Thinking of taking on self employment? Here are 5 questions to ask yourself before leaving your job.

1. Is it the work that bores you to death, is it your boss that makes you perspire profusely, or is it something else entirely?

Before you quit your job, take a second to pinpoint whether your decision to leave is based on something making you unhappy and what exactly that is. It could be the position you hold now, or a lack of challenge in that role. It could also be a nightmare boss that makes you sweat and dread coming into the office. Perhaps it’s the industry you’re working in now that no longer interests you. Be sure that a switch to a new position or new industry isn’t what’s going to scratch the itch.

Many people feel overwhelmed or stressed at their job and it can be completely normal. However, if your boss, and not your work, is your persistent source of anxiety, this can be a bad sign. If you constantly find yourself rethinking what you’re going to say to your boss or how you’re going to say it, they may be putting too much pressure on you. Your relationship with your superiors should be professional, of course, but it should still feel comfortable. It can be draining to work in an environment where you don’t feel as if you can be yourself.

If you think your boss may be the reason you want to leave your job, consider taking a personal leave or leave of absence. This could give you some much needed perspective. Taking a step away from the office (and hopefully into somewhere sunny and calming) may help you analyze your situation with more clarity. During this time, consider what about your boss makes you want to quit? Do you really want to take on self-employment or do you really just hate your superiors?

All in all, if you’re constantly stressing about your boss, you can’t get the most out of your career, which, after all, is what you should be shooting for. Simply put, an environment of discomfort, anxiety, and high pressure is typically not conducive to a fulfilling work-life, at least not in the long term.



2. Do you avoid looking at your bank account? Do you even know how much is in it?

If you frequently avoid checking your balance or get anxious when bills arrive, that’s a pretty big red light that you may not be prepared to leave your job. How comfortably do you pay your bills each month or buy your groceries each week? If you’re contemplating self-employment, be prepared to be on top of these things because it will become especially important once you no longer have a guaranteed salary or stream of income.

Take a look at the benefits that come with your job. Think health insurance coverage, discounts on things like gym memberships and nice-to-haves like stipends for transportation and commuting. Once you leave your job, you’ll need to account for all of this independently, so make sure you know what your costs really are!

If you don’t have a financial plan in place, think about getting assistance and taking time to sit down and map out your plan. What are your short and long term financial goals? How much do you plan to make independently? How much do you need to make to stay afloat, buy property, or have a pet? How often will you pay yourself a salary and how much goes into saving? If all this sounds overwhelming to you, you might consider getting assistance from a financial advisor.

I worked with The Financial Gym after I first left my job to sit down and assess where I was, where I was headed and what I would need to do to stay on top of my expenses. I cannot recommend them enough because they have experience working freelancers, part-timers, you name it. That, and they check in on you on a quarterly basis, so you can say goodbye to that bad habit of neglecting checking your bank accounts 😉 Let’s just say I thought I knew what my expenses were and where my money was going but after my session with my trainer, realized how little I really knew about my money!

If you want to try out their services, they offered me a discount code where you can sign up for a consultation call and get 15% off a 3 month membership using “veggiekins15”.


3. Do you really need to be buying a vegan, whole grain, gluten free, sugarless scone from Whole Foods each morning or will cereal suffice?

One of the inevitable results of leaving a job is a more, let’s say, frugal approach to your current lifestyle. Trust me, you’re not the only one that splurges on coffee or breakfast on their way to the office. But seriously, ask yourself if these are sacrifices you’re willing to make. Maybe you’re making comfortable or good money at your job. Are you willing to put some of your day-to-day luxuries on hold? Many people will answer, “no,” and that’s okay. It’s all up to how unhappy you are at your job. Are you so unhappy that you’re willing to sacrifice the little splurges? It’s up to your personal prioritization.

This CNBC article can give you a better idea if self employment is a financially feasible option for you right now. As the article suggests, consider how much money you need to afford your life, find ways to make money after you cash your last check, expect the unexpected, and plan for the future.

My Financial Gym advisor encouraged me to make a list of my monthly expenses like rent, utilities, memberships and bills. She also had me list expenses that are let’s say… not quite as essential as the above but things that I enjoy and am not willing to give up each month. For me, that was edible flowers and Sweetgreen. It’s okay to include these in your budget, as long as you’re aware of your spending habits and you narrow them down to a few extra things! Treat yo self … responsibly!


4. Are you already putting time into a side-hustle or other passion project? Will you continue to enjoy it once it becomes a primary source of income?

If you’re already putting in a large percentage of your time and effort into a side-hustle, this might be a sign that you’ve already mentally checked out of your current job. Before you make the jump, think about whether that side hustle will still be enjoyable once it becomes a greater source of income for you. Is it enjoyable because it’s a hobby and something you do for fun? Would you still enjoy it if you had to do it all day for example, or given deadlines and contracts around it? Make sure that what you plan to do instead will not become unenjoyable like your current job.

It’s also a good idea to think about whether this side-hustle is feasibly something you could turn into a larger source of income. If the opportunity is part time, ask yourself whether there is room to grow or space for it to become a full time gig because once you leave, it no longer becomes a nice additional source of income, but your primary source of income. Either look to grow and scale up your side-hustles, or take on more opportunities.


5. Does the song, “Closing Time” dance around your mind as soon as the weekday clock stikes 5 p.m.? Or does it feel like walking on coals as you trudge from the train to the office each morning?

Making the switch from a corporate job to self employment is kind of like making the transition from highschool to college. Remember your first year of college when you had to make the adjustment because teachers were no longer on your case about turning in assignments and you had to become responsible for motivating yourself? The same applies to self-employment.

Once you leave the corporate world, you no longer need to work during set hours, wear office attire, meet deadlines, or work 5 day weeks. These are luxuries and definite benefits to self-employment (hello 4 day work week and mid-day workout classes!), but it’s easy to lose sight of your work once flexibility increases. Be honest with yourself and make sure you have enough drive and self-discipline to get things done. If your bed entices you and wearing pajamas makes you want to Netflix instead of work from home, consider joining a co-working space or working on your motivation.

Leaving the house and putting on real clothes may be the push some people need. If you feel like a co-working space may motivate you, look for options in your area. If you’re a New Yorker, this article can give you some good ideas. Remember, though, that a co-working space is an extra expense, and as I mentioned above, it’s something you will have to factor into your monthly expenses. At the same time, just like a pricey gym membership may motivate you to exercise, paying for a co-working space may encourage you to put in work.

Hope you found this helpful!



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BY Remy • April 24, 2018

5 Questions to Ask Yourself Before Leaving Your Job

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  1. Vallery says:
    This is great Rémy! I’m asking myself these questions now :)

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Hi there, I’m Remy! Welcome to Veggiekins Blog, home to nourishing vegan + gluten-free recipes and tips to live your best balanced and holistic life. I’m a human on a mission to empower you to be well and be kind to your mind, body and soul with the healing power of plants.

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COPYRIGHT © 2020 Veggiekins   ☼   Website by Sunday Stories