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The #1 Reason You Haven’t Ditched the 9-to-5 Yet

Jun 12, 2017 | 2 comments

The #1 Reason You Haven’t Ditched the 9-to-5 Yet

You cannot chip away at a business haphazardly and expect it to grow in the wee hours of the morning or late at night in those little slivers of precious time that you’ve managed to eke away. This is not how things work.

by | Jun 12, 2017 | 2 comments


It’s the end of the work day and you’ve dragged yourself home from a long, tiring day at the office. You had to get up at stupid o’clock to get ready for work and make sure the kids/dog/hamster were fed, watered and off to their respective places of care on time.

The work you do used to inspire you and you were stoked to get this job (you beat out 120 applicants with your charm and experience, boom!). Lately, it’s a chore. Your mind isn’t in it, your heart isn’t in it and all you can think about is your side hustle. The one that started out as a good idea but is now flopping on the verge of lifelessness, evidenced by to do lists, scraps of paper and open windows all over your desktop at home.

You’re stuck in a hard place. You want this new business to work so badly that it distracts you while you’re at your day job and looms over you when you get home, too tired to work more, and now you’re doing neither well. Every evening and every weekend is spent trying to catch up, but if we’re being honest here, there’s more Netflix and decompressing than working steadily into the night.

Sound familiar?

What a frustration!

How does anyone make the transition? We all need money to live and who the heck is financially independent enough to support themselves while they give their new gig the care and attention it needs to become successful? Unless you win the lottery, it seems unlikely that there is ever going to be an answer.

Do you know what’s got you stuck?

You don’t have a plan.

You cannot chip away at a business haphazardly and expect it to grow in the wee hours of the morning or late at night in those little slivers of precious time that you’ve managed to eke away. This is not how things work.

Building a business takes a lot of ongoing, consistent effort. But as long as you are focused and intentional about the work you are doing in those quiet bookends of the day, you can get there.

“I had zero clue what I was doing when I made the transition and would have appreciated guidance or a process from A-Z that helped me with the financial planning/security net. I also remember struggling with questions like ‘how do I know I’m ready to go full-time into freelancing?’ and ‘what kind of preparations should I make?’ and ‘how do I make time to build my business and make it self-sustaining when I’m still working a regular job?'”
Janine Duff,

The Four Pillars Plan

So what’s in a plan?

Essentially, you want to create yourself a very detailed, very focused plan in 12-week sprints that moves you toward a big goal. But first you need to envision what your business looks like when you are ready to transition. How much money will that take? What are the most important conditions that need to exist before you will feel comfortable leaving your job? What are you willing to compromise and what do you stand for?

Keep in mind that this will be different for everyone, as we all have different tolerances for risk, different motivations and, of course, different aspirations and visions for what success looks like. But if you stick to the following four pillars, you should be able to capture all of the necessary milestones that you want to achieve before you fly the office coop.

The first stage of planning a transition is to establish what your “turning point” is, or what conditions need to be present in order for you to move comfortably into full time self-employment.

To establish your Turning Point, ask yourself the following for each pillar…

What conditions need to exist in order for me to be ready to transition in this area? What do I need to have in place before I can leave my job? Who do I need to have agreement from in order to move comfortably into a new role?

Building a business takes a lot of ongoing, consistent effort.

Pillar One: Financial

Do a careful analysis of what you REALLY need in order to live. Also, build in some padding for unforeseen expenses, slow months, and investment in your business. Understand very clearly and realistically what your business will cost you in order to not only sustain it now, but grow to the volume you will need in order to meet your financial requirements.

Are there ways you can think differently about income? As in, could you flip your mindset to one where you plan for your business to be your focus and you maintain a small side job in the meantime to supplement your income? That’s a nice transition scenario and it might give you a shorter timeline to becoming free of a full time job.

Could you move to contracting or freelancing in your existing line of work ? That’s a great way to transition out as well, as you can typically build in a bit more flexibility to your schedule, and you can focus on moving to contracting for work that is similar to what you will do with your business.

Your financial analysis should also inspire you to think about how you are pricing what you sell. You want to find a way to create a mix so that you can appeal to many types of buyers – a small, quick sale as well as a more premium type of offer that would get you more quickly to your financial goal.

Pillar Two: Operational

What all needs to be in place for this company to operate as a full time business? Do you need systems in place? A bookkeeper? Have you structured the company properly?

Have you nailed down your processes for getting customers, processing sales, automating communications and your sales funnel (to take the pressure off some of your marketing activities), retaining and growing customers (farming is a lot more efficient than hunting!)?

Do you have enough time to do all the things? Would outsourcing get you closer to your desired end state? The investment in hiring help might actually relieve you of some of the things you need done that aren’t really your core skill set so have been sitting there, being unfinished.

Pillar Three: Personal Responsibilities

More than likely, there are elements of your personal life and responsibilities that are holding you back from transitioning to your full time role as a business owner. Sometimes these can be health issues, sometimes parenting schedules, volunteer obligations or even your relationship with your partner. If you are in a committed relationship with shared dependencies, it’s not only you that will be making a transition.

Do you need to focus on your health before you can take on more risk? Do you have family obligations
that need to be dealt with? Is your partner ready to support your transition?

Pillar Four: Your Job

Transitioning out of your current job is also a major consideration. Besides being a jerkface move, just upping and leaving with a few days’ notice won’t leave you or your employer in a good position, financially and otherwise.

It is important to make sure you have generated as much value as possible before you leave your position. Also, be aware of your contractual obligations for giving notice, and work backwards from that. It’s good practice to give your employer as much notice as possible before you leave so they have a chance to fill your position with the right person.

What do you need to to finish up at your job to make the transition with integrity? Do you want to finish projects, certifications, anything else? How much notice will be required when you leave?

The Milestones

Now that you understand the conditions that need to be true in order for you to be comfortable leaving your job for the world of business ownership, you must start to piece together a plan that will allow you to get to your Turning Point.

Looking at your conditions for transition, start to list off all the things that need to occur in order for you to achieve each condition. Some of these may be standalone, and some may be dependent on each other.

The Teeny, Tiny Steps

Alright, so you have some milestones established. But this is not enough in order to have a realistic, executable plan. If you were to stop here, you would probably never achieve these milestones because they are too big, and take too long, and are largely undefined.

Instead, we are going to talk about microplanning. Microplanning involves breaking your milestones down into teeny, tiny steps that can be completed in a manner of hours.


One more time, because it is so critically important – breaking your milestones into teeny, tiny, digestible tasks is the most important thing you will do to ensure you actually make progress.

If you cannot complete a task in a couple of hours, break it down even further. You want to list these under your milestones so you can ensure that each task contributes to the completion of a milestone, so you know that everything you are doing is moving you forward towards your goals.

Your Schedule

Commonly, business owners that are trying to grow a business while working a full time job have a very difficult time fitting new business activities into their schedules, because they are left with so little time at the end of the work day. This is why we broke down your tasks into such tiny, bite-sized pieces – so you can fit them in to the small periods you might have available. The reality is, though, that these availabile times will change and morph as you go.

That’s OK! As long as you commit to the process we establish here, and as long as you have created tasks that support your milestones, you can change as you go and as your schedule of available time changes.

The most important thing you need to get in the habit of doing is setting your daily schedule the night before. Write all your tasks down in a book, or in a task management application, and each evening, plan out your next day.

Putting Your Business On Cruise Control

One of the most amazing things about the business technologies available to us today is that we can put part of our business on autopilot by investing a bit of time to set up systems and build some content.

If you are already strapped for time, think about how you can create content distribution scheduling so that your posts, newsletters, articles and social content can continue to be distributed, even if you are not there to do so.

This automated distribution ensures you remain visible and, as mentioned earlier, your brand continues to become more familiar and, therefore, trusted amongst your customer groups.

While you’re at work, your business can keep growing.

Your Promise

Now that you’ve built the foundation for your transition to a wildly successful, happily satiated entrepreneur, you need to do one more thing.

Make a promise to yourself that you will remain dedicated to your plan, and that you will, for yourself and those around you, do everything in your power to be kind to yourself and compassionate, and that you will embrace each challenge as a new problem to be solved en route.

Tell me in the comments…

What are some of the things holding you back from leaving your job?


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  1. Janine

    LOVE how you broke a plan down into 4 pillars. I’ve never thought of it that way, but it gives me an actual structure to work within. Thanks for the mention, too! 😉 I wish I had access to this info WAAAY before I made the leap to full-time freelancing.

    • Stephanie Hayes

      Oh thanks! So glad you found it useful. I was inspired by your comments and can’t wait to launch the full transition program offer. A plan makes such a difference to confidence, stress levels and self doubt!


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