in your business and you can kiss your boring job goodbye?

You need to break down your own Big, Bold Business Vision into stages and then think about how you’re laying the foundations along the way.

Then make sure your daily business activities are serving your current stage of growth

It’s important to get in the habit of consistently checking in to make sure you’re not doing things in your business that will take you off course of your current stage of growth.

If you’re in the Idea Stage, focus on that market research. 

  • Get up close and personal with the folks you want to work with
  • Test content to see what resonates
  • Get your first offering up and running so you can start selling it!

If you’re in the Growth Stage, focus the bulk of your time on your RGAs.

My 4 Fast & Free Revenue Generating Activities are networking, public speaking, community building and list building & SEO-friendly content creation.

Your objective in the growth stage is to … GROW!

  • Grow your audience.
  • Grow your list.
  • Grow your customer base.
  • Grow your revenue.
  • Grow your reputation.
  • Grow your network.

Grow. Grow. Grow.

I want you to spend your time growing the things that matter so you can get yourself to $100,000 fast!

If you’re in the Scale Stage it’s about bridging your high-touch RGAs into automated systems.

  • Outsourcing your busy work
  • Leveraging sales funnels and content marketing
  • Turning your top seller into something passive and scalable

So you can earn more while working less.



Now, back to quitting your job.

Let’s get real about leaving your job to be a full-time entrepreneur.

There are times when leaving your job may be necessary.

For example, if you’re working in a toxic environment and it’s affecting your health and quality of life. Or if your job is literally taking all of your time and energy, leaving you with nothing left to give your company.

In these cases, you may decide to find other work or something part-time or less demanding so that you have more to give to your company, but still provides a steady pay-cheque so you can still pay your bills without unnecessary pressure on you and your business.

You may also have financial support outside your job and leaving it to focus on your business is doable. To this, I say, make sure you have a plan and a solid Revenue Generating Activity strategy so you know exactly what to do every day to grow your business.

Also, understand that it takes time to grow your business and a steady income stream.

It always takes longer than you envision and more money than you think to get a company off the ground.

  • Operating expenses
  • Professional services
  • Events and memberships
  • Clothing
  • Travel
  • Health expenses if you no longer have coverage from your job.

If you have enough funds to support you for at least 2 years outside of your business AND you know what to do or are working with a business coach to guide you ... go for it!

If you’re not used to generating your own sales and keeping your calendar full of revenue-generating activities on your own, you risk becoming one of those entrepreneurs who leaves their job then twiddles their thumbs, writes their 20th blog or creates their 50th TikTok but aren’t bringing money in ... then it's right back to the 9-5.

Having a job, even something part-time, to pay your bills while you figure out your own biz can be a life - and business - saver.



Let’s talk about The Great Resignation!

You've been working from home for almost two years now and have noticed a marked improvement in your mental and physical health.

You're no longer spending stressful hours commuting every week. You've got more time to play, spend time with friends and family, or focus on self-care.

You're saving a ton of money on parking, gas, transit, meals, and clothes.

And no more obligatory office parties, difficult co-workers, or pants!

Suddenly your boss is demanding you come back into the office and give up all your freedom and contentment. 

OR you’ve put two-and-two together and realized your boss is farming out your skills and experience at top dollar to their customers while you get paid a fraction of what your skills are worth. 

You're sick of working for pennies while your employer charges a premium for your labour and wondering if there's a fairer way to get paid for your brilliance. 

I’m going to share a controversial opinion and it may ruffle some feathers.

If you have skills, expertise, or experience that other people want, working for a corporation instead of yourself is for suckers.

There. I said it. Don't shoot the messenger. 

Think about it.

Your employer farms out YOUR expertise at a premium rate to THEIR customers while paying you a fraction of what YOUR expertise is actually worth.

Not to mention, the cost to learn and develop those skills was all on you and may very well still be haunting you by way of student loans.

Does that seem fair to you?

Now, let’s bring in a bit of nuance. I get it. It’s not as simple as having marketable skills.

Building a business is a lot of work and is inherently risky, as many entrepreneurs experienced at the beginning of the pandemic.

Hello Great Pivot of 2020

But let’s get back to The Great Resignation.

So many people are waking up to the scam that is working for an employer instead of yourself.

If you’re courageous, up for a challenge, and can handle uncertainty and feeling your way in the dark as you create something amazing … you’ve GOT to give entrepreneurship a try.



And if you’re going to make the leap into entrepreneurship, make sure you make room in your budget to invest in someone who can show you the ropes and teach you how to turn your brilliance into a profitable business.

You might want to invest in joining my 10-week, Radical Revenue Accelerator.

The accelerator is for service-based entrepreneurs who are sick of farting around on busy work that doesn't work and ready to learn REAL marketing and sales skills for getting clients and making money!

We spend 10-weeks together LIVE on Zoom (this is NOT a self-guided course) and we focus on using the power of social media and other online tools like content marketing, sales funnels, and automations so that technology and the internet do 50-80% of the work for you!

Check it out here!



Back to when it's the right time to quit your job.

  • You’ll know it’s right the right time to leave your job when:
    • You’ve got a solid system in place that is effectively bringing in revenue (even if it’s not quite enough to live off yet)
    • When your biz is at a point where it can’t grow anymore without your full-time attention.
  • If you’re part of The Great Resignation don’t eff around!
  • Invest in someone who can teach you how to get your business off the ground and making money.
  • Leaving your job should be a fun perk or side effect of your biz growth ... not your goal.
  • Think about your business in terms of years, not months
  • What is your Big, Bold Business Vision?
  • Start with a 5-year plan and reverse engineer an action plan for each year that will take you from the Idea Stage through to the Scale Stage

Think bigger, dream bolder, and plan the heck out of the next few years to make it happen!

Until next time, happy connecting! 

I'll see you online, 

Lindsay 😘





Find out exactly why you're not growing and discover simple consent-based marketing and sales skills for attracting fabulous new clients!