You Should Be Careful

You Should Be Careful post image

People often say to others who are making big changes to “be careful.” Sometimes they’ll follow up with something casual like: “you might mess up your career.”


Last week, when I was being told again to “be careful” in a situation in which it seemed completely irrelevant, I got to thinking: What would being careful even mean right now? Probably shutting up and doing nothing.

What is she really trying to say to me? 

Unless the person urging you to be careful is being precise (e.g., when you install Windows 7, be careful to backup your old files) 9 times out of 10 “be careful” just looks like advice.

It’s a buzzkill, a downer– a show of no-confidence. In some situations, it’s a dream-zapper.

(Them) “55 in the fast lane”: “What are you gonna do about that new company you’ve been talking about?” 

(You) “Action Jackson”: “I’m going to quit my job next week and finally focus full time on my start-up. I can’t freakin’ wait!” 

(Them): “You should be careful…” 


9 times out of 10 translation: “I’m not really entirely clear on what you are up to, so I think you should weight your options before you do anything rash. In the meantime,  I’ll continue to be worried and or skeptical.”

By the way– the “meantime” ends when you start making money. Or get on Oprah. Both are pretty tough.

*  *  *

As I try to think back at the times people have told me to be careful with no precision, it’s almost 100% from the good of their hearts. They really care. They don’t want me to get into trouble, to sound like an idiot, or to do something I’ll regret. (By the way– too late, too late, and too late.)

When I explained my big plans to quit my job and start my own business, the #1 piece of advice I got was: be careful about that, you shouldn’t do it yet. 

Be careful not to screw up everything you’ve worked for.

Be careful not to go down a path that would ruin your retirement.

Be careful not to anger your current employer.

*  *  *

It’s our most fragile ambitions and dreams that are attacked by “be careful.” Most of the time we bring it on to ourselves.

I’ve noticed the amount of “be carefuls” I receive are directly related to the amount of permission seeking I’m doing. If you know that people will be threatended or unsettled by your projects, don’t talk about them. Pros don’t ask for permission.

Of course, I’m not a pro yet. I’m a blabber mouth.

So I say to myself: stop talking about your start-up. Your book. Your big ideas about the future of that one thing. Your friends are just saying “I care about you.” And you’ve given them a chance to show it.

You want to build businesses? Write books? Tour the US playing rock music?

Go ahead.

Nobody is waiting.

It’s just you.

For a while.

My be careful list:

You need to be careful that…

  • you try to create your best work.
  • you go deep on your most important projects.
  • you don’t miss the opportunity.
  • you don’t shy away from difficult decisions.
  • you don’t waste your life.
  • you appreciate things.
  • you don’t let your immediate emotions highjack your life and work.
  • you have fun and play.
  • you have the confidence to do what you want, not what others think you should do.
  • you don’t self-destruct. That you don’t become your own impediment to success.
  • you don’t offload responsibility for your opinions and actions to others.
  • you don’t cultivate blind spots about your personality and capabilities.
  • you never become jealous or hateful of others around you.
  • you never keep tabs for the gifts you give.
  • you don’t complain too much.
  • you don’t talk to much.

Full of care.

My grandma used to have to the serenity prayer posted in her garage. I always thought it was cool. Here it is re-written for entrepreneurs:

God, grant me the serenity to accept the misgivings of those with inappropriate experience or perspective

The courage and sensitivity to identify the useful concerns (that are morally compelling)

And the wisdom to know the difference 

(Also, while you’re at it please consider delivering on to me the undying stamina to make it happen). 




PS, would have preferred a better blog post? No problem! Here ya go:

Published on 04.27.12
  • Dude…. you are on FIRE! In my opinion, 99% (or 99.99%?) of blogs suck. They are generic, boring and provide nothing unique.But yours rocks. Your writing is steadily getting better and better. The way you’re expressing your ideas is killer. The compelling ideas just keep coming. 

  • Agreed with John, you’re writing is getting better and better, deep (and relevant) shit, loving it!

  • I hear this all the time.

    Fortunately it’s only my dear old mum and she means well, but she puts the old in “old skool.”

    It used to get on my nerves, but not now. If I hear it from anyone else I just don’t explain.

  • Frank Bonetti

    You sir are a gentleman and a scholar.

    I love these types of inspirational posts. It’s always nice to have a little affirmation from time to time I’m not alone in this and that I’m doing the right thing. I feel like I’ve grown and matured immensely since I started reading all of these entrepreneurship blogs a year ago. If someone had said to me “be careful” a year ago, I probably would shrugged and said “okay…”. But now when people give me this sort of unsolicited, well-meaning “advice”, I don’t even give it thought. I just keep moving forward.

  • Yeah, quality posts keep increasing. Don’t stop writing. Thanks for the post.

    I’ve stopped talking about what I’m doing with some people.

    Any “be careful” advice tells me more about the person giving it than if what I’m doing is right or wrong. They’re responding based on their lives and how they’re feeling about something – not your life and how you’re feeling about something.


    An always-on full engagement mindset for me leads to your points dan, every single one of them.
    Sometimes it even helps to go a little animalistic when you need to make serious shit happen.

  • Great post Dan.

    Ask for forgiveness, not permission.If you ask in the beginning for permission to get started – the amount of “be carefuls” can stop you dead in your tracks. But once your plans are already in motion, people are a lot less likely to get in your way. And once you start seeing success the “be carefuls” all but disappear.

  • This one was a heart-warmer ;-) I agree with everyone else, you’re really blossoming as an author AND it’s super nice to feel understood. I too just give very brief summaries (if at all) to avoid getting that predictable perplexed look. I’ve come to the conclusion that for most people my success is based on how much they think I make. Sort of a pity, but it just makes me that much more determined to do something significant with my life.  

  • Bec at Dreamline Diary

    I can’t speak for anyone else, but I have no idea if my business I am working on will or won’t be worth the time I am putting into it. I have supporters to whom I say thank you. And I have those saying “be careful” or “stop wasting your time, no one buys anything any more”. The noise is deafening. That includes the noise in my own head. All I can do is my best. Make the best product I can and follow my dreams.

    Dan, your posts are great. I always look forward to receiving and absorbing the information you so kindly share. I wish you the best for your business ventures. Follow your dreams.

  • Very interesting perspective. I’ve never thought about that before, but you are completely right. “Be careful,” without any specificity, isn’t really advice, it’s just skepticism. They might mean well, but that doesn’t mean they are right. Great post.

  • Dan

    Thanks Johan, appreciate the support. I like the idea of the types of comments that reveal more about the person delivering them than the topic at hand. I feel like I still suck at figuring that stuff out. 

  • Dan

    Haha, thanks Frank. Probably more a scholar than a gentleman, and wow you’ve seen my writing!!! :D

  • Dan

    Thanks Michael.

  • Dan

    Cheers Bec, that’s such an interesting topic you bring up. “how to know”… one way is to do stuff you are pumped about anyway, but that’s easier said in motivational books than in the real world. best of luck with the biz. 

  • Dan

    haha thanks :) yeah the further thing that sucks (as if we need more) is that if you don’t ever turn a buck, they’ll likely never take the effort to take a look at what you did and why it was important to you. oh well, i suppose world’s smallest violin kind of stuff. we are lucky to have such lovely problems :)

  • Dan

    agreed sir :)

  • Dan

    haha weird word but i totally know what you mean by getting animalistic and just absolutely powering through stuff. 

  • Dan

    thanks Liz! 

  • Dan

    Appreciate all your support John!!! I’ll keep cranking

  • Dan

    word. My mom used to rock this one all time, all with the best intentions. now i think she must listen to the podcast occasionally! :D mom, are you here? 

  •  Tis true! Even our worst problems don’t compare to many parts of the world. I hear ya on the violin ;-)

  • I am the same Blabber Mouth. It is generally because I am so excited about what I am doing, I am S-U-R-E everyone else will be as excited. But I have also learned, to temper the excitement, post it on a forum or the DC, those are the people who can say, go for it, (they have no dog in the race, they are excellent cheerleaders). It is out of permission seeking, or affirmation of my decision, but it usually turns into something …be careful….and so yes, why seek permission when having a secret is just this wonderful naughty special feeling LOL….

  • Dan

    haha…. i can 100% relate :)

  • This post had me laughing out loud. I get the impression you were a bit angry Dan when you wrote this and that you’d had enough of hearing it!

    I think this “be careful” thing people give you is a form of negativity. When I hear that kind of thing it spells mediocrity from the person saying it.

    They just don’t get what you’re doing. It means that they just find it way outside their own frame of reference or understanding of the world. So all they can offer is a “be careful!”.

    Enjoy reading TMBA – and LBP. Great material.

    Whatever you do though – Be Careful!

  • Dan

    Haha guilty! Thanks for checkin’ it out Kevin :)

Next post: