Climbing The Ladder

6 Things You Need To Know Before You Quit Your Day Job

By | Tuesday, June 02, 2015


It took me a long time to build up the courage to quit my day job in pursuit of something I loved. Before I came on board full-time here at The Financial Diet, I juggled a 9-to-5 job and moonlighted (and weekend-ed) on all things TFD. The extended period of time during which I had “one foot in, and one foot out” so to speak, was due to a combination of waiting for certain things to line up, getting my finances in good standing, paying off some debt, and getting myself mentally prepared to make a big change. Sometimes, stepping outside of your comfort zone is more difficult than you would like to imagine. No matter how much greener the grass is on the other side, it’s difficult to shake that fear of failure, of the unknown. You find yourself asking, “what if this dream doesn’t pan out,” “do I have the skills and tools I need to stand on my own two feet,” and “do I have enough money saved as a safety net?” The whatifs creep into your ear, and no matter how hard you prepare to make a move, you might still find that you doubt yourself and your degree of readiness.

Fortunately, I am in a place where I am confident and happy in my work, and since I made the jump from my full-time job, I’ve never looked back. My decision is one that I don’t regret in the slightest, but that doesn’t mean that the process of transitioning away from my standard 9-to-5 job hasn’t taught me many lessons — it has. I’ve had time to reflect on how I spent those last six months at my full-time job preparing to leave, and what decisions (and mental preparation) helped me the most.

Although I have a LONG WAY to go before I understand everything that comes with being your own boss (which is a #journey unto itself), I do feel like I was well prepared, mentally and financially, to make the jump from full-time to freelance. Below are six tips/things to remember, which I feel every budding entrepreneur could benefit from knowing.

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Freelancers and entrepreneurs who are older and wiser than I stressed the importance of building out a financial cushion for myself — one that covered anywhere from six months to a year of bills. Now, I had the very good fortune of not having rent to pay, so it took me a lot less time to build out that cushion for myself than it did for other individuals I knew. To save money, I cut the obvious corners and said “no” to shopping, dinners out, and weekend trips with friends, which allowed me to bank nearly half of each paycheck away into a savings account each month. Aggressive, yes, but I had to make sacrifices in the short-term to realize my long-term goals. That financial cushion allowed me to focus on the work that I had ahead of me, rather than my focus being immediately tainted by the stress of thinking about how I would make ends meet. However, it’s important to remember that your safety net is only a temporary reprieve and six months will pass by quicker than you think. If you don’t have a lump of savings you can tap into, it’s beneficial to have a side gig lined up through which you can make enough money to pay bills and cover essential living expenses. It won’t be easy to face this change, but all you can do it work as hard as you can to ensure it’s only a temporary transitional period.

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Although 9-to-5 jobs can (sometimes) seem soul crushing, what is beneficial about them are the working hours which are straightforward and consistent. Before you leave the regimented structure of your office job, prepare yourself to pull longer hours (if you haven’t already done so) which can overspill into your personal life. Something I always craved at my old job was a breakdown of the barriers between “work” and “play.” Personally, I enjoy my work spilling over into my personal life and infusing one with the other. However, some people do not enjoy this work-life situation, so it’s essential to know your own working preferences before you make a jump. Chances are that when you leave your 9-to-5 job it will be for a career or job situation where you have an increased degree of “working freedom.” Sure, you might have the ability to run out to the store in the middle of the afternoon, or grab drinks with friends at 4pm, but that means work that needs to get done will get pushed out further into the evening — a time when you might not be used to working. It’s helpful to evaluate how you work best, create a rough schedule for yourself, practice making to-do lists, and strengthen your resolve to get things done in a timely efficient manner.

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Over the course of the last few months at my day job, I focused on operating as independently as possible. I was told that the thing most newly minted freelancers struggle with is adapting to their newfound sense of autonomy. To prepare myself for striking out in a new working environment, I practiced being more hands-on in every process, being proactive when it came to new assignments, always following up after meetings and workshops, etc. You’ll find that once you’re out on your own, feeling  like you need to be surrounded by a team won’t jive with the reality that you’re your own boss. You need to learn how to make decisions through a combination of knowledge and intuition, and have surety in your own voice, something that I personally struggled with but has improved over time.

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Part of mentally preparing yourself to leave your day job is to embrace change and new opportunities. I used to take comfort in the fact that things on a day-to-day basis more or less stayed the same, which allowed me to specialize in certain tasks and assignments. However, your skills can start to stagnant and improvement in new areas can move more slowly as a result of the monotomy of daily work life. It’s important to think about how you handle new situations, how you handle being thrown curveballs, how well you power through situations that are new to you, etc. If you are the type of person who thrives on knowing exactly what is coming and when, you might not be ready to leave the routine of a day job just yet.

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One of the most important things you can do before leaving your day job is to truly understand what skills and talents you have gained and strengthened, and how they can translate to your life as a freelancer/business owner, etc. When you strike out on your own, you can’t take any experience for granted, as each one can provide you with potential new learnings and connections. Think about the areas in which you want to do better, how mistakes you previously made can inform your decisions moving forward, etc. The coworkers you leave behind are ones that you may need to call on again one day. Leave on as good a note as you can, collect emails, phones numbers, and any other social media connections you have to.

When it’s time to move on from your day job and onto something on which you’re willing to take a chance, you will truly feel like there is no other option than to pursue the thing you love most. You’ll work your ass off every day to make sure that you don’t fail, because you can’t. When you believe in something and have the tools you need to succeed, a little preparation can go a long way to make your dream a reality.

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