Four Things I Wish People Knew Before They Quit Their Day Job
You may have the guts to leave your 9–5, but you probably shouldn’t
If you’re dreaming about the day where you walk up to your managers and communicate that you’ve decided to close the door of corporate life, maybe press pause for just a second as I give you a glimpse behind the curtain of working for yourself…
Recently, I have had friends and family share their dreams of leaving their jobs with me, thinking that because I have found ‘success’, that they can too.
I’m not going to tell you that you have no chance of ‘making it,’ because you have scope to truly step into a life that stimulates your mind and makes your heart smile with fulfillment. I’m proof that the grass can be greener on this side of life. But, it’s not the best fit for everyone.
Allow me to share some food for thought that could either guide you in approaching your manager differently or give you the confidence to perhaps quit with a fresh perspective as to why. I am going to walk you through what I wish people knew before they quit their day job. The four points that I will be discussing are what I have observed as major stumbling blocks for those who leap from a normal job to freelancing or entrepreneurship.
If you find yourself being able to securely tick off these points, then I would bet on you to make it. However, if even one of these points causes you a little discomfort, then perhaps consider creating space to address the point and work through it before you step out of a secure working environment.
#1 Are you an introvert or extrovert?
A close friend of mine works for a company where it doesn’t seem like office-life, as they knew it, is going to ever go back to how they remember it. They really struggle with Zoom-life and are miserable working from home. I would consider this person an extrovert, and I would not recommend further isolation for them, even though right now, quitting their job seems like a pretty attractive alternative for them because they think they’re alone.
Working for yourself, especially if you are building something from the ground up, often requires hyperfocus and the ability to spend hours alone while you get things done. Depending on what venture you want to participate in, you may even find yourself pitching for jobs where it seems like a one-way communication and heaps of rejection.
I’m an introvert, and alone-time recharges me. I get excited about pockets of time where I get to jump in a bubble, create and make my own opportunities. For those who can manage, managing themselves, then self-employed life feels empowering. For those who can’t, alone time could become a space of procrastination where checking social media or watching a quick episode of a series becomes a form of human interaction that distracts you from your work.
But, for the extraverts wanting to consider ideas of how to be alone, but at the same time feel a sense of community, then working from a coworking space could be just what you need to stay somewhat connected. Even as an introvert, working from a coworking space a few times a month has been an enriching experience for me.
Ultimately, knowing whether you can work alone, or whether you need human interaction nearby, could set you up for success if you’re planning to make the leap.
#2 Do you have an emergency fund?
Now, I’m not just talking about savings to start your business or having enough money carry you through the first month or so. I’m curious as to whether you have enough money backed up for those unforeseen expenses like when your car needs new breaks or you need to get your eyes tested for glasses?
Most people I’ve met don’t quit without being able to sustain their fixed expenses for at least three months but rarely do these people have backup money because all it takes is one unplanned expense to make life truly uncomfortable.
Realistically, expecting to make it fresh out the gates as a successful freelancer or entrepreneur is unlikely. I used to feel confident encouraging others around me to give themselves at least three months of constant pitching or brand-building. However, these days, the competition pool seems a lot larger and I now recommend expecting the worst-case scenario for at least 6- 12 months.
I prefer to plan cautiously.
This way, you are able to make decisions with a clear mind. Being desperate to make money to cover bills or unplanned expenses could see you making a short-term decision that you’ll regret in the long term.
#3 Are you mindful of the expectation gap?
Having a normal job does provide some level of security. Where I have seen this to be particularly useful is when someone grows comfortable with a certain lifestyle.
Lifestyle inflation is a snake. You may think that you are able to cut down on costs are live life on a shoestring budget, but if your expenses crept as your salary increased, then it becomes a tad tricky to maintain life as you knew it.
A common example I see is people who enjoy getaways or going out. You may think that when you work for yourself, that you will still be able to fund that lifestyle. However, unless you are able to guarantee a sustainable salary, you may find that your income shrinks in the winter months and grows in the summer months as a self-employed individual. This means that you have to start managing your money over longer stretches of time as opposed to monthly.
A more obvious expectation gap is thinking that you will work less when you work for yourself. Most self-employed individuals I’ve met classify themselves as crueler than any boss they have ever worked for. What they mean by this is that they are inclined to expect themselves to work harder and longer when working for themselves. If there is a boss, you can blame them, but when you work for yourself there are no excuses. You have to get the job done regardless of the personal toll it takes on you, otherwise you don’t get paid.
The last expectation gap I’ll share today is that you may think that you will be doing what you love for the majority of the day if you work for yourself. However, you will find yourself having to wear the hat of possibly a telemarketer, an agent, a publicist, a creative, a bookkeeper, and the list goes on. You may find yourself spending hours on tasks that bore your brain to the next level…
However, you may also find yourself being able to outsource tasks you do not enjoy, but then you just have to be mindful of managing others. It is possible to create an environment where you do only what you love, but when you’re starting from scratch, it is unlikely.
#4 Have you had a tough chat with your manager?
Sometimes, quitting is not the best fit, especially if you haven’t first tried to talk through what you’re not enjoying in your current workplace.
If you are unable to have tough conversations and approach conflict with a can-do attitude in your current job, you have to question how likely you are to do it working for yourself. See tough conversations as practice and you may be surprised at the result.
A positive outcome is not always likely, but learning to ask for what you want, and dealing with rejection only builds character. Much like developing muscles in the gym, we get to build resilience and courage the more we practice them.
I personally always try to clean up the mess in my current arena, before jumping to the next arena and hoping for a more pleasant experience. If you can take the punches gracefully where you are currently stationed then it sets you up to approach the next phase of life with compassion and grit. Well, at least from my experience.
Final Thoughts
My heart is for you to realize that diving into self-employment is complicated. It may be perfect for you, but that it may be better to first do some deep work before you make the leap. Or, you may find that you are far better suited to your current job and that a tough conversation or two could help you get what you want, or realize that the job you are in is never going to give you what you want.
The point is, chasing a dream is easy. Quitting can be easy. But, making a success of your side-hustle or startup is not necessarily going to align with the story you envision. It could easily be a nightmare if you do not approach it mindfully.
Whatever you end up deciding, moving slower helps maintain level-headedness. May you have your wits about you as you step into the life you love.
Good luck!
