5 Steps To Take Before Making The Leap From The Corporate World To Entrepreneur

Deciding to leave your job to work for yourself can result from a significant life change. Other times, it is simply a matter of finally being ready to jump after months or maybe years of debating it. There may never be a clearly defined “right time”, and there will always be unknowns on the other side, but there are ways to prepare and ensure that you are set up for success. If you’ve been considering leaving your job to wholeheartedly pursue your side hustle or passion project, read my five steps below to help you start moving in that direction!


Daydreaming about the ins and outs of starting your own company is great, but it’s important to consider the motivations behind your vision. Are you starting a company that is filling a gap in the market and that you yourself would utilize? Are you creating a business that gives back to a larger cause? Or perhaps you want to freelance full-time because flexibility and work life balance are priorities for you. Write down why you are passionate about working for yourself and marinate on it for a while because this is what you will come back to time and time again when things get tough — because trust me, it will be a LOT of work! Make a list of the pros and cons for leaving your current position and then consider what is most important to you. Perhaps a con is working by yourself from home, but maybe that isn’t so bad when listed next to a pro of getting to work with clients who inspire you.  


Before diving into your project with both feet, launch your venture as a side hustle and pursue it part-time outside of work hours. Create a business plan, map out your short term and long term goals, and start building your company. This will give you a better understanding of financial expectations and also confirm if this is really and truly what you want to do! If you do decide to make the leap, you’ll already have a solid foundation in place.  


The decision to leave your job is ultimately up to you, but you don’t have to make the decision alone. In fact, I would highly recommend consulting someone, or multiple people, who you trust as mentors and advisors. This is a big decision, and you want to be sure that this path is right for you and that your business idea is supportive of your strengths and skill sets. A couple of side notes to go along with this point: first, we know that the ability to up and leave a secure job is not an option that is available to everyone, and we are very grateful to have had the opportunity. Secondly, if you are considering making this transition but are fearful of the unknowns, it’s important to remember that it doesn’t have to be a forever decision. As with accepting any new job, you aren’t committed to it forever, and if it’s not the right fit you can pursue something else. Adopting this perspective will help alleviate some of the anxiety and pressure you might be experiencing.


Working for yourself can seem daunting and isolating. How do you grow and learn if you don’t have a manager or driven coworkers? How do you always make the right decisions for your business without being able to consult others? The thing is, working for yourself doesn’t mean you have to rely on your own intuition for every decision. Build a network of people in a similar field by offering to treat them to coffee in exchange for their advice. Use LinkedIn and social channels as tools for reaching out to people you have never met (yes, I have done this and have received successful responses!). Establishing a support system of talented, ambitious people willing to offer guidance is invaluable for the success of your company. And it also makes the process a lot more enjoyable when you have a network of inspiring individuals to bounce ideas off of!


If your side project isn’t lucrative yet, it’s of course a financial risk to put all of your eggs in one basket and say goodbye to a regular paycheck. While you’re gearing up to take the leap, be sure that you are saving up a rainy day fund that will help keep you afloat as you work your way towards a steady income. Financial experts suggest a three-to-six month cushion of living expenses, and you may want to adjust that amount based on how much you will be relying on savings when you start your venture.

Are you considering taking the leap to start your own company or join the freelance world? I’d love to hear your thoughts on how to prepare and what your biggest concerns are. Or maybe you have already done it, we would love to hear what worked for you!

Looking to leave your 9 to 5?

Here’s the thing. You can either burn yourself out working your 9-5, your side hustle and raising your family, OR you can launch an online business that changes more lives and puts more money in your pocket. PERIOD.