The Employee vs. Entrepreneur Showdown Starts Now! And the Winner Is…

The employee vs entrepreneur showdown

The Employee vs. Entrepreneur Showdown Starts Now! And the Winner Is…

Image Caption: A man on his morning commute in Atrani, Italy. Whether he’s an employee or entrepreneur is hard to say, but when I ran by him, he seemed pretty happy. 

Next LYL World Tour stop, day 165: Tomorrow we leave Capri, Italy en route to France. Our next Live Your Legend meetup is in Paris on July 2nd (with my good friend Leo Babauta of Zen Habits). If you’ll be in Paris, RSVP here to join us


Now time for today’s showdown!

For this to work, I need you to answer an important question on LYL, that hopefully spurs some healthy (and even heated) debate…

Would You Rather Be an Employee or an Entrepreneur?

Live Your Legend’s purpose is to help you find and do work that makes you come alive. Whether that’s as your own boss or an employee in a much bigger company, makes no difference – as long as you believe in what you do and it makes you happy.

But whether you work for yourself or for someone else is a really important decision to think through – one that’s often glossed over and filled with assumptions we might not even know we’re making.

That’s where you come in – for today’s Ask the Reader Showdown…

The Live Your Legend community is a two-way street, so today, instead of me providing an attempted answer, I’m turning the tables around and asking you to tell us yours in the comments. Your response will not only likely help shed some light on your own thinking, but also add some new perspective and clarity for the rest of us.

Plus, it will give me a much better feel for the types of topics I should cover for you in the coming months on LYL (I always try to create what you tell me you need the most help with).

So right now, please take a few minutes to answer these two questions in the blog comments:

(You’re welcome to use an alias if you’d feel more comfortable being anonymous.)

1. Would you rather be an employee or an entrepreneur?

2. Why? Give at least one reason why you want to be one and don’t want to be the other. (the Why is the most important part!)

If you don’t know which camp you’re in, that’s fine too, but still let us know what’s on your mind and why you’re leaning one way or the other. It’s time to get the gears cranking. 🙂

And if you already have experience as one or both, please share that in the comments, as honestly and vulnerably as you’re comfortable with – what’s surprised you (the good, and more importantly, the bad), what’s been awesome, what’s been awful? This especially goes for you entrepreneurs in the audience, since our role tends to get more over-glamorized than the employee’s.

Share your answers in the comments below!

The experience of many is much more useful than the experience of one.

That’s the point. Explore your own answer and enlighten us in the process.

Then I promise to take what I learn from you and incorporate it into what I create at Live Your Legend going forward.

And for bonus points, check out the other comments and reply to one where you think your insight and experience might be helpful.

Remember, you get as much out of this community as you put in!

Thank you for always doing your part – We’re much stronger together.


– Scott

So… Do you want to be an employee or an entrepreneur, and WHY?

Tell us in the comments below & get in on the showdown!