Are You Cut Out To Be Your Own Boss?

Posted by on Mar 16 2015

I had an interesting discussion with one of my clients recently. She’s been in business for six months and is ready to quit. (I have permission to share her story.)

She writes,

“I give up. Starting a business is so much harder than I thought it would be, so much more time-consuming. I was hoping to be making a profit by now! There are so many things to do and I’m totally overwhelmed. People don’t seem to want to buy my products and I feel totally rejected. I don’t think I have the personality to be self-employed.”

Hmmmm…interesting. Are there really personality traits that separate born-entrepreneurs from people who can’t hack it?

I’d say yes, some personality traits do matter.

I’ve been self-employed in one way or another since 1981. I’ve known many self-employed people, and have been coaching and mentoring them for years. And over the past years, I see a pattern in successful entrepreneurs versus those who pack up and exit their business.

Here’s my must-have list of personality traits for the successfully self-employed (in no particular order):

  1. Tenacity.
  2. Self-worth.
  3. A sense of humor about yourself.
  4. Willingness to do the dirty work (the tasks that you hate to do).
  5. Willingness to learn new skills.
  6. A deep desire to be independent.
  7. Willingness to take acceptable and calculated risk.
  8. An ability to deal well with people.
  9. A passion for what you do or sell.
  10. Resourceful and creative.
  11. Willingness to ask for help.
  12. Self-disciplined.
  13. Self-motivating.
  14. Willing to do the personality “foundational work” to help yourself and your business.

Notice that I didn’t list any business skills here. You can always learn the business skills you need, or hire someone to do the work for you who does have the business skills you lack.

This list is about who you are and what habits you have. Changing your basic personality style will take effort. That’s why #14 is so important: are you willing to do the groundwork, the personality foundational work, to set the stage for your success?

Naturally, there are some personality traits that are business killers, but that’s another blog entry! 🙂

For you, what’s the most important personality trait you have, that helps when you own your own business?


32 comments for now

32 Responses to “Are You Cut Out To Be Your Own Boss?”

  1. Martin Glover

    interesting posting, Karyn, thank you. I am an entrepreneur, in business now for over 7 years and for some reason (or combination of reasons) my business has taken a plummeting downturn. I am finally, for the first time EVER, thinking of throwing in the towel. I am not 100% there yet, but…the notion of a steady paycheck (which I have never had in my life!) is a siren’s song I am longing to hear.

    09 Mar 2006 at 5:47 pm

  2. Karyn Greenstreet

    I know. It’s tough sometimes, and a steady paycheck definitely has its allure.

    16 Mar 2006 at 10:41 pm

  3. Phyllis

    I guess to be funny makes you approachble? Is that what you mean?

    19 Mar 2006 at 6:55 am

  4. Karyn Greenstreet

    While a sense of humor *can* make you approachable, that’s not what I meant. What I meant was a sense of humor can help see you through some stressful and difficult times, and can help make your relationships with your customers and colleagues a joy. And a sense of humor about yourself (and the mistakes you make) help to lighten the atmosphere and keep things in perspective.

    Thanks for asking!


    19 Mar 2006 at 12:49 pm

  5. One of the things that continues to help me is a thirst for learning.

    Nothing I studied in school prepared me for 21st century marketing, and the more I learn, the more I realize how much more I need to learn!

    Every now and again, my brain feels “full.” But somehow, I recover my excitement about learning new information that will help me grow my business.

    30 Nov 2012 at 10:37 pm

  6. Karyn Greenstreet

    Agreed, LaCharla! Lifelong learning for a small biz owner is a must. 🙂

    01 Dec 2012 at 10:16 am

  7. When I read it, I said…
    I too feel that way. I agree with each and every trait. Crisp and to the point. Thanks Karyn. Great comments too!
    Coming to your question.. My answer ..

    1. Not to hold on to the feeling that “self employment” is the ONLY way to go. Just enjoy the process of ups and downs as you will do so in a job.
    2. When I do that, I tend to be more creative and inspired to grow my “Self-employment” without feeling constricted.
    3. NOW it is a whole different relationship between me and my “self-employment”.
    4. This motivates me to become better and better in each of the traits you mentioned and stay in the game ( as of today).

    05 Dec 2012 at 8:23 am

  8. Christine

    Great post Karyn, retweeted it because at this time of year a lot of business people thinking about the next 12 months. I agree with LaCharla, in the current times if you want to earn you definitely need to learn – so many changes in short periods of time.

    05 Dec 2012 at 8:20 am

  9. I have been self-employed since 1991, but I also have thought of throwing in the towel several times. And I sort of did a couple of those times. When my own business didn’t provide enough income I would take on a temporary job (any kind of job) to have a basic income. These lasted from 4 months to 1.5 years… each time I could continue my business on the side and so work myself back to it being able to support me.
    Point is, there is no shame in recognising the reality of your present situation and the need for taking a job AND that that does not mean giving up. It’s only temporary.
    And sometimes building our business a little slower is also okay? Less stress, less pressure…

    05 Dec 2012 at 9:37 am

  10. Hi Karyn,
    Not being one of your clients I feel somewhat like an intruder. So, I do not know your training system. However, being a business owner of thirty years I agree with every attribute you have mentioned. #11 really stands out to me.
    I find that when you ask for help people have a desire to do just that. It may be your consultants or even more so it may be your clients.


    05 Dec 2012 at 9:42 am

  11. Karyn Greenstreet

    Welcome, Harold! My blog is for everyone, so you’re not an intruder, you’re a new friend. 🙂

    05 Dec 2012 at 11:55 am

  12. You have really captured it here, Karyn. Thankfully, this is why I have been able to be successful – and so often people say, ‘I want to be like you’ or ‘I want to be in business like you are.’ And, if they don’t have these attributes, it’s going to be a tough row to how… Thanks for creating this list.

    05 Dec 2012 at 10:07 am

  13. In addition to you list, I’d say persistence, curiosity, self-awareness, adequate coping skills and openness to experience (which is one of the Big 5 personality traits identified in psychological research).

    Building a business is a marathon, not a sprint. We also need to be able to pivot when the market changes. People who need things to be simple, straightforward, clear and never changing will struggle mightily in their own business.

    05 Dec 2012 at 10:08 am

  14. Openness to new experiences and to learning new things is essential.

    In fact, you have this as a bullet point “willingness to learn more things”, but I think being open is so important it deserves extra mention. It has always been so important for me to have an open-mind about how to do things (new ways to market, etc).

    I find many business owners, for the exact reasons they got in business (to be their own boss and independant) resist making positive changes that could positively impact their business (i.e. the mindset of “that doesn’t apply to me or my business”) when it really could quite profoundly.

    So I find the really successful ones are those who are open to life in a multitude of ways and open to having a beginner’s mind and in knowing that you won’t always be the expert in every way and that’s ok.

    05 Dec 2012 at 2:47 pm

  15. I love this list Karyn! I really, really dislike when I hear someone “recruiting” someone by saying “Anyone can do this”. Being self employed which I have been on and off for over 20 years is both rewarding, and challenging, and certainly not for everyone!

    05 Dec 2012 at 2:54 pm

  16. Like you I have been self employed in several ways since 1981 sometimes successful (by others’ standards). I had a stroke in 2005 which has left me speaking “funny”, with a spastic right hand and poor balance. When I was talking with a friend (who’s never been self employed) about what I could do , she said et a job. I looked at her said that wasn’t an option because I’ve been self employed more of my life than not and I definitely didn’t know how to work for anyone other than me !

    I’ve already got a website and coaching biz but recently bought the domain name I plan to teach them how to start their own biz because they have and use all the characteristics you’ve listed above – EVERY DAY just to live 🙂

    05 Dec 2012 at 3:19 pm

  17. Timing is everything! I had this conversation about an hour ago in the parking lot at a client’s site.

    Number 9 means more to me than the others. I love what I do and I do it well. This journey has lasted more than twenty years. I sometimes do my work for free when a client is having trouble and I know I can help. The money finds its way later.

    Thank you for a great list. I’ll forward it.

    05 Dec 2012 at 3:23 pm

  18. Craig Mulgrum

    Right on, Karen!!!

    If you don’t get out there and have the stamina to keep going, both mentally and financially then it’s curtains.


    05 Dec 2012 at 3:48 pm

  19. Thanks Karen, I love reading this list and a few of the extras – like ‘openness to experience.’
    It feels empowering to read !
    While not strictly a personality trait I’d add ‘be a thinker’ to the list.
    Solutions, fresh ideas, resolutions – all require great thinking to forge new pathways to fabulous places.

    05 Dec 2012 at 3:50 pm

  20. leslie

    agree…Tenacity would be my #1 – taking a deep breath and digging in your heels 🙂

    Sadly too many expect instant success and never think about all the ‘work’ involved – the business side of the business.

    Re-evealuating and restructuring has also been key for many in this economy – as you well know, being you addressed that a while ago.

    Also the ability to ignore (limit or cut) the negative people around you – those that say “why don’t you just get a real job.” If your well-meaning family or friends don’t get, best to keep that part of your life separate and out of conversations…Surround yourself with positive and good things will come…in time…

    05 Dec 2012 at 4:55 pm

  21. One trait that has been a lifesaver (uhm, I guess it’s a skill, it took me a long time to start getting the hang of it) is the ability to put the good of my business ahead of my ego. This makes me lots more flexible, able to re-invent, make shifts, and yes, now and then take a 3-month contract to keep the bank balance afloat while I change whatever needs changing to get back on track.

    A secondary advantage to taking a temporary (part time if at all possible!!) job is that it removes me from the business grind perspective for a bit and helps me to think about necessary changes within bigger contexts. Thank you for your words of wisdom.

    05 Dec 2012 at 6:06 pm

  22. I would have to add honesty to the list. You have to be honest enough to say you don’t know if you don’t.. and honest enough to say you screwed up if you did 🙂 People appreciate honesty, and if they don’t, well you probably don’t want to do business with then anyway.

    05 Dec 2012 at 8:28 pm

  23. Cheryll

    My most important personality trait? Persistent belief in my capacity to succeed, especially when business plans are going off course.

    28 Dec 2012 at 2:27 am

  24. Karyn Greenstreet

    I love that one, Cheryll!

    28 Dec 2012 at 5:18 pm

  25. This list is reassuring for me. I’ve been freelancing for 3 years now and I continue to see the realization of me one day being self employed on a full time basis. I’ve had great months were I sit home or in a coffee shop and make enough to pay all of my bills. Other months, not so much. I need to crack the code, because I am born to work for myself as I am an A+ customer service giver, I immediately disarm people from ALL walks of life with what I’ve been told is charm, and I’m good (on my way to great) at what I do. Talk to me Karyn….

    01 Jan 2013 at 12:14 pm

  26. Karyn Greenstreet

    Hi, Dion,

    Yes, personality traits DO matter when it comes to being a successfully self-employed small business owner. Of course, so does your marketing, your audience, their needs and what you offer them. A business model contains multiple pieces of the puzzle, so if there are some months when you don’t make your revenue goals, you need to look at your entire business model to figure which piece (or pieces) of the puzzle isn’t working.


    01 Jan 2013 at 7:52 pm

  27. Susan

    Hello Karen,

    Great post Karen, thank you. It’s very thought provoking.

    I have found one of the most important things for me was to be prepared to step (jump) outside my comfort zone (constantly). If I didn’t, I wouldn’t have ever got my business off the ground, let alone grow it.


    11 Apr 2013 at 5:59 am

  28. Budi Prakoso

    Thanks, Karyn.

    I just started doing reselling thing a couple of weeks ago and hope that this would be my start of setting up my own business sometime soon. 🙂
    Your ‘are you cut out to be your own boss’ article is surely something I need to bookmark on my laptop coz I might lose track along the way and yours would be some sort of compass of which direction I should take and re-energize myself.
    Thank you so much. Glad I clicked your feed in my gmail. 😀

    24 Mar 2015 at 10:10 pm

  29. Karyn Greenstreet

    I’m glad the article inspired you, Budi! (And I’m glad you clicked my email in your Gmail, too!) 🙂

    25 Mar 2015 at 9:58 am

  30. Very useful question Karyn. Thanks for raising it.

    #1. Tenacity and Willing to do the personality “foundational work” to help yourself and your business are the game changers in my view.

    I have shared this post with the virtual alumni job club I administer and on twitter. Having a good heart-to-heart with self on this is so important. Any foundation item we ignore today, is bound to sabotage us tomorrow.

    Thanks again!

    25 Mar 2015 at 11:34 am

  31. Karyn Greenstreet

    That’s so true, Cheryll! Whether you’re newly self-employed, or have been a small business owner for 30 years, if you don’t work on your foundation, it will come back to haunt you.

    25 Mar 2015 at 2:41 pm

  32. […] Make sure you have the personality to be self employed (more on that here in my post “Are You Cut Out To Be Your Own Boss?”). […]

    07 Feb 2018 at 1:28 pm

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