Not having to set an alarm. Avoiding the daily commute. Working in your pajamas from the comfort of your home. Does any of this sound like music to your ears?
Most people will at some point in life entertain the idea of being their own bosses. A shitty job experience in the past can be enough to trigger such thoughts — or simply reaching a point where dealing with orders from above is enough and trying to carve your own path becomes attractive.
Others might even feel shackled by the traditional 9 to 5. In its 2017 State of Telecommuting in the US Employee Workforce report, FlexJobs found that “3.9 million U.S. employees, or 2.9 percent of the total U.S. workforce, work from home at least half of the time, up from 1.8 million in 2005.” This non-negligeable 115% increase in a decade opens our eyes to a new mentality about work that perfectly syncs with technology breakthroughs.
It seems workers value freedom and flexibility greatly; above almost anything else. Can we really blame them? Unless you want to alienate a whole group, it might be time to reconsider the old ways and embrace a shifting paradigm. Work doesn’t have to be seen as castrative or only as a means to an end; nurturing positive environments where you can grow both as a human being AND professionally speaking is what businesses should aim for — requiring a will to adapt, but not blindly so.
However, independence comes at a price.
Standing on your own feet: considerations & preemptive measures
Before you decide to forge your own path and be the master of your own destiny, there are some important things you should be aware of. Not being tied to an office and taking on all responsibilities now as your own boss might be right up your alley, but it’s not always a walk in the park.
Hit or Miss Productivity
Being your own boss means you have to deal with all aspects of your business. Unless you have iron self-discipline, distractions can really hinder your productivity — doubly so if you’re working from home, endlessly tempted to watch just one more Netflix episode from your favorite series, playing that ever-so-addictive video game while you’re supposed to be working, or just downright chilling at the wrong time.
It’s easy to lose focus and motivation … therefore, developing good motivational strategies and a plan is pivotal to successfully being your own boss.
Preemptive measures: have a real working place (i.e. not your couch) and schedule your days in advance. Always remember why you wanted to be your own boss in the first place so you have the motivation to push forward even during lulls or difficult times. Set some goals you want to reach; write it all down or use software like LifeTick.
Mental and Physical Health
Not everyone is fit to be a leader and choosing the entrepreneur way is a real challenge. You’re going to feel pressured, your patience will be put to the test. How you rebound after failures will dictate whether or not you can hope to be successful.
Beyond these preoccupations, you might feel alone, like a one man army. Independence can take its toll on you. Good mental health has many benefits, including a greater ability to enjoy life, cope with difficult times, higher self-esteem and more energy to spend on things that matter to you.
By acting on your own, you might pick up some bad habits along the way … like adopting a sedentary lifestyle, for one.
This is especially true in a world where almost everything can be done with the help of computers. Groceries? Check. Online shopping? Check. Sex? We’ll leave that one to you…
Preemptive measures: work on your relationships. Humans are social animals so you actually need to interact with others at some point. If you have the chance, meet with like-minded people at least once per week. Find a hobby and join a club. Get out of your house. Also, don’t underestimate physical activity. Even just a few minutes a day is good for the body. Try to exercise often and you will see the benefits. An appropriate diet will also improve your overall health.
“’Tis impossible to be sure of any thing but Death and Taxes,” – Christopher Bullock (1716).
Nobody likes taxes; and as an entrepreneur, you’ll learn to absolutely loathe ’em. The paperwork involved is annoying and can really come back to bite you someday if you’re not careful.
When you first start, paying an accountant might be out of your budget so be prepared to dabble in numbers. Prepare for long nights sorting out your bills unless you’re well positioned and prepared.
Preemptive measures: make sure to read everything related to taxes as an entrepreneur in your region. For instance in Quebec entrepreneurs must pay taxes in advance (tax instalments) if the total due is estimated to be higher than $1800 CAD. Leave all your important files in an easy-to-reach place, preferably a filing cabinet. For your online documents, apply the same logic: put everything in properly organized folders.
Paying out of your own pocket
Entrepreneurship ain’t cheap. You must be ready to invest money and cover a wide range of unexpected expenses. To name a few: furnishing, electricity, phone, Internet, etc. Having your own business really opens your eyes in regards to costs and how they can cripple your budget.
Preemptive measures: have enough money to sustain yourself for a couple months— including rent, food, etc. The last thing you want is to run out of funds because you didn’t account for all the costs of being your own boss.
Benefits = gone
Another huge mark against independent work is the loss of employer benefits, including health insurance and employer match retirement plans. As your own boss, you’ll need to fork over some money for private insurance. That might not be the end of the world for everyone, but it can indeed be a curveball to those who were once traditionally employed.
You’ll get acquainted with all sorts of unplanned expenses… and fast.
Also of note is how you must be ready to work even on weekends, meaning your vacations will be cut short or simply non-existent. At least if you want to be successful, which requires commitment and focus.
Preemptive measures: shop around for health insurance BEFORE making the jump from employee to entrepreneur. Compare your actual benefits to what you’ll be able to purchase on your own: a willingness to make some sacrifices is in order. List your priorities, for example do you care about a dental plan or not? Do you need vacations in your life? Answers to these questions will help you in setting up a realistic plan of what to expect.
The joys of being your own boss
Now that the challenges of entrepreneurship are behind us, let’s look at the many reasons why people — maybe even you — still think it’s well worth the trouble to act as a lone ranger.
Total control over your own destiny
Free as a bird
It’s the next best thing to be
Free as a bird
– The Beatles
For most entrepreneurs, choosing when and where they work is the #1 perk, simple as that. As your own boss, you set the hours, choose a work style that suits you and deal with every part of the business. In other words, you’re the sole captain at the helm. Don’t want to deal with a certain client? Your call. Need to take the afternoon off for a medical appointment? You’ll take the messages later. The flexibility is incredible.
Boosted pride and motivation
You don’t want to fail, hence why you’ll pour heart and soul into your own venture. You’ll be spending money you worked hard to pile up, investing time you’ll never see again. Every single achievement — no matter how small — will feel great because it’ll be all on you and you only!
Not to say you can’t feel proud while being part of a great business, but when it’s your baby there’s no doubt a greater sense of accomplishment. Even more so in the face of adversity— and we know entrepreneurship is no walk in the park.
The sky’s the limit
As your own boss, there’s no limits to how far you can go up (or down!) while in a traditional work environment you’ll be confined to your job title, both in terms of salary cap and responsibilities. Instead of fitting into a mold, you’ll be creating one for yourself.
Career progression in a company follows a mostly straight line whilst as an entrepreneur, you can easily — and hopefully — ascend much faster. That’s a bit like taking the American Dream ethos and applying it to your personal life: prosperity through hard work — without artificial barriers.
As an affiliate (except for some fringe cases), you’re already acting as your own boss.
Which brings us to the following question: how has your experience been so far?
To those livin’ the dream, don’t hesitate to share your storied history about what it took to finally get to the driver’s seat of self-employment and financial independence.
Maybe you have some excellent tips for the aspiring self-bosses out there to forge their own destiny? Share with us in the comments below!