Entrepreneurship – Get “Real”

Entrepreneurship – Get “Real”

Get Real

Recently, an entrepreneur colleague/friend (who I will admit that I idolized) decided to walk away from being an entrepreneur and take a job at someone else’s company. I was, frankly, heartbroken (because when the most hardcore entrepreneur you know packs it in, it makes you stop and think).  It brought to mind a conversation he and I had  a couple of years ago about people (often very well-meaning people) telling entrepreneurs, especially solopreneurs, to “get a ‘real’ job.”

Here’s what people tend to see as a “real” job:

  • Employer makes the schedule – Employee has to work when the employer dictates.
  • Employer supplies the office space.
  • Employer buys the necessary supplies/equipment to do the work.
  • Employer can decide, at any time, for any reason (or no reason) to terminate your position.
  • In short, a job where you go to an office every day for a set length of time and do what someone else dictates.

There are other components, but those are some of the big ones. And most of them are also used as criteria by the IRS as to whether someone is an “employee”.

But, as an entrepreneur, you might see that ‘real’ job a little differently. Here’s what you might see:

  • Employee gets a paycheck as long as they do a passable job.
  • Employee gets to work during business hours and (generally speaking) doesn’t take work home.
  • There’s a janitorial staff, an accounting staff, HR staff, administrative staff and they take care of the nitty gritty details behind the scenes.
  • There’s very little risk for the employee. If the business fails, it’s not their fault as an individual.

Traditionally employed folks (defined here as people who work for someone else), especially those who have never had an entrepreneurial venture tend to see entrepreneurs as folks who have a “cushy” job. I’ve heard all of the following:

  • No time clock – lucky you. You can work as little as you want and whatever hours you want.
  • You get to work from home, or the coffee shop.
  • You can work in your pajamas every day. (Well, maybe not at the coffee shop….)
  • If you want to take off and go to the beach, no one can tell you no.

And, admittedly, there is truth to that. When you’re an entrepreneur, no one dictates your schedule or your dress code. But let me clue you in to some of the reality of being an entrepreneur:

  • At least when you start out, there’s no one else to do any of the work. It’s ALL yours to do.
  • If you’re not working, then you’re not logging billable hours and you have no income.
  • Sick days? Vacation days? See the point above – you’re not getting paid if you’re not working.
  • Computer crashes? Printer stops working? There’s no IT staff. You fix it yourself or have the expense of buying new equipment.
  • If the business fails, it’s on your shoulders – the risk is all yours!

I do not, at all, want to make being an entrepreneur sound like a bad thing – there are tremendous perks:

  • Do a fantastic job and your client loves you? That glory is yours to bask in!
  • Need to go to an event across the country (or across the world?) If you have a laptop and an internet connection, you can work from pretty much anywhere.
  • No dry cleaning bills, no high heels required, no expensive wardrobe needed.
  • No sitting in traffic. No being at the mercy of a bus or train schedule.
  • If you do something you are passionate about and that you love doing, it’s completely worth it!

Sure, I may not have a posh office and a guaranteed paycheck, but the work I do is VERY real. And my love for what I do is very real, as well. I’ve heard it said that “An entrepreneur is someone who will work 100 hours a week for herself to avoid working 40 hours a week for someone else”, and so many times I find that rings true. And if that sounds not only “ok”, but the thought exhilarates you, you might want to try being an entrepreneur!

I wish my friend, the former entrepreneur who has entered Corporate America, all the best and know that, in our own ways, we will both achieve ‘real’ success and happiness.


  • Aaron Plaat says:

    August 12, 2015 at 8:59 pm

    Excellent blog! I’m actually glad you took the time to jot down these thoughts, as they echo a lot of my own on the whole job/entrepreneur struggle.

    Turning the clock on 8 years of self-employment, it was a really tough struggle to get a dreaded j-o-b, however there were some very clear reasons why I took one instead of the traditional entrepreneurship route.

    1.) Innovation – TripleSkinny had reached a very successful point where I had to decide whether or not to grow the brand as a full-fledged digital media agency/consultancy, or to bury the hatchet in the business because it had reached a very stagnant – albeit successful – level of innovation; I wasn’t doing anything new anymore. And the things that I had done that were more innovative (e.g. WP as a powerhouse, FB marketing hacks, etc) were now being adopted by other companies and it was no longer ‘new’ and unique.

    2.) [in]stability – When you shift from being a ‘solopreneur’ to taking on portfolio projects; e.g. growing teams of employees and having a large-scale go-to-market plan for your business, a lot of times the beloved solopreneur career takes on life of its own and begins to look more like a job than a self-employed career.

    I recognized that several of the projects I was working on had all of the elements of regular jobs; an office, staff, HR, payroll, etc., however as the ‘founder’ a lot of the perks of a job (mainly…income) were the last thing to roll up the ownership tree after all expenses are paid.

    3.) Team dynamic – at the right job (really, a startup) you are surrounded by a diverse group of people that help better yourself a lot more than the articles/books/videos I’d watch by myself. It forced me to get ‘outside my head’ and learn from what others are doing.

    The team element is a really important structure many solopreneurs fail to integrate into their own lives, and I’m the perfect case study example;

    A lot of seemingly-brilliant ideas were actually horrible. However, when I was whiteboarding until 3am, they seemed viable and exciting. Looking back, I’m SO thankful that I decided against turning TS into a hosting/WP training business, because I had zero passion for those two industries.

    4.) – The ‘right’ job: this one is a bit hairy, because taking a job often appears as an umbrella statement.

    What I love about working for/at/on a startup is the flexibility. Here, I can still wear a million hats, in a very entrepreneurial/intrapreneurial way, while maintaining growth and forward movement, as a whole.

    5.) – Multiplication. This is really what was the kicker for me. Even at the height of TS success, I was still limited to the revenue that was brought in that month/quarter/year, there was very little scalability or long-term projected growth. In the startup environment, the benefit of stock options really help employees see the long-term value behind their work. It also gives you something to look forward to as you see the valuation increase as the company grows.

    That was a really important part for me, because even though the up-front financial benefit might be smaller at a job, the long-term play is significantly greater.

    6.) Freedom – this is the biggest benefit I had during my time at TS; being able to take midday breaks, adventures, etc. was a nice perk. However, I really never had weekends to enjoy and completely ‘check out’ because I was always on the clock.

    Now, I still enjoy 99% of the schedule flexibility I had and can FINALLY enjoy weekends without any sense of guilt.

    …when your phone burns down at a campfire, you have no worries because your clients can’t get in contact with you.

    While it’s not the case for everybody, I think that working at the right startup is a positive advancement, as an entrepreneur, and not a step backwards.

    At the end of the day, only one thing matters…

    Hustle, son.

  • L Darkstar says:

    August 12, 2015 at 9:21 pm

    Aaron– Wow! I almost feel like I should have let you write a guest blog post!

    I think one of the best things about life in general is that there isn’t just one path to happiness.

    I’m glad you found your happily-ever-after (or, you know, as close as any of us get) and wish you every success!

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