When & Why to Leave Your 9-5

2020 was the year I burnt out in my 9-5 and had hit the lowest point in my life.
2021 I made the decision to leave the corporate world and pursue entrepreneurship as a leadership & mindset coach and haven’t looked back since.

The topic of quitting your 9-5 to pursue other dreams is still on an uproar even 3 years after the initial wave that has been caused by Covid, Us being stuck and bored at home and seeking new ways of generating income.

However, this is not a decision that should be taken lightly, and I want to go into some points as to when and why you should quit your 9-5, and I’m going to be straight with you, you might actually think staying at your current role is what you will walk away with after we have covered everything - and that from the mouth of an obviously biased entrepreneur.

The reason why I’m saying this is because very often people have a specific expectation of what it means to be self-employed as well as what their success should look like. If I ask clients of mine who are considering leaving their 9-5, a common answer is to make a shit tonne of money, work 4 hours a week and travel the world. Whilst this may initially do sound like a dream, when we start to dig deeper into this version of their most successful dream life, chances are they actually don’t want any of that.

And there are two problems with this. First up, when you leave the 9-5 and start your business because you want more time freedom, you might actually find yourself working MORE than before because now everything is on your shoulders. I wrote a post on LinkedIn the other day saying that every entrepreneur can add countless new roles to their CV like Content Creator, Video Editor, marketing Strategist, CFO, Head of Operations, Customer Service, Copy Writer, Website Designer, Podcast host and so many more NEXT to their actually title they introduce themselves with, like in my case Leadership and Mindset Coach. Entrepreneurship takes time and effort, anyone who has achieved the financial abundance, time freedom and location flexibility most likely has been putting both of that in big times before enjoying the fruit of their labour.

The second problem goes even deeper into the personal level though. Because it is tightly attached to what success really means to you. Do you actually want to travel the world or do you rather stay close to your friends and family? Do you actually enjoy having loads of freetime or do you love working on things that spark joy in you? Do you really want to make millions or are you actually already satisfied with making for example 5-10K a month to cover all the bills comfortably?

For example, Michelle Obama’s version of success is: “Success isn’t about how much money you make. It’s about the difference you make in people’s lives”

Or Meryl Streep said: “The formula of happiness and success is just, being actually yourself, in the most vivid possible way you can.”

To figure that out, you got to get clear on what your personal definition of success is, completely detached from what you might think success SHOULD look like based on the fancy cars, beach houses and awards that other people have won.

So ask yourself:

What is your true definition of success?

What does a day in the life look like, when everything is a 10 out of 10?

Maybe it’s actually to have a positive impact on one other person, to enable a comfortable life for your kids, to just love your job and being able to spend time with your family. Or maybe it is making more money, getting that promotion, living in a penthouse in Dubai.

With this information, you can then think about where you are right now, and what’s the gap.

If you are currently working in a 9-5 is your version of success possible or would be quitting or entrepreneurship the way to get there?

And you got to be real honest with yourself here.

For me, I thought for a long time that I will forever stay at my company until I make it as a CFO. However, I ignored and neglected my inner calling to do my own thing during those years. My first ever childhood dream of my work life was to be a boss. I translated that into CFO for almost a decade, until I couldn’t stand any longer working for someone else, not having the impact I sought to have and not being able to create my own schedule and decide my own workload based on my passions and strengths. This all influenced my version of success in which I have the freedom to do what I want to make this world a better place. My version of success is based on positive impact on others whilst also allowing myself to live freely as who I am. Anything else is a great byproduct, like location flexibility or financial freedom. I know, that I already have been very successful in my life as I have changed countless other peoples lives for the better, and I did it my way. Which is my mantra.

So I wanna ask you, with this new definition of success, is leaving the 9-5 your way?

In addition, it is rather vital asking yourself whether it is actually a smart thing to do at this point in time for you. The last thing we would want is for you to hand in your resignation, run off, and then find yourself struggling.

So some aspects that are important to get clear on are your financials, support systems, and Plan of action.

Financials are crucial, especially if you want to create more financial stability and freedom in your life, it might not yet be wise to leave the secure income stream. Many entrepreneurs start with side hustles next to their full-time roles or go part-time until their business is profitable enough to sustain their lives. For me personally, I had the advantage of a redundancy package that supported me in the first years of business as well as additional backup from my boyfriend who supports us with his 9-5 income for the times when the business does not generate enough income. Because there will be dips and months with low numbers, and you got to be prepared for those times.

The second aspect I mentioned was the support system, like partners, friends or family, mentors and coaches that will have your back when things get tough not necessarily financially but more emotionally. Because as you go through this time you will face mindset blocks, limiting behaviour patterns, changes in your surroundings, and more that require a safe space for you to work through. For example, many of my clients struggle with Imposter Syndrome and Self-doubt whether they are really cut out to be an entrepreneur. So together we not only work through those moments to get out the other side, but we also build a growth mindset, hone their leadership skills, beat procrastination in the butt and create a work-life balance that is sustainable rather than draining. I even had a set of different coaches I was working with and also joined a mastermind so I could be surrounded by like minded women who were going through the same, honestly building new connections and having my coaches was and still is key to creating my business.

The last aspect is the plan of action. Instead of diving into all of this blindly, create a plan of action with what you want to do and how you want to do it. Or in other words, your strategy and execution plan. This way, you feel prepared for when you are all of a sudden on your own with 24 hours a day and all the possible tasks that you can tackle. Putting up a clear red thread can help you to feel less overwhelmed and gain momentum. Again, this is something that I often work with my clients on so they don’t feel like winging it every day. For example, my plan was to finish my certification, get my coaching hours in and then get accredited whilst building my platforms and showing up daily to sell my services.

These 3 aspects will help you tremendously in navigating the transition from your 9-5 into entrepreneurship.

To sum it up, and to answer the question as to when and why to leave your 9-5, get first crystal clear on what success looks like for you and whether entrepreneurship is your way to get there. Then also make sure your financials are in order, that you have a strong support system, and a plan of action.


Are you currently facing a change in career or wonder whether to take the leap into entrepreneurship? Let’s work together so you can find your path that feels most aligned to you, brings you joy and fits YOUR version of success!

Josi Dumont

Leadership & Mindset Coach, Author, Podcast Host

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