21 Questions: Is Self-Employment Right For You?

Why I Chose Self-Employment over Being an Employee


Are you meant to work for yourself or for someone else?

Would the lifestyle and working style of self-employment fit you or undo you?

Or would you be your happiest as a stellar employee for your favorite company?

Much like getting married, having children, or traveling the world, self-employment is NOT for everyone either.

In fact, it may be the poor choice at one phase of your life but the ideal choice at another. You change and evolve over the course of your working years and so asking this question at the right time is what matters. Where do you stand today? Where will you be in the near future? Is there a way to find out?

For me, when I was that devoted corporate employee, I could never see myself as an entrepreneur! It was all about rising on the corporate ladder for me so the idea of not working for a large Fortune 500 company and belonging to a colossal entity scared me to bits.

Except slowly, I started to feel this insatiable hunger for doing meaningful work, something I could not find in all of corporate. I changed jobs, bosses, projects and teams several times, and I just got hungrier over time. I finally accepted that I was a total misfit for work in the corporate structure so even if they offered me the world, what did it matter if I was in the wrong place?

Whatever it is I was meant to do was not in the vast corporate landscape, that’s for sure but where was it?

That’s when my entire perspective on success shifted. The idea of building a business from scratch started to appeal to me like a newly discovered taste that had been missing from the nourishment of my soul (If you think I exaggerate, you haven’t known the true hunger of your soul yet, and I’m happy for you!). I grew tired of a decade plus quest in Corporate America overnight. I was done working for someone else for good.

Looking back, I know for an absolute undeniable fact that I was made for self-employment but I came to it through a maze and ended up in the right place from the pain of being in the wrong place and not so much with the intention and foresight that one wishes to have on such decisions.

So in this blog post, I want to give you the foresight I learned along the way. Let’s find out with these questions if entrepreneurship is right for, if it fits your personality, your desires, and your vision of what work is supposed to be. Shall we?

21 Questions to Find Out if Self-Employment is For You

Instructions: Read these questions slowly and out-loud. Digest them slowly. Imagine the scenarios and the circumstances. Picture how you would feel and react to each. Remember what is important to you and what values you hold near and dear to yourself and ask yourself whether the question weakens or strengthens that position. Then reply with your answer.

These questions are in the format of True/False where True is a plus mark for Self-Employment or working for yourself and False is a minus mark for it. Note: a minus on the entrepreneur side does not necessarily translate to a plus for a corporate job.

Last but not least, be honest with yourself, go with your first instinct as it’s usually the right one and the rest will take care of itself. Good luck!

1. You want to call the shots and do things your way because you get extremely motivated by pursuing and implementing your own ideas.

2. You prefer flexibility and freedom in your work-life schedule to a company-mandated structure.

3. You want to have the responsibility to choose the smartest and most efficient systems and tools to get your work done.

4. You get extremely bored and frustrated at meetings at work because you feel it accomplishes nothing.

5. You want your opinions to matter without having to run them through the filters of a team, a management or an organization.

6. You would trade in an easy boring job with the challenging, hard-working sweat-&-blood inducing pursuit of your passions any day of the week because you hate doing mindless tasks for someone else more than doing insanely hard work for yourself.

7. You resent having a boss, no offense to the nice bosses out there, you just do not believe you were meant to report to anyone but yourself.

8. You want to choose your own business partners rather than being assigned into a project group or team by your management.

9. You feel comfortable with uncertainty of entrepreneurship and with not knowing how much money you might make at the end of the month – this can mean a lot or a little.

10. You hate the politics, hypocrisy and gossip at the work place so much that you prefer your own company to that of others during your working hours.

11. You are self-driven and enthusiastic about your work and do not need to be told what to do.

12. Starting over and failing often do not matter and you won’t mind if your first 100 ideas fail. You will keep trying as you set yourself up for eventual success.

13. You are dying to say “I run my own business” rather than “I work for XYZ Company.”

14. You don’t need validation or approval from a corporation or an organization or a team of management to believe in your own self-worth, talents and skills.

15. Even the greatest boss and the best company in the world cannot give you the fulfillment that comes with working for yourself.

16. Even with a great salary and benefits, you feel extremely limited in achieving financial freedom at corporate because you believe that working for yourself is the only path to creating real wealth.

17. You would rather terrified of taking risks than stay in a job where you don’t take any risks because risks, you say, are the only way to find out your true potential.

18. You find it suffocating to work for a place where your core values do not align to the company’s mission or behavior.

19. You do not believe that you should be tied to your particular field of study or education if your new passions point elsewhere today.

20. You don’t really care what the economy or the government is doing. You know that your future is in your own hands.

21. You realize that some of your family, friends or corporate peeps may not relate to or support you if you pursue this path and you are at peace with that.

If you are interested in learning about the other 79+ questions that I have in store to help you understand whether you are made for self-employment or not, work with me in a coaching session but first, I warn you, it won’t be a warm and fuzzy one. I push you to your edge and challenge you so you put an end your inner conflict and discover your inner courage.

The Meaning of Work

Beware of what work means to you! Cultures and lifestyles have slowly diminished the idea of work to a singular means of a survival, in some cases it is nothing more than a meaningless miserable rat race in which we are “lucky” to partake if we have a “job in this economy.”

Work is not just a means to an end. It is more than about earning a paycheck and making a living. Work can be the sum of your contribution to the world. Work can be your legacy, painted with your gifts and talents. Work can be a direct expression of your passions and that is for more than just the artists, the painter or the musicians. It is for YOU!

Work can be not just meaningful and profitable but extremely satisfying and enjoyable. Work can be the thing you look forward to with baited breath every single day.

My paradigm shift began when I started to see work in this new light, and decided to make it a reality in my daily life.
When will you allow your shift to begin?

If you want uncensored tales of truth on how I went from a top-performing corporate employee to the happiest self-employed woman on God’s green earth, hop on this list below:

  • http://www.ashmenon.com Ash Menon

    That was pretty interesting. I got 9 points, including the minus. I guess that’s not too bad, really.

    • http://www.ProlificLiving.com Farnoosh

      9 points for being self-employed? That’s not too bad at all, Ash. Are you employed by someone else now or deciding / in-between?

      • http://www.ashmenon.com Ash Menon

        Sort of deciding / in-between at the moment. I have a love-hate relationship with my job, so I’ve been at this stage for a few months now.

  • http://www.thedynamicdesigngroup.com Joseph

    Great list of questions! I got 21 points. Good thing I left corporate America a month ago and am running my own show now. I especially love #20 – it kills me to hear people moan about this every day. This is 2012 – go out and create your own work, your own money, your own opportunities!

    • http://www.ProlificLiving.com Farnoosh

      Dear Joseph, a perfect score? Bravo! And good for you to run your own show. Your website looks SMASHING. I love the parting advice. It’s so right on it’s so true and so necessary to say over and over again. Thanks so much for stopping over!

    • Mel

      Love this comment! I felt the same reading #20. Things will NOT be the same when I retire. Why not do what I want to in life and be happy about my choice.

  • http://alwayswellwithin.com Sandra Pawula


    With so much emphasis in the blogosphere on freedom from the cubicle, I think it’s so important for people to feel permission to work in the way that is most suitable for them. Thank you for be so allowing in your post and recognizing that there is no single right way for everyone. I also appreciate the way you highlight the fact that our needs change over time so it’s important to tune into what’s right for us now.

    • http://www.ProlificLiving.com Farnoosh

      Dear Sandra, when I first wrote this post, I had it geared toward entrepreneurship but as you know, I’ve written many posts about the ugly truths of working for oneself and how self-employment is truly not for everyone and so I made this test as neutral as I could to show that, as you said, there is NO single right way for everyone. Indeed! It means so much that you share that here with me. Thank you!

  • http://www.theinternetdream.com Ruth P

    This is a great list! I’ve been self employed for four years and it’s been so HARD, but I wouldn’t have it any other way. I still didn’t answer true to all the questions above, though, but as long as I’m most of the way there I’m happy. I know that self employment is not for everyone, it’s really not easy. Great resource for people starting out!

    • http://www.ProlificLiving.com Farnoosh

      Dear Ruth, you got me curious so I checked out your site and it looks extremely impressive – I mean it. Yes it’s HARD – no kidding, hon. I hear you and I have never worked harder (maybe in electrical engineering school but that was a different kind of hard). What I love hearing is that you just can’t go back. No other way possible. I hear you. Same for me. Thanks for chiming in and I know you’re making a big splash, Ruth!

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  • http://www.byjanet.net/purple Janet

    I definitely feel it’s right for me, 110%! I am simply unemployable now. And I have “no other choice” because I put myself into a situation where what’s available isn’t going to really satisfy me. Living in the Philippines these past 3 yrs, despite having one of the fastest growing economies, means that wages are less than $1,000 a month and average of only $500!! So that wall on a tiny salary that won’t budge is definitely NOT for me. I simply need more for the lifestyle that I want. I DID take a $400/mo job and didn’t even last a month! Yes, I started making more in freelance and I still struggle to hit the $2k/mo mark but I find it laughable that I’ve more than doubled my income of $400 just by doing things on my own terms! 😛

    • http://www.ProlificLiving.com Farnoosh

      Ooooh. Those are some dismal statistics, Janet, but you are way ahead, bravo. It is all in the mind – it starts with what we believe we can do, but of course, a little success along the way goes very long in helping us stay motivated. I’d say that you have had more than that share of success to tell you just how much is possible when you are out on your own and playing by your own rules, Janet, I’m happy for you. Stay with it, and I know you’ll be making a big splash soon!

  • http://williesha.wordpress.com Willi

    I think because I am so excited about starting out on my own (even though I am scared to death) that I got a perfect score. Plus, I have been unsuccessful in the corporate world for as long as I can remember. My biggest fear (which maybe should be my minus) is that I won’t be able to support my new husband, who is wanting to venture on to something else himself. Both of us have dreams of being better, doing better, but only one of us can afford to do it. Since I’m currently unemployed, I feel like I should do it, but I don’t want to deny him of his dream. Perhaps this is a blog post waiting to happen haha. Thank you for this! Tweeting it today.

    • http://www.ProlificLiving.com Farnoosh

      Hi dear Willi, I am excited for you – what a big brave move, congratulations. Don’t worry about not having a big track record in the corporate world because you are about to start yours right now. Sometimes you can take turns pursuing dreams – couples do it all the time – and neither person should have to compromise. You’ll make it work. Thanks for the thoughts and the tweet, Willi, and sending you best wishes…

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  • Katie

    I found a great company that focuses on living a natural and healthy lifestyle. While being able to earn an income staying home with your kids. Take a look at http://pl.momsprovide.com