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You’ve decided you want to take the leap and leave your 9-5 to build a creative business. That’s exciting news! But before you hand in that letter of resignation, there are a few things you should do to help make the transition from employee to entrepreneur a little easier and give yourself the support you need–financially, mentally, and emotionally. 

First things first, you need a plan. It seems obvious but you’d be surprised at how many people overlook building this crucial step. A plan outlines what you need to do and also provides you with a sense of direction. Speaking from experience, I know how stressful it is to walk away from what is thought of as a “safe” job, especially when you’re taking a step into the unknown. By building a plan that addresses the elements below, you’re making the transition a little less unknown while simultaneously building confidence in your decision to make this change.


The first thing you want to do is figure out your burn rate, or how much money you need to make in order to meet your expenses. 

For the sake of this example, sample numbers for the equation are listed in brackets:

  • Figure out what you spend each month on essential bills such as rent or mortgage, utilities, groceries, insurance, etc.

= _______________________ ($3000 per month for bills)

  • Next, factor in how much you spend per month on self-care like going to the movies or out for dinner, and other items like a membership to your gym or getting your hair cut.

= _______________________  (Average $250 per month on self-care)

  • Determine how many months of bills you want to be saved before you leave your 9-5.

= _________________________  (Approximately 6 months)

  • How much can you save per month after paying your bills and cutting back where possible?

= _________________________ ($2,000 per month)

Here’s where the math comes in. To give you a ballpark or idea of timing, take the total amount you want to be saved per month ($3,000 in bills + $250 in self-care) and multiply it by the number of months you want to be saved. Next, divide this number by the total amount you can save each month:

  • $3,250 in bill payments needs to be saved each month x 6 months = $19,500 $19,500 divided by $2000 average savings per month = 9.75 months

This means in about 10 months you’ll feel ready to take the leap. 

But it’s important to mention that you don’t want to wait ten months before you start. You want to start putting savings aside now. By intentionally building your savings, you are creating a financial cushion for when you make the break and leave your 9-5, but you’re also creating forward momentum toward your desired goal. Taking the initial step and putting money aside for post 9-5 acts as a natural kick-starter to other pieces of your exit strategy. This is the first step to reclaiming control over your career trajectory.

At this stage, I also recommend that you work with a financial advisor to understand any implications and make sure you have enough to cover your living expenses and a little self-care. The simple math I just outlined is a great start and can give you a basic idea of what you need and how you can get there, but when you bring a financial advisor onto your transition team, they’ll have insight and knowledge that you most likely do not have that can help you reach your goals faster and more efficiently. Many banks and credit unions offer financial services for their clients, so if you don’t currently have a financial advisor, I’d recommend getting in touch with where you do your banking and start a conversation with one of their advisors.


In addition to building your savings, another way to contribute to your finances during the transition is to find a bridge job that will provide consistent income while you’re building your creative business. It may seem counterintuitive to leave your current job for another job, but the rationale behind a bridge job is that it allows you to leave your 9-5 a little earlier and still collect a regular income. 

Maybe you’re struggling at work and it’s starting to impact your mental health and your life outside of the office. Or maybe you want to have fewer hours of the day focused on your job and more time to focus on building your business. Whatever the reason, a bridge job is a great way to keep making money while you create your new business venture. It may be the solution for those of you who are feeling like you need to get out sooner rather than later. 

A bridge job can also greatly reduce your stress level because you’ll typically have less responsibility than in your current role, allowing you to regain some time and energy for other things. The key here is lowering the level of stress and responsibility associated with your role. It’s highly unlikely–and in fact, I would never recommend–that you transition from one role into another of the same or higher level of oversight. That’s not a bridge job. That’s a career change. And a career change is not what we are going for as we transition you from employee to creative entrepreneur.


  • Why is it important to you?
  • Why do you want to own a business? 
  • What do you think being a business owner will do for you and your lifestyle and why do you want this change?

Your finances are lined up and you have a plan in place for how you’ll fund your burn rate. Now it’s time to get into your business idea. Knowing what you are doing is key. And I don’t mean that in a generic or basic approach. I mean really digging into what your idea is and why you want to do it. 

Getting up close and personal with what motivates you will help you face difficult decisions as you make the transition. It will also help you maintain your focus when shiny object syndrome starts to rear its magnetically distracting head. 

Why you do anything is important. Dig into this. Make a list, write it down and reflect on it. 

Keep your list somewhere visible so that you can refer to it easily. This list is meant to be a visual reminder of what you are striving for and why it matters to you because there will be times when you feel discouraged and doubtful. Include things that keep you on task, motivated, inspired and accountable. Build it when you are excited about your new venture because it’s creating an external record of your mental image during a time of optimism, opportunity, and desire for change. The end goal here is to create something tangible that reminds you of the vision and goal you have for yourself, and more specifically, that your goals are worth working for.


Your values are important. You’re looking to leave a situation that doesn’t align with you for whatever reason. As an entrepreneur, you have the opportunity to build something for yourself that does. Get crystal clear on what matters to you so that you can build a life and a career that reflects this. 

Find a values assessment. I have one that I designed specifically for my clients but there are several free ones available online as well. Find one and take it.

I’m going to take an educated guess and suggest that part of the reason you are experiencing a disconnect with your 9-5 is that there is a disconnect with your values. What you are doing every day isn’t in alignment with what you value. And when your values aren’t being honoured, or worse, when your values are being directly challenged or disrespected, your response is to become irritated, annoyed, angry, frustrated… I think you get the drift. You have the opportunity to build a business that honours your values. Grab hold with both hands and don’t let go.


Everything you’ve done to this point is fantastic. You’ve put some things in place to build confidence and outline what you want to create for yourself. But without building your mental and emotional readiness, you’re putting yourself and your energy at risk. 

Being an employee and being an entrepreneur are two very different things and it’s really tough to run a business with an employee mindset.  In fact, in my opinion, it’s more than tough. I don’t think it’s feasible.  

In my experience, approaching your new business as an employee creates two scenarios: 

  • You panic work in a constant state of chaos because you’re not sure what needs to be done and by when, or;
  • You gradually get around to your office after you’ve filled most of your day with wordles and crosswords because you’re not sure what needs to be done by when.  

Make an effort to prepare yourself mentally and emotionally for the switch so you don’t swing to the far ends of the pendulum. Obviously, neither scenario is optimal when you’re trying to build a profitable business and both situations directly impact your mindset, and more specifically, the confidence you have to actually pull this off.

Consider choosing your ‘last day’ date for your 9-5 and put it on your calendar. Next, start building a workday schedule focused on getting you to that goal. Structure your time with blocks of work that help you make progress in building your business while you take steps toward your chosen date. 

Setting a deadline helps you get ahead of the procrastination cycle. 

When it comes to what you need to do in order to meet your deadline, do some research, network with people who are where you want to be and ask a lot of questions. Build your community and set aside time to meet people who inspire you and to whom you aspire. I’m sure you’ve heard the saying that you are the average of the five people you spend most of your time with, so spend time with people that you want to be like. Bring up your average and find your people so you can strengthen your mindset. Build your mental and emotional readiness.

It’s not easy to stand up and push back on everything you’ve been taught you ‘need’ to do in order to be able to support yourself. 

It’s not easy to invest in yourself and truly believe you’ve got what it takes.

And it’s not easy to walk away from a ‘safe’ job to follow an unknown path that attracts the judgement of others. 

It’s not easy, but neither is remaining in a situation that you don’t want to be in.

Build a plan that supports you financially. 

Get really clear on what you want and why. 

Find people who fuel an empowering mindset and champion your mental and emotional readiness to get after the change you desire. 

And for the love of all things, stop taking advice from people who have never been where you’re going

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