Workland Blog Post

Making the leap from Corporate to Start-up entrepreneur


Questions you need to ask yourself before leaving your job

by Julie Hubert, President & CEO of Workland

At some point in their careers, many people will ask themselves THE question: Corporate or Entrepreneurship? If you have recurring thoughts of being your own boss, avoid any regrets down the road and at least seriously consider and evaluate the possibility of making the big shift. If you are made to be an entrepreneur, not following your instincts will inevitably follow you throughout your career. The contradictions you will live in the traditional Corporate job model will have you too often feeling like a round peg in a square hole, slowly eating away at your job satisfaction and overall work-happiness. Many have successfully completed the shift from Corporate to Start-up entrepreneur and found that the benefits on the other side of the fence are numerous and extremely rewarding. However, there are some very important questions to ask yourself before taking the plunge that is sure to have you feeling like Alice in Wonderland.

Points to consider before leaving your Corporate job:

Are you willing to pay the price of Freedom? A Corporate job is a lot like being a horse in a stable. Some stables are better than others but in general it’s a pretty comfortable formula. Horses are trained to perform and give results within a discipline for which they show great potential. They have good shelter provided, feel safe and secured, are well fed, admired and have a good idea of what’s ahead of them. In exchange, they must respect and follow the rules of their owners and do what they have been trained to do, or risking having to find another stable. On the other hand, becoming an entrepreneur after having been in Corporate can be compared to a horse being set free into the wild after spending many years in the comfort of a stable. The horse is free to go as he wishes, no saddles, no bridles, no whips or rules but…no food. Predators everywhere. No shelter. No security. No fancy accessories. It’s definitely a shocker in the beginning. But the horse must and will learn to adapt in this new environment where he now benefits from being able to do as he wishes, run and play on his own agenda, create his future and reap the benefits. However, the price of freedom is that he must fend for himself constantly and be stressed as hell as he continually faces dangers and the unknown, especially in the beginning as everything is new. Is your need for Freedom more important than your need for Security?

Could you live without the great Corporate perks? In Corporate we seem to forget how great some of the benefits are, that is until we lose them. Nice offices, luxurious furniture, laptops and cell phones, higher cube walls as you move up the ladder, or if you are lucky, your very own office. Beautiful conference rooms with nice views, expense reports, nice restaurants, assistants, vacations, fancy conferences; all things you will fully or partially need to give up for some time. Jumping from Corporate to being on your own is much like going back to live in a small 1-bedroom apartment after having lived in a beautiful Westmount home. You’ll most likely start working from home in your university jogging pants or jeans and once you progress enough, shared offices is the next big upgrade. For a few years your offices will be small, modest and simple and IKEA will be your new go-to place. In exchange for what? For the opportunity to go get bigger and better perks without having to wait 20 years for them and the shot at becoming a “perk creator” for the people who will work for you. Could you trade in your fancy suit for your joggings or jeans in exchange for the express-route to that large corner office with view?

Can you live without structure? If you are an entrepreneur at heart, you probably often get frustrated with heavy structures and processes. Established companies have time-tested procedures that create direction, security and which limit the impact of errors. As an entrepreneur, nothing is structured and there are no processes, rules or pre-set objective and strategies. You’re the boss now! Finally, you are able to do things your way and implement your ideas without anyone breathing down your neck and being able to over-ride you. But since guidelines and supporting departments and services are inexistent, you’ll often be flying blind with no one to tell you the correct answer. Now that you are in charge of ALL aspects of the business instead of your functional specialty, you’ll be sure to make mistakes along the way, something kind of hard to accept for A-players… And A-players are often the ones who start businesses. However, as you test, experiment, iterate and learn through your successes and errors, you will very quickly acquire the equivalent of a hands-on MBA and the equivalent of 10+ years of experience. Can you navigate sanely without structure, outside of your field of expertise, in exchange for CEO-level training experience?

Can you live without your pay-check? Obviously the biggest risk associated with leaving your Corporate job to become an entrepreneur is the financial one. By deciding to go off on your own you’ll need to say goodbye not only to some of that hard earned money you set aside but also to your pay check. Even the simple thought of not having that steady flow of income is often the one and only thing that keeps people in jobs they hate. Letting go of that constant stream of income is probably what will hurt the most and create high levels of uncertainty, depending on your situation. You will bet your career (aka: pay-check), your reputation, probably some or all your investments and if you don’t succeed, you may be stuck with debt that you will need to pay back over a few years. Big risks = big potential paybacks but how far financially are you willing or are you able to go to follow your dream? Unless you are already well off financially, if you make the jump you’ll need to make some radical financial adjustments in your life. Can you say goodbye to your daily Starbucks latte for a while for the possibility of one day being able to earn in one month what would currently take you 10 years?

Can you handle (lots and lots of) pressure? : There is a great deal of pressure in Corporate, especially depending on your job, but when you are the leader of a Start-up, suddenly the heat is up 1000%. When you think you’ve seen it all, a bigger challenge comes out, a bigger deception that throws you off your feet or a seemingly impossible problem to resolve that has you up all night. As part of a department in Corporate, there is pressure, however, it is scattered over a team of people and further diluted through the organization. In a Start-up, even the new intern can feel the heat so imagine if you are leading it. As an entrepreneur, it’s also no longer only about yourself but also about the crazy people that followed you in your mission. What’s the ROI on all this pressure? Pressure means that you are in charge and if you are a real entrepreneur at heart, its what you have been missing all throughout your career in Corporate. Pressure is coming at you because of the challenges associate with accomplishing something great, something big, something which can have major impact in a field, in an industry and maybe even in the world…? Can you handle being responsible for people’s futures in exchange for the opportunity to become a world-class leader?

Are you ready to work 24/7? In most Corporate jobs, there is a schedule to be respected, people work hard, go home, may work a little overtime but they are entitled to “unplug” and have a life outside of work. As an entrepreneur, forget about having a normal life for a few years. The line between or holidays, vacations, week-ends and evenings will often be blurred and even if your not working, some part of your brain will be hard at work trying to resolve an issue related to your business. Actually, if you don’t watch yourself carefully, your health can take a serious beating. What do you get in return? Well at minimum, the word boredom will never be part of your vocabulary again that’s for sure. However, the real return is that it won’t ever feel like “work”. Because you are in a role that fits your profile and personality, because you are chasing a dream that you are passionate about, you’ll never “work” another day in your life. Are you ready to work hard like never before in exchange for the opportunity to never have to “work” again?

Starting and leading a business is hard. It’s not made for everyone and no books or articles can really prepare you for what’s ahead. But if you are made to be your own boss and are willing to make the necessary sacrifices, you will have the time of your life and never look back and regret your decision. In exchange for some incredible “lows” you will feel unbelievable “highs” and feel alive day after day surrounded by inspiring like-minded people who share your passion for a common mission. If you know you have what it takes and you’ve found a project you are passionate about, by all means GO FOR IT! As bad as it can look from the outside, there are always solutions to the seemingly impossible hurdles that lie between you and your entrepreneurial dream. As you make your decision of whether or not to leave the comfort of your current stable, remember that what you will need to give up is no match for all the gifts, growth and incredible experience you will live in return for having been brave enough to make the jump.

Still unsure about leaving your job?

You have the entrepreneurial personality that makes you unhappy in Corporate yet you are not sure to want to face the tougher sides and risks of starting a business? Or you just haven’t found THE idea that will inspire you to give it all up and take the big leap? Why not work in a Start-up?! Your entrepreneurial side will definitely be more at peace and you can enjoy many of the perks while avoiding the major downsides of a full jump. You will definitely learn and grow at rates you could never think possible, have opportunities that would take you 10+ years to get in Corporate and acquire a certain level of entrepreneurial experience before deciding to jump. Working in a Start-up is probably the best place to live a more comfortable middle point between both worlds and their extremes, and you’ll have front row seats and actively contribute to one of the world’s most incredible and rewarding journeys.


About me: My company Workland has developed an intelligent talent acquisition platform that automates job search & recruitment.  Compatibility between parties is calculated to pre-qualify relationships and evaluate potential fit right from the start. Welcome to the future of recruitment!   

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