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A few years ago, I was an employee. It feels like it was ages ago, but in reality, it hasn’t been that long. I think it feels longer than it has been because there has been a lot of change in that short time which distorts my perception of the passing of time. 

When I left, I was a member of a Senior Leadership Team where I worked closely with a team of five other senior leaders and the board of directors. I had a close and respected working relationship with my CEO and feel fortunate to have been able to learn as much from him as I did. I was also blessed to work at a company where I forged friendships with my colleagues over the 8 years I was there–many of whom I still keep in touch with today. 

From the outside looking in, everything was great. 

But from where I was sitting, I was desperate for change. 

It wasn’t the organization. It was me. I wasn’t where I wanted to be. In fact, I was far from it. The irony here was that I worked very hard to get to where I was. I thought it would feel like it was where I wanted to be, but once I got there, I realized how wrong I was. 

I know this experience isn’t exclusive to me, especially for people who find themselves in an industry or field so foreign from what they imagined for themselves at the beginning of their careers. 

Fast forward to today and I’m building a pretty great business for myself and helping other creative women do the same. I know what it’s like to be longing for something different. Something that lets you be who you want to be. But I also recognize the financial constraints and feeling the need to stay at your 9-5 because of bills, life, and just not yet being ready to make the break. That’s why I’ve put together a few things you can do before you quit your day job that can help pave the way to becoming a creative entrepreneur.


It seems obvious but you’d be surprised at how many people overlook building a plan. A plan outlines what you need to do and also provides you with a sense of direction. It builds confidence in your decision to leave your 9-5 job. It’s nerve-wracking 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, you’re making the transition a little less unknown. 


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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. 

Let’s do some simple math:

  1. Figure out what you spend each month on essential bills such as rent or mortgage, utilities, groceries, insurance, etc. = _______________________  For this example, let’s say it’s $4000
  2. 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. = _______________________  Again, for this example, we’ll use $500 per month on self-care
  3. How many months of bills do you want to be saved up before you leave your 9-5? = _________________________ We’ll say 6 months for the sake of this example
  4. How much can you save per month after paying your bills and cutting back where possible? = _________________________   Let’s estimate around $3,000 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 ($4,000 in bills + $500 in self-care) and multiply it by the number of months you want to have saved. Next, divide this number by the total amount you can save each month.

From our example you need $4500 in bill payments to be saved each month x 6 months = $27,000 divided by $3000 average savings per month = 9

This means in 9 months you’ll feel ready to take the leap. 

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

I also recommend that you work with a financial advisor at this stage 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 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 starting 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 corporate gig for another job, but the rationale behind a bridge job is that it gives you the ability to leave your 9-5 a little earlier and still make regular paycheque. 

A bridge job may just be the answer for those of you who are feeling like you need to get out sooner rather than later. 

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 give you continued income while you create your new business venture.

A bridge job can also greatly reduce your stress level because you typically have less responsibility than your current role, allowing you to regain some time and energy for other things. It’s highly unlikely–and in fact, I would never recommend–that you would transition from an executive or managerial 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 corporate employee to creative entrepreneur.


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. 

  • 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?

Getting up close and personal with your ‘why’ will help when you face difficult decisions as you make the transition, and 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. 

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Keep it somewhere where you can refer to it easily. This list is meant to remind you of why you are doing what you are doing to help keep you on task, motivated, inspired and accountable. Building it when you are excited about your new venture is the perfect time because it creates an external record of your mental image during a time of optimism, opportunity, and desire for change. 

There will be times when you’ll wonder why you’re doing this and question yourself. This document will ground you and serve as a tangible reflection of your dream goal. It’s something you can hold in your hands and look at when you start to feel discouraged to serve as a reminder that what you are doing matters and that you have a vision for yourself that is worth fighting for.  


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Related to your why, but more specific to who you are rather than what you are doing are your values. Your values come into play here because you want to 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 online as well. Find one and take it.

Figure out your own personal values but also put yourself into the role of a budding entrepreneur and spend some time crafting values for your creative business. Your personal and business values don’t have to be identical, and in fact, they likely won’t be. However, you do want them to be complementary. 

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. Take it!


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Everything you’ve done to this point is fantastic. You’ve put some things in place to build your confidence and really outline what it is you want to create for yourself. But without the proper mindset, you’re going to hit roadblock after roadblock as you travel down this new path. 

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 tasks 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 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.

At this stage, I suggest identifying the date you will leave your 9-5 and 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 and see you taking steps towards your chosen date. 

When it comes to what you need to do in order to meet your deadline, I recommend you do some research, network, and ask a lot of questions. Build your community and set aside time to meet people who inspire you and who you aspire to. I’m sure you’ve heard the saying that you are the average of the five people you spend 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. 

Doing this gets you ahead of the procrastination cycle because you’ve set a deadline.

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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 to ‘make it.’ 

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

Find your people and strengthen your mindset. 

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

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