How to Know When to Leap from Your Day Job to Your Business

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How to Know When to Leap From Your Day Job to Your Business

In the movie Divergent, Tris, the hero is, well, divergent. She chooses Dauntless as her faction. In making that choice, she goes against her family tradition. Yet she’s excited to start her new life.

To move forward with Dauntless, she has to jump onto a moving train. That’s just the beginning.

To get off at Dauntless headquarters, she has to leap off the moving train to the top of a building.

Just when she thinks that’s the last leap she has to make, the trainer tells the new initiates that they have to jump again!!!!

This time, off the edge of the building into a dark hole.

Business building is like Dauntless initiation.

There are many leaps to take. Some are small and indiscernable, like choosing daily to create content when you could be watching Scandal.

Some, like leaving your day job, are HUGE!

So, let’s swallow the big frog first. One of the most asked questions I get from ThinkUp clients working in corporate is, “How do I know when to leave my job?

It’s as easy as 1, 2, 3…

Step 1: Pick a Date

Picking a date forces you to draw a line in the sand.

On the other hand, when you set a goal like, I will leave when I have $xx,xxx, things come up for you to do a back and forth dance. They’ll seem like good reasons, like your car stalling and needing a $1,000 fix.

When you pick a date you have something to work towards. There is an end in sight. You begin to see the light at the end of the tunnel.

It energizes you.

Now the question is, “What date do I choose?

Most of my ThinkUp clients can leave anywhere between 6 months and 2 years. It depends on where you are in your business and how prepared you are to leave.

Which brings us to step 2…


Step 2: Get Prepared

Now that you have your date, it’s time to get prepared.

You’ll need to replace 3 things before you take the leap. I call them the 3S’. Most people think of salary right off the bat. However…

Leaving your job is more than a money game. It’s a confidence game.

In addition to replacing your salary, you’ll also need to replace structure and support.

Let’s break it down.


According to Alan Weiss of Million Dollar Consulting, a good benchmark for replacing your salary is to have 1 year of living expenses + 6 months business expenses + 10% contingency.

Before you freak out, living expenses don’t equal your current salary. Living expenses are food, shelter, and transportation. That’s it!

It’s NOT the latest phone, gadget, shoe, cable or cruise.

Once you have your number, there are several ways to get there.

The BEST way to reach your number is with your business income. You accomplish 2 things with this method: creating your cushion, and validating your business idea.

Saving is also an option. Trimming your expenses is really helpful for this option. It will also build healthy spending habits for when you leave the corporate world.

Crowd funding is a popular way to fund your business, particularly if your are selling products. Crowd funding works by tapping into your network and asking them to invest in you and your idea. The great thing about crowd funding is that folks get to sample your product or service and rave about it on social networks. Can you say testimonials?

You can also fund your transition with credit. I’m not a ‘debt is the devil’ type of gal, nor am I a ‘leverage everything’ gal. Credit is an absolute last resort.

It’s likely that you’ll use a combination of ways to create your cushion.


Why is structure important?


Structure is about taking consistent income-generating actions. Consistent income-generating actions lead to consistent income. Consistent income leads to increased confidence. Confidence, my friend, helps you take the leap.

“But Nneka, what are income-generating actions?”

Income generating actions are daily actions that build your audience. They include posting on Facebook, commenting on a blog posts, attending networking events, connecting through calls, sending personal notes.

While you’re out cultivating your audience, take the opportunity to learn what your clients want and need. Talk to them about their challenges meeting their goals and about what’s driving them to meet those goals.

Your audience is aching to tell you what they need. When you create products and services that meet their needs, you generate consistent income.

There’s a bonus!

Everyone isn’t going to be a client, BUT, they can be partners. Partners are golden because they help you get the word out and they’re a great referral source.

Building partner relationships lead to guest blogging, interviews and speaking engagements. Now we’re talking exponential audience AND income growth.


If you’re like my clients, you HATE support.

I get it. I hate support too. We hate asking for help. We LOVE saying, “I DID THAT – all by myself!

You have good reasons. You’re hella smart, self-motivated, and an expert in your field. On the dark side, you think of getting support as a sign of weakness.

Thing is, when you take the leap from corporate into your business, support is your air. It enables you to soar, as opposed to free fall.

Usually, support comes from friends and family, but they’re probably looking at you sideways. They’re likely the ones asking you why you want to jeopardize your “good” job to pursue your dreams.

You can also get support from accountability partners, masterminds, mentors, and coaches.

Once your salary, structure, and support is in place, it’s time.

Step 3: Take the Leap

Your day is here, but you don’t feel prepared.

I’ll share a secret…I didn’t either.

I had everything in place – savings, my habits, website, even client success stories. But I still felt like I needed to stay. So I did…for 6 more months.

Fortunately, I was in a group coaching program at the time (support). I went to the group with the usual question, “Is it time?”

What I heard was, it’s never time.

You never feel prepared enough.

It’s never perfect.

The stars don’t all align.

What does happen is that your dream begins to get smaller. You start to settle. You shrink just a little bit every day.

You see, you are ever-expanding. You can’t change that. You are growing whether you like it or not.

When you try to keep your bigger self in your tiny box, things get uncomfortable – even painful.

It doesn’t have to be that way. Your day is here. You can step forward. You can step into the person you’ve already become.

You feel a bit vulnerable.

You open up some more, and…YOU JUMP!

What happens after – as you continue to grow and open?

You FLY!

Nneka Kelly, Woo Biz Coach
Nneka works with budding holistic practitioners and Woo Biz Owners to honor your intuition while creating systems to grow your business.

2 Responses to “How to Know When to Leap from Your Day Job to Your Business

  • Great post, Nneka!!

    I’ve taken that first step and selected a date, which I’m very proud of. I have been back and forth about this for the longest time! So, now I’m super motivated to get myself in gear!

    Thanks for sharing!