3 Tips To Help Prepare You To Leave Your 9-5


I am Jess! Ottawa brand strategist and website designer helping ambitious service-based businesses grow with confidence through meaningful design. I'm the type of gal that use one too many exclamation mark in my emails and can only have one cup of coffee a day. Weird, I know. If you ever want to chat any thing biz, branding, or well - life, feel free to reach out!










It’s officially been two years since I first made the transition to leave my 9-5 job to pursue running my business full-time!

Truthfully, I will probably never get tired of saying that and celebrating that, because it’s such a huge accomplishment, as anyone who’s made that transition knows! Fully investing in the transition requires so much trust and faith in yourself, and bravery to take the risk to start your own business in the first place – so taking that on is something to be proud of! 

For those who know me, self-trust & identity are two things that I struggle with the most. I tend to seek external validation to help make informed decisions. So leaving my 9-5 was one hell of a test from the universe to help me break out of that pattern, but I am so grateful that I went through and learned in this transition period. 

It’s easy now that I’m on the other side of the transition from a 9-5 to an entrepreneurial business to say how grateful I am that I did, but when I look back at that time, I wish I’d had a guide to tell me how to prepare for the transition itself. 

So, in the hopes that I’ll be able to inspire you to finally jump off that cliff and begin your transition from full-time to starting your own business, I’m sharing my top 3 tips that will help you prepare for the beautiful, wild, and risky journey ahead! 

And while this blog post is to help prepare you to leave your 9-5, you may find some nuggets of wisdom relevant to anyone making a big life decision! 

Tip #1: Identify Your Worst Case Scenarios

When you’re about to take the risk of starting your own business and leave your 9-5 job, it’s so easy to fall into the pattern of looping on your big, looming fears. 

We all have them, and being scared or unsure in this process is normal – I went through this a lot! 

And though that fear is a natural protection mechanism we have that we tend to try to ignore, we can use fear to our advantage – by getting to the nitty gritty of EXACTLY what you’re scared of. 

By identifying your exact worries and concerns, that big, looming feeling of control these worries have on you will suddenly feel a lot less scary, more concrete, and more manageable to face because you’ve outed them from their aren’t non-descript forms into something more solid. 

👉🏼 Once you’ve identified your worst-case scenarios, you then can strategize and plan what to do next to avoid these scenarios or create a plan of action to support you if they do.

By shifting from our natural protection and survival mode to problem-solving mode can help make those worst-case scenarios less intimidating and more of a simple problem that needs a solution. And we know that entrepreneurs are the problem-solvers of the world, so this process won’t be as difficult as you think!

Ultimately, becoming friends with your worst-case scenarios is the best way to create a plan of action to execute to prevent them from happening, or feeling safe and supported if they do. In doing this hard work now, your future self will thank you! 

Tip #2: Act As An Investor In Your Own Business

A lot of people wonder how exactly I built a six-figure business so quickly after leaving my 9-5 because truly, there are still some days where I don’t believe it either! But really, my answer to that question: you need to invest in yourself and your business while working your 9-5.

Now, I know the whole point of this post is to help you leave your 9-5 because you aren’t completely happy there anymore. However, by being solely focused on the process of leaving, you’re missing out on the one silver lining of your full-time job: your bi-weekly paycheque! 

That paycheque is your secret weapon when it comes to starting up that new business. 

By putting away a (small) portion of that money into a savings account and using those savings to invest in your business, you are giving yourself a leg up to get to a safe and stable place you’ll want to be before you fully leave that 9-5. 

For me personally, in the first year of my business, I invested around $10,000+ from my full-time job into my business (which I don’t take lightly and appreciate how fortunate I was). I used these financial resources in various ways, including:  

  • Working with business coaches and outsourcing help
  • Investing in courses and masterminds that helped perfect my craft
  • Investing in systems/platforms to streamline the backend of my business.

How you use these resources is ultimately completely up to you, but the important takeaway here is to invest in yourself, your education, and your resources as a business owner to give your business the best chance at success. You deserve it! 

(That goes without saying that bootstrapping can also be equally successful! It truly depends on your situation and lifestyle. In my first business, I bootstrapped and maybe spent $500 to get myself set-up. This time around, I wanted to expedite my growth!)

If you don’t know where to get started in terms of investments or would like some resources to know what’s out there, here’s a blog post on How to Invest in Yourself as a Business Owner to get you started on the right foot. 

Tip #3: Find Evidence of You Overcoming Failure

We’ve all failed before, plain and simple. Of course, failing never feels good, but it’s what happens afterward and how we overcome those feelings of shame from failing that dictates our resiliency.

As a business owner, I can tell you that failure is sometimes bound to happen. And that’s okay! Failing is all part of the process. 

This is where shifting our mindset is key. 

Failure can be one of those big looming fears we were talking about in tip #1. But realistically, most of the time when we do fail, we learn something that helps us in the future to create an even stronger foundation moving forward. When we shift our fear of failure to embracing that failure as a stepping stone to success, the road ahead that once may have felt bumpy can feel a lot smoother with less resistance. 

To put it simply, there is no failure, failure is just lessons learned. 

And while knowing this is helpful, another way to reinforce your resiliency and belief in yourself is by finding the evidence of when you’ve overcome failure or setbacks in the past, and recognizing your strength! 

Once again, our brains are wired to protect us. So what we need to do is find evidence of us overcoming failure and accepting failure as part of the process to disarm that protective part, and let ourselves move forward with confidence. 

Ultimately, finding reassurance in the times you’ve overcome failure will help prepare you to leave your 9-5 so you can accept the potential that something might not work out, but in the end everything will be okay. We can pick ourselves back up and move on to bigger and better things, just as we’ve done before! 

Remember that at the end of the day, rejection can always be seen as redirection. This little phrase, along with finding evidence of overcoming failure, were the two main mindset shifts that helped me leap into entrepreneurship from a 9-5. 

I sincerely hope that these tips helped you feel more confident and supported in your decision to make this big leap. The journey ahead won’t be easy, but hopefully, with these tips, you feel a bit more prepared and reassured in yourself. 

Know that the fact that you’re even considering making this transition is something to be so proud of, and means you are incredibly brave. Carry that with you on your journey ahead! 

If you ever need some extra guidance or advice on how to get started in this transition, I offer 1-hour consultations where we can chat all about it! Just send me a DM on Instagram, and we’ll set something up! All I ask in return for my time is a small donation to my favorite non-profit to help fund a learning center they are building in Mozambique for young girls. 

 I always love chatting and making new connections in the industry, so don’t be shy to reach out. 

And remember….

You’ve got this!!!


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