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Are you ready to be your own boss?

Feb 5, 2018 Sheryl Posnick

Are you ready to be your own boss?

Let’s be honest: if you have a job, you have boss issues. Even if you like your boss, even if you work well with your boss, even if you are pretty happy at work… there will inevitably be some kind of disagreement or frustration. It happens to literally everyone. When these issues pop up, whether serious or just mildly annoying, you might fantasize about what it would be like to ditch the aforementioned boss and go your own way. But not everyone is cut out to be their own boss for real. Before you quit and commit to the ideal of the boss-free lifestyle, let’s look at some of the questions you should ask yourself first if you’re serious about making this work.

Does your personality mesh with the freelance life?

Remember that once you embark on your new career as a business owner or freelance professional, it’s going to be just you taking care of everything. That means your own personality is going to play a large part in whether this is truly the right choice for your career. If the answer to any of these questions is “yes” or “kinda,” then you might want to reconsider making the jump right now.
  • Do I need a lot of guidance in setting my own tasks—and finishing them?
  • Do I need a lot of input from others before I can get started on a project?
  • Do I give up quickly if a task is difficult?
  • Am I hesitant to ask other people for things?
  • Do I panic when things go wrong?
  • Do I have trouble prioritizing projects or tasks without input?
If the answer is “yes” to all or most of these questions, there’s no shame in that. And it’s not a dealbreaker. It just means you’re likely not ready (yet). These are all things you can work on overcoming, if your goal is to be more independent and take-charge in your work life. But when you become your own boss, you already need to have a pretty self-directed working style.

Where do you get your validation?

After your personality, it’s time to consider what makes you feel valued, and what motivates you, professionally. Ask yourself the following questions:
  • Am I driven by my own sense of ambition or self-satisfaction?
  • Do I need positive reinforcement from others to feel like I’ve done a good job?
Again, needing an external source for these things isn’t a personality flaw. But if you are someone who takes validation and feelings of success from how others see you, then you might not find the boss role very rewarding or fulfilling. Being honest about what drives you is the key element here.

What’s your social style?

If you’re going freelance, there’s a good chance that at first it’ll be just you in your home office, or whatever space you’ve set aside for your new work life. And I can assure you that while pets are great, they’re not really helpful when you need to bounce ideas or chat about last night’s awards show. Here's what you need to ponder:
  • Am I prepared to chug along solo for long periods of time, with no coworker chat breaks or face-to-face interactions to break up the work day?
  • Am I okay with most work communication happening via email or phone?
  • Do I need a lot of feedback from others throughout the day?
  • Do I feel lonely if I don’t have much interaction with others during the day?
And if you’re the boss, it can also mean having to shut down distractions around you as well, if your new work environment has disruptions like family members, loud noises, etc. Being the boss means you’ll likely have to both embrace and enforce the solitude factor as necessary to get things done.

Are you prepared for a boss-level workload?

The main difference between being the boss and acting like a boss is the workload. You can fake-it-till-you-make-it on a lot of things, like confidence. But the work you do is going to be challenging when you’re doing it on your own.
  • Am I ready for long hours, or potentially working on weekends or holidays?
  • Am I prepared to be a jack-of-all-trades if necessary, or do I prefer to stay in my lane?
  • Am I prepared for the frustrations that can come with being in charge?
  • Do I feel comfortable managing others?
Realistically, work-life balance may be one of the toughest things to manage if you’re out on your own. The 40-hour work week (or whatever you’re accustomed to now) will likely balloon, once you’re doing the work of managing your business on top of the day-to-day operations of your job. If the idea of answering emails at 10 p.m. makes you want to hide, then you might want to reconsider your readiness to take this step. And if your business expands and you end up taking on employees or other contractors, you need to be prepare to manage them as well—not just yourself. Being the boss means keeping everyone focused on getting the work done.

What’s your financial personality?

One of the most important factors to breaking out on your own is the financial aspect.
  • Am I prepared to handle the logistics of income/payments, taxes, benefits, and accounting?
  • Am I financially literate?
  • Am I ready to make sacrifices if things don’t go well, financially?
  • Am I good at paying bills on time?
These are basic infrastructure questions. Whether you work for a big company or a small one, there are departments and policies in place, and usually there are people whose job it is to handle different aspects of workplace necessities like paychecks and benefits. When it’s a company of one, guess who’s responsible for all of that infrastructure? It may be possible to outsource a lot of the paperwork and financial details, but it will still require a degree of organization and management on your part. Being the boss means owning every aspect of your business, because your name and reputation will be on every document, every contract, every customer or client relationship. If you’re not very solid on financial issues (or don’t yet have a plan to become so), then you might not be ready to be the boss just yet. If you’re considering busting out on your own, there are lots of things to consider: your business plan, your finances, your future career goals. But before you even get to the point of nailing those down, you need to do a brutally honest assessment of whether you’re emotionally and personally ready even to start that journey. Being your own boss can be incredibly rewarding, and just may be the jump that your career needs. However, if you’re not ready to commit to all of the challenges as well as those rewards, then it just might not be the time to do this. And if you’re just not ready yet, it doesn’t mean that you never will be the boss—it just means there’s a little work to do in the meantime.

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