Are You Cut Out For Having Your Own Uncaged Career?

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I work with a lot of people who have BIG dreams of quitting jobs, travelling the world, starting a small business, and living a life of freedom and adventure. And I’ve spent a lot of time analyzing people who are actually able to make this kind of lifestyle work (because let’s face it, not EVERYBODY is cut out for this).

It sounds like a nice idea to be sipping mojitos on the beach while writing your latest blog post, but it takes a certain special type of person to actually make it work for the longterm. The no bullshit truth is that a lot of people who want this lifestyle don’t have what it takes. That’s not a judgement or a belittlement – it’s just a fact. Kind of like how I’m not cut out for a high end corporate job. It’s just not my thing. Neither is better or worse.

So if you’re thinking about entrepreneurship, there are some things you should know about what it takes.

Here are the top 10 qualities I see that most (/every?) Uncaged entrepreneur has:

1. They are freedom-seekers

Above anything else.  And freedom can mean a bunch of different things – it would mean time to travel, working on your own schedule, having time for your family and kids, working on what you want when you want. But this has to be the driving force in your life to make this kind of lifestyle work. When freedom is at the top of your values list, you do what needs to be done to get it – you don’t let the mundane tasks or the (things like learning about how to manage your emailing list, and worrying about finding the perfect idea), get in your way. Freedom Seekers know that lifestyle is the most important thing, and they don’t get bogged down with making every last decision so precious, rather, they do whatever it takes to get the freedom that they want.

2. They are flexible

People who actually make entrepreneurship work know that things don’t always go as planned, and they are ready and willing to change things up at the drop of a hat. They understand that the best way to do things is through trial and error, and they are able to go with the flow… even when they really, really wanted the flow to go a different way!

3. They trust

Themselves… Others… The universe. Even when they have no idea how the hell they are going to get there, they KNOW that they will. It’s not about being super cocky or arrogant, or using the law of attraction or any of that nonsense – it’s about having a deep sense of trust that things will work out for them. This means they also trust themselves to make decisions, to know what they want, and to believe that it will all work out.

4. They know how to ask for help

No one can do this alone, and those with Uncaged Careers know that not only does asking for help NOT make them look weak, it gives them an advantage. They know that they don’t need to re-invent the wheel, and asking for help is a short-cut to making things happen faster. They’re able to let go of their egos and learn to collaborate, seek guidance, pay for help, and not try to lone-wolf it.

5. They don’t like other people’s rules and they’re willing to go against the grain so they don’t have to live  by them

Not all, but most people who have Uncaged Careers have some element of rebelliousness to them. They think outside the box, they don’t believe things at face value, they question what life “should” look like, and they’re not too worried about standing out from the crowd. Actually, they usually do what they can to make sure they stand out from the crowd. And all the people that tell them they’re crazy and that they’re being unrealistic (which is usually their family, friends, and past-life co-workers) – they have the courage to tell them “Actually, spending the rest of my life in a cubicle feels unrealistic to me, so shut up and let me do my thing”. To follow your Uncaged Career dreams, you really have to be willing to step away from the masses and be ok with knowing that some people think you are crazy (which comes back to #3 – trusting yourself enough to know that you’re not crazy).

6. They are extremely self-aware and always trying to learn more about themselves

They are constantly analyzing why something worked for them, why it didn’t work, and making changes as they go. They understand that in order to not burn out or get bored, they have to be super honest about what they want. They know the little intricacies of what makes them happy and all the things that piss them off, and they use these to structure their business and their workdays. And when something goes wrong, instead of getting mad and giving up, they use it as an opportunity to learn more about themselves.

7. They are comfortable with some level of risk

It’s not that they are huge adrenaline junkies that can’t seem to stop moving, that are willing to make snap decisions based on no evidence. No no no… That kind of attitude would be hard to build a sustainable business around. But they ARE willing to do things without knowing the outcome. They are comfortable with a medium level of risk. They are willing to start before they are ready. They understand that uncertainty is a cornerstone of life and instead of fighting against it, they learn to use it to their advantage – instead of stressing and worrying about outcomes, they launch sooner, knowing that if they sit back and wait til everything is perfect, they won’t get anywhere. This, obviously, means they get results faster.

8.  They’re willing to admit their mistakes

They know that the quicker they can apologize and move on, the better. That is to say – they don’t get hung up on the blame game, on having to be right, on being narcissistic little jerks who think the world revolves around them. They know when to hold ’em and when to fold ’em. If they fuck up bigtime, they apologize and make it right, because they understand that their business has a reputation that goes beyond their ego.

9. They are unwilling to settle

Sure, they might settle down. But they never, ever settle. For jobs that suck, clients they’re not thrilled with, work that doesn’t light them up. They refuse to accept a life that is mediocre. They’re idealists, and they really do believe that they can have everything they want (again – see #3). And because of this, they’re always looking for the next idea, the next adventure, the next new project. It’s an ongoing process and it never really ends.

10. They are willing to fail

A lot. And keep on going. They’re willing to be wrong, to make mistakes, and to put stuff out there and have NO ONE bite, and move right on to planning their next thing. They launch their course, and no one shows up. And instead of quitting, they slap a “sold out” sign on their website, make some changes, raise the price, and try again. They majorly miss an important deadline. Instead of holing up in embarrassment, they do what they need to do to make it right, and they move on. They have clients that fire them because they’re not happy with their work. And instead of running the other way, they apologize, get feedback, make tweaks, and learn from it so they can do better the next time. They totally love when things flop because they get to learn what doesn’t work, which gets them one step closer to learning what DOES work.

So, what if the above does not describe you? Then I’d ask yourself what it is that you’re wanting from entrepreneurship? Freedom? Lifestyle? More time? Well you don’t need to change your whole job just to get those things. Build more of what you want into your lifestyle NOW, and you might find that your Uncaged life is closer than you think.

And if you DO see yourself in a lot of the above qualities – bring it on!

What do you think? Are you an entrepreneur who sees yourself in these categories? Which one resonates the most with you? Comment below.

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Read 14 Comments & Leave Yours

  1. YEP, this is me :).
    P.S. Totally borrowing this if this happens on my next program:

    They launch their course, and no one shows up. And instead of quitting, they slap a “sold out” sign on their website, make some changes, raise the price, and try again.

  2. Totally resonates with me.. Sometimes I think I’m weird for being this way but guess am not! In fact, I’m SO amped about learning about myself that post B-School, I’m joining Leonie’s Amazing Biz+Life Academy to really up my game.. Loved your post and look forward to connecting!

  3. CindyEyler

    This is a GREAT post!!  You hit the nail on the head, and it is all absolutely true.  I agree is takes this kind of a person for it to work, so those that sit around whining and not willing to do what it takes… well… what can I say!

  4. This totally resonated with me. I am a freedom seeker and it’s most definitely my highest value.

  5. Miss Sassy Yes! Seems to be a common one for us entrepreneurs. Freedom can mean different things for everyone, but I think what a lot of us are after if the lifestyle we want, and we will do anything to get it.

  6. CindyEyler Thanks Cindy! There are LOTS of different kinds of people who could be entrepreneurs, but I find that the ones who really hustle it with online business have some element of each of these traits.

  7. Prerna Malik congrats! enjoy the course

  8. Sabrina at MyMiBoSo doooo it. It works ;)

  9. angieandriot

    Love these! Being self-aware and willing to fail seem like the foundation of being an entrepreneur. If you don’t know who you are, you’ll have a hard time building a business that is right for you – and attracting customers that are right for your business. And if you’re not willing to fail, then you’ll be forever stuck in the land of adequacy, where you never push yourself to your full potential!

  10. SheRadiantCoach

    Perfectly said Becca. It is such a reality. It is so easy to start a “lifestyle Biz”, but it is a whole different thing to actually stick with it until it works. There are days when I want to crawl into bed and shut it all out and give up, but then I keep on going, I’m flexible and I trust that it will all work out! Thanks for holding the candle up to the truth of how challenging (and yet rewarding) this work can be. 

    Keep rockin it sister!

  11. ahacatalyst

    Thanks for sharing these 10 qualities with us. I recently read Tim Ferriss’ “The 4-Hour Work Week” and I got to say I was intrigued by this concept of having a lifestyle biz. And from reading that book and being introduced to the concept and then reading your post, I agree. Not everyone is ready for this type of adventure. Sometimes it is because of who you are as a person and sometimes it is where you are in life. It is a romantic concept–but you have to be true to yourself and what you ultimately need and want in life. Reading about these qualities helped me understand what mindsets you really need to be at that stage to launch. It really does require you to let go of things that are safe and easy to really LIVE life and go where it leads you. Lots to think about!

  12. KarenYank

    Such great stuff!  I love that you mention the ability to admit mistakes, I find that’s a biggie!  I missed an appointment today that I simply didn’t get on the calendar, and just offered an apology.  A mistake, I admitted it, we moved on.  :-)

  13. KarenYank love it! no excuses! “i messed up.. i’m sorry… how can i make it better?” easy and WAY more productive than trying to justify!

  14. Beautifully articulated.  
    I am strongly connected to all of these qualities but the one I need to consciously focus on in order to grow my business to the next level is #4. KNOWING HOW TO ASK FOR HELP I enjoy being a Jane of all Trades and switching hats from creative design to health coach to marketing director. I love collaborating but I need to work more on letting people just do things for me.– Asking for help and releasing the outcome into their hands. Wait… did I just admit I’m controlling when it comes to my vision for the company?