Transitioning from “9-to-5” to Entrepreneurship

So you’re thinking about making the leap from your boring old day job to the exciting world of entrepreneurship?  That’s great, but before you start buying into the idea that all entrepreneurs do is build companies, cash out and spend their remaining days sipping umbrella drinks on the beach, let’s get a few things straight…

First of all, it should go without saying that entrepreneurship is hard work.  Really, the number of startup concepts that fail should clue you in to the fact that business ownership isn’t all IPOs and stock options.  However, what most aspiring entrepreneurs miss when they envision making the leap is just how difficult it can be to leave the “9-to-5” mindset behind.

The following are a few of the differences that I’ve identified between being a 9-to-5 employee and a startup entrepreneur.  While your experience may be totally different than mine, I hope you find the guidance here helpful when it comes to maintaining your sanity during this challenging transition!

Entrepreneurs don’t work standard hours

I know, I know – part of the appeal of leaving the traditional work force is that you’re no longer a slave to some arbitrary time clock.  Well, guess what?  As an entrepreneur, you don’t work from 9:00am to 5:00pm – you work even more.

Entrepreneurs consistently work longer hours than traditional employees.  And while the passion you have for your business and flexibility of your new work style certainly make entrepreneurship an appealing choice, don’t think that quitting your job is suddenly going to free up hours of spare time to be devoted to leisure pursuits.

For example, right now, I start my days off with a few hours of work from 6:30-9:00am.  Then, I’ll grab breakfast and be back “on the clock” from about 10:30am-4:00pm.  At that point, I’ll break for lunch and/or a trip to the gym before another work session that lasts from 7:00-10:00pm.  But I’m not done yet!  After spending time with my wife or my friends, I fit in one last work session in bed from midnight-1:00am.

Of course, this all depends on my phone meeting schedule, which could shift my daily calendar around entirely.  But at the end of the day, I’m working a hell of lot more hours each day as an entrepreneur than I ever did as a traditional employee!

Now, on the plus side, the flexibility of being a small business owner means that these work chunks can be done from anywhere, leading to one of my favorite things about entrepreneurship – the “workcation.”  Because I can work from anywhere in the world, I’m able to travel whenever I want to, which is a perk that certainly wasn’t available to me as a 9-to-5 worker.

Entrepreneurs are only accountable to themselves

When you work a traditional day job, you have at least one boss peering over your shoulder at all times (or, if you’re really unlucky, seven or more bosses bearing down on you).  If you don’t get your work done, you’ve got to answer to the chain of command, with repercussions ranging from disciplinary actions to outright terminations.

Anyone who’s ever had a bad boss knows how frustrating this type of oversight can be.  However, entrepreneurs who have left standard employment to pursue their business ideas also know that the management hierarchy can be incredibly comforting.  When you have a boss, you have someone to answer to.  You may not like him or her, but you understand your role in the corporate structure and the threat of negative actions motivates you to get your job done.

As a startup entrepreneur, there isn’t going to be anybody else holding you accountable (unless you’ve reached a stage in your company’s growth where you’re reporting to investors or a Board of Directors).  As such, you’ve got to learn how to motivate yourself – even when you’re tired and would rather spend the day lounging on the couch, watching TV.  It isn’t easy, but you really can’t be a successful entrepreneur without this skill.

Entrepreneurs must be masters of all departments

In the world of traditional employment, you may have contacted the IT department for tech support, the accounting department to get your invoices processed and the marketing department for the materials needed to advertise your products.  Well, guess what?  As an entrepreneur, you’re all of the above – and more.

As an entrepreneur, you’re tech support, you’re accounting and you’re marketing – on top of the regular responsibilities associated with building and promoting your product.  Yes, you can outsource some of these tasks, but as most small business owners know, the cost of doing so can be prohibitively high.

So if you’re thinking about making the leap to entrepreneurship, try to beef up your skills in any of these weak areas before leaving your 9-to-5 job.  Ask your company’s IT manager for tips on computer maintenance and find out from your marketing team which programs they’ve used to create your corporate materials.  Then, get good and used to using Google to answer questions that come up when you no longer have a corporate hierarchy to back you up!

Entrepreneurs have to be success-oriented

One of the best parts about 9-to-5 jobs is that – in nearly all cases – there’s some type of wiggle room for bad behavior.  Have a late night out with a few too many beers?  I’m not saying that I’ve ever done this, but plenty of other 9-to-5 employees I’ve known have been able to call in sick or sleep off their hangovers in unused conference rooms – while still getting paid their usual salaries.

As an entrepreneur, there’s no sick time and there are no low productivity days spent goofing off while on the clock.  You’re scheduled to work each and every single day, so that hangover that was a mere minor annoyance while working a 9-to-5 job now means that you’ve either got to struggle through the pain or fail to meet an important deadline as an entrepreneur.

At the end of the day, entrepreneurs must be success-oriented – that is, they must be willing to make the choices and compromises needed to be successful.  Traditional employees have much more wiggle room than entrepreneurs, as these 9-to-5ers are often able to skate by and stay employed without giving a 110% effort.  As an entrepreneur, though, your entire focus must be on achieving profitability as quickly as possible, and that often means making tough choices that prioritize your business over other aspects of your life.

Entrepreneurs must be ready to face failure

Let’s face it – it’s pretty hard to fail as a 9-to-5 employee.  Sure, you might get a negative performance review or some constructive criticism from time to time.  But unless you’re publicly shirking your duties or violating some major guideline with your company’s employee handbook, it’s actually pretty tough to get fired from most jobs.

Entrepreneurs don’t have that luxury.  In fact, as a startup owner, you’re lucky if you only fail a handful of times before finally happening upon a viable idea!

Actual failure and the risk of failure both take their tolls on entrepreneurs.  Not only do most entrepreneurs take on significant financial risk to pursue their business ideas, failures affect once-hopeful business people on a personal level.  Watching a seemingly-lucrative idea circle the drain and die – and then picking up and moving on to the next idea – takes a certain kind of strength that most people just don’t have.

If you’re thinking about making the transition from traditional employment to entrepreneurship, think long and hard about whether you’ll be able to pull the plug on failed projects when you have to, as well as whether or not you’ll be able to own up to these failures to the friends and family members in your life who are counting on you to succeed.

Entrepreneurs need exceptional stress management skills

If that last section scared you a little bit, that’s good.  The last thing you want to do is to transition into the world of startup ownership without being fully prepared for the very real risk of failure.

However, what should also be apparent by now is that entrepreneurs face substantially more stress than nearly any 9-to-5 worker.  But even if you do work in one of the traditional professions deemed most stressful (as in the case of paramedics, heart surgeons and other high-risk fields), you still have the reassurance that you’ll receive a steady paycheck every two weeks for your troubles.  Most entrepreneurs won’t see this type of reward until at least a few years in.

Really, everything about entrepreneurship is inherently stressful.  Therefore, if you’re thinking of making the leap into the field, you’ve got to have a system in place for managing excess stress.  While you’ve got to work hard and deal with risk, you also can’t let this stress translate into illness or burnout.

Fortunately, you can practice these necessary stress management skills as a 9-to-5 employee.  Take up yoga, learn to meditate or try a kick boxing class – do whatever it takes to find an outlet for the anxiety that comes along with entrepreneurship in order to make your business a sustainable option for the long run.

Entrepreneurs must account for social interactions

Another thing that’s always startled me when alternating between 9-to-5 jobs and entrepreneurship is the amount of social connection that’s lost at first.

When you’re a traditional employee, you probably don’t even notice how much of your time is spent gossiping with other employees and shooting the shit around the water cooler.  But trust me; you notice it when those vital social connections are no longer there to support you in the early stages of a startup launch!

At Single Grain, I’m lucky to have my staff around me to provide some much needed social interactions.  However, if your startup hasn’t yet reached the stage where hiring employees is a viable option, you absolutely must make an effort to get out and spend time with people.  Join a coworking office or organize meetups with other entrepreneurs – just make an effort to maintain some social ties, lest you wind up like this.

Entrepreneurs are responsible for their own benefits

This last consideration is more of a practical concern than the mindset differences I’ve described above, but it’s still an important item to be aware of.

While it’s pretty well known that entrepreneurs are generally responsible for their own health and dental insurance, there’s a whole host of other employer-sponsored benefits that entrepreneurs need to consider replacing.  For example:

  • Life insurance – Most people get their life insurance from their employers, which means that if you leave the fold, you won’t have this coverage unless you seek out a private option.  If you’re single and completely free from debt, having an active life insurance policy might not be necessary.  But if your passing would leave loved ones with unexpected bills, be aware that you can find these policies through all sorts of organizations pretty cheaply.
  • Disability benefits – But don’t just worry about what might happen if you were to die unexpectedly.  Worry about the possibility of an unanticipated disability, as young workers are significantly more likelyto become disabled than to die and are often unprepared for the financial ramifications this entails.  Nearly all entrepreneurs are underinsured in this area, and while it’s more difficult to find private disability insurance than private life insurance, it’s something that all entrepreneurs should consider.
  • Retirement account contributions – Finally, leaving a 9-to-5 job often means leaving the cushy retirements that come along with it (if you were lucky enough to get them in the first place).  And while contributions are usually one of the first things to go when it comes to the entrepreneurial slashing of budgets needed to survive on a limited income, think carefully about the lost potential for compounding that you’ll only have while you’re young.  Setting aside even a small amount now can be just as effective as contributing larger amounts much later on.

I’ve said on this site before that I don’t believe entrepreneurship is right for everybody, and hopefully the challenges described above identify some of the reasons behind this.

But if you are interested in pursuing your startup idea, know that I’m not saying any of this to discourage you.  Personally, I’ve found transitioning from 9-to-5 work to business ownership to be incredibly rewarding – though not without its own unique challenges.  Before making the leap, consider coming up with an action plan to address the issues described above in order to start your new business off on the most stable foundation possible.

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About Sujan

Sujan Patel is the VP of Marketing at thisCLICKS, the makers of When I Work & Wage Base. Previously Sujan founded Single Grain, one of the top Digital Marketing agencies in San Francisco, CA. With more than 10 years of Internet marketing experience and has led the digital marketing strategy for companies like Sales Force,…