The Price of Regret

Pssst did you know you can highlight any sentence to automatically tweet it? Give it a try!

* This is a guest post by the brilliant Leah of I know this one was hard for her to write. The regret of not pursuing her dream is still very palpable and holds a strong emotional charge for her to this day. Powerful stuff!

You’re here at The Uncaged Life because you want to live a little more extraordinarily. You’ve got big dreams to travel, to create art, to build businesses, to start a movement, or to make something amazing happen.  You’re in the process of building your dream life, and that freakin’ rocks.

But you’re still a little…stuck.

There’s something holding you back, and you can’t put your finger on it.

So instead of waiting just a little bit longer for whatever inspiration you need to live your dreams, allow me jolt you to action now.

It really boils down to this:

what is the price of regret?

That’s a pretty intense gut check, right?

Look back to any regret you have. Maybe you didn’t go on a study abroad in college because you didn’t want to part with your significant other. Maybe you didn’t tell that special someone how you felt. Maybe you decided to take the “responsible” career instead of the “artsy” one. It could be anything.

Now ask yourself the following questions:

  1. What would you pay to go back and do what you really wanted to do? Truly, put a dollar amount on it.
  2. Looking back, would you take the financial risk of pursuing a dream?
  3. Looking back, would you be willing to sacrifice the time?
  4. How much time are you spending now *waiting* for your dream to happen to you?
  5. What is the value of your time?

I’ll give you an example of a regret that really stings at my heart.

After college, I had the chance to pursue a job in Austria with an international government agency. It was everything I wanted at the time, but I was really getting in my own way. It would be very expensive to travel and live there, I’d be leaving everything I knew behind, and I had to stay for a minimum of three years.

Staring that situation in the face at 22 years old, I was terrified.


I knew I wanted this international dream job, but yet, I gave myself 9,000 reasons not to go YET.


Most of all, I told myself I needed more money.

I took another job in the States to make some money while I sorted out how I’d afford to pursue my dream job. In my head, it was a means to an end.

Soon enough, I was offered a great salary in a “safe” corporate job, I lost the skills that would qualify me for the dream career in Austria, and I lost the contacts who would be my references. Soon enough, the dream job in Austria was filled by another person.


Slowly but surely, the chance of pursuing my dream died.


Knowing what I know now, I would pay thousands of dollars to have that opportunity again. I would risk my 22 year old life’s savings to travel and live in Austria. I would give 3 full years on the job and then some. My short time on the planet is priceless, and the waiting I did cost me regret.

Don’t let this happen to you.


What if you knew right now that the dream you’re harboring would become a regret? How much would you pay to prevent that from happening?


Now, how much is a coaching session? A plane ticket? A business program?

Thaaaat’s what I thought.

Now that the Austria path has closed, I’m working my way toward a new dream: entrepreneurship. And there’s no way I’m letting this one slip away!

The final word: Run headlong for your dreams, and don’t let money stop you. It will cost you mightily in regret if you don’t do it now!


What is the price of your regret? Is there something in your life you desperately want to do, but you’re holding yourself back? If you don’t do it, what’s the cost? Tell us in the comments!

© Sarah Osbourne 2012, Sarahkosbourne@gmail.comLeah Manderson helps people afford their dream lives. To learn how to set up a system to help you afford your dreams on autopilot, sign up for her 7-day mini program at



Read 1 Comment & Leave Yours

  1. leahmanderson

    Thanks so much for posting this, Rebecca! Happy Birthday to you, and keep inspiring people to live their dreams :) :)