You Should Be Careful

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: