6 Mistakes to Avoid When You’re Self-Employed

Guest post by Evercontact


The appeal of self-employment isn’t a mystery.


Many of us are drawn by the idea of being your own boss, setting your own schedule, and enjoying a relative freedom from the confines of the 9 to 5. Indeed, non-traditional work environments such as self-employment are on the rise and projected to further take over our workforce.


This shift isn’t surprising nor detrimental; in fact, studies have shown that self-employment increases happiness as well as overall engagement. And millions of workers have already taken advantage of the benefits self-employment allows.


That said, it isn’t all roses.


The steps to successful self-employment are often more a trek through arduous terrain than a skip through the park.  As the old adage goes: with great power comes great responsibility… And the responsibilities inherent in self-employment can lead to costly mistakes if one jumps in unprepared.


On that note, here are 6 common mistakes to avoid when self-employed:


1. Falling prey to misconceptions


To continue the train of thought, self-employment’s perks are often mistaken for realities.


Sure, a self-employed route may grant you freedom, autonomy, and heightened creativity, but assuming these are instant benefits would be a gross misconception. Self-employment is a less glamorous utopia and more alternate lifestyle – one that contains all the typical highs and lows of a “regular” job.


And as with any serious job, you’re going to need to put the work in.


On the flip side, it’s vital not to let the chorus of negative stereotypes derail your vision. It’s easy to get swept under cries that self-employment is “too risky!” or “so lonely!” or simply “too difficult!” But anything worth doing comes with its own glaring asterisks.


The key, then, is to do it correctly.


2. Time mismanagement



Without the rigidity of a clock-in/clock-out schedule, it’s easy to lose track of production. That’s why setting a routine and establishing boundaries to your flexibility is vital to success.


In other words, take advantage of working on your own time, but follow the necessary provisions to ensure max productivity. This encompasses not just the focal point of your occupation, but also the nitty gritty bits like accounting or marketing.


That said, while you don’t necessarily have a set morning alarm, you also don’t have a set time to pack your bags. Drawing a clear line between work life and life life is trickier when those boundaries aren’t pre-set.


So set them. “Clock out,” if you will. Don’t let the freedom of self-employment transform into a burden on your personal pursuits and relationships.


3. Misappropriating your workload


As with the previous points, this one comes with two sides to the coin:


On one side, you don’t want to put too much on yourself. It’s easy to lose sight of efficiency and let yourself get spread thin between too many projects and duties.


Self-employment requires you to be a worker and your own boss, the latter of which shouldn’t lose precedence. Keep sight of the big picture, delegate more menial tasks, and funnel your “worker” energy into what’s most important.


On the other side of the coin, however, is the danger of delegating work. Putting your trust in an outside party to complete necessary work is daunting if that trust is betrayed.


This is why proper vetting of clients and careful drafts of contracts is vital to keeping your clients in line. Taking extra time now to acquire reliable contract work can pay dividends by saving time and energy down the line.


(Pro tip: Delegating isn’t exclusive to contractors; it can also apply to apps! This is where a tool like Sanebox comes in handy – organizing your inbox so that you can focus less on email management and more on… well… whatever!)


4. Short term focus



It’s essential to manage your business with a balanced micro/macro approach.


As enticing as short-term profit may be, it’s far from a surefire guarantee of long-term success. Which is, after all, what you’re looking to achieve, right?


So don’t be blinded by the money bags and keep your eyes on the prize. Bolster whatever quick success you achieve with proper branding and marketing techniques, take steps to grow your clientele, and – by doing so – sow the seeds for many fruitful harvests to come.


Self-employment will likely come with ebbs and flows; don’t get too caught up in the gains or bogged down by the losses. At the end of the day, it’s the long-term game that counts.


5. Not staying connected


One of the perceived downsides to self-employment is relative isolation that results, and rightfully so.


No longer are you surrounded by a host of agreeable coworkers on a daily basis, and you might naturally find yourself less exposed to people in your field. The harsh truth is: You likely won’t be able to tap into the institutional networking channels that may exist at an established company.


But that doesn’t mean you can wipe networking clear off your to-do list.


Actually, quite the opposite; you have to embrace your self-starter status and take the extra steps to bridge the gap. Networking is essential for the self-employed, leading to exposure and opportunities your business wouldn’t otherwise obtain.


(Pro tip: Savvy networkers will employ additional tools to maximize their contacts’ value. For instance, Evercontact gives you a leg up by automatically keeping your contacts up to date in your email address book!)


6. Financial recklessness



With the line between work and home life a little blurrier, so too is the natural distinction between business and personal funds. But failing to draw this line is one of the critical money mistakes one can make in the transition to self-employment.


As is treating your income like profit, despite your venture likely posing somewhat of a financial risk, particularly in the early stages. Thus, a propensity for negligent spending and a lack of emergency funds is a good way to sink your expedition at the onset.


Even something as simple as lax accounting can collapse your business’ integrity.


It’s not flashy or exciting, but diligent money management is absolutely vital. You may see it as an onerous task, but it’s a task that demands your attention (especially when raising invoices to your clients).


And while we’re at it, you have to be prepared for the knotted ball of rubber bands that taxes become. Depending on your industry, taxes may present a number of potential headaches once unemployed.


Like we said… self-employment isn’t all roses.


Final word: Do your due diligence


At the end of the day, the only way to avoid costly mistakes is by being meticulous.


You have to understand that self-employment isn’t some romantic vacation; it’s a difficult pursuit requiring tons of work and attention to detail to sustain. And unlike traditional work settings, self-employment relies on you and you alone to set the boundaries, establish workflow, and keep up organization.


But if you’ve read this far, you likely believe what millions of self-employed entrepreneurs know to be true: the hard work can reap tremendous dividends.


So put the time in to avoid the common mistakes; after all, the success of your work lifestyle depends upon it!





Dan Rozenblum hangs his proverbial hat on his writing prowess as he works on developing Evercontact’s content direction. When not obsessing over where he puts his semicolons, this Boston native enjoys reading literature, wandering aimlessly, and moving to new cities.