How Oprah Winfrey Helped Me Trust My New Hopes More Than My Old Habits

It was about 10 years ago.

I bought a ticket to see Oprah Winfrey on one of her summer “Live Your Best Life” tours. I drove 5 hours to Raleigh, NC. I sat with people I didn’t know because none of my friends wanted to go with me.

I listened to Oprah’s 2-hour opening speech in awe. I spent the day going through the journal she gave to the participants – as she encouraged us to face our own “stuff” and get clear about our lives. I answered every single item honestly and with as much vision as I could muster.

I drove back home on a “Hope High” that I thought would never go away.

I’m sure you know what happened.

About, oh, 3 hours into the very next day, I was face to face with “reality.” My old thought habits came back to crush my new Hope High. I was face to face with my life, my money problems, and all the “stuff” my current mindsets had created for me. (Where was Oprah when I really needed her?)

The cynical among us would have us believe that my day with Oprah (or your day in a similar situation) was bullsh*t. That I was only momentarily distracted from the practical reality of my life. Disillusioned. Duped. Dumb.

Here’s the thing though:

I recently found that old journal that Oprah gave me 10 years ago. Everything (everything!) I wrote in there has come to pass. And during these 10 years, I’ve gone to other cool events, read uplifting books, and talked face to face with people who inspired me to no end. Again and again, I’ve gotten lost in the pure potential of possibility. And of course – I’ve had the old crummy thought habits come up the very next day trying to convince me that the possibilities I saw for myself were just pipe dreams.

But I’ve come to see the pipe dream (and the hope high differently) now. After spending that day with Oprah, I began to ask myself one very un-cynical question that changed it all:

What if that HOPE, that HIGH, that inspiration I felt was the TRUTH? What if that was the REAL ME – and all this other icky stuff is the BS?

Think about it. From the day we’re born, we’re taught that the cynicism and doubt are “smart.” We use them as a protective shield. We ward off the hope, the dream – and we successfully keep ourselves stuck.

Still, we get these amazing glimpses of ourselves, of what’s possible.  We also get these fantastic ideas and opportunities. We see our greatness as if it’s standing right in front of us. Sometimes other people or big events help us see it. Sometimes it’s a book.  Sometimes it’s just a moment of pure living in the present moment.

If you’re like most people (and me),  it’s easy to crush that hope the minute the voices of “reality” set in.

It is imperative that you learn to trust that hope.  Here are five things I’ve learned since that day with Oprah. They are true even now as I keep on expanding and changing into even bigger dreams. Let them guide you through the new hopes AND the old habits!

1 – It’s much easier to stop trying than it is to keep believing.

It’s so easy to just believe the old habit voices that whine criticize and shame. Why? Well – let’s be honest – cuz then we don’t have to DO anything!

2 – The Pipe Dream and the Hope are part of the process. But so is the tedium and the work.

Without the dream, you’d never get started. Without the work, you’ll never get anywhere. (And yes, the work is sometimes slow, boring, clean-up work.)

3 – Expecting to feel inspired and happy 100% of the time is the real pipe dream.

I’m a huge believer in Martha Beck’s “shackles on/shackles off” approach. Also – in the Abraham-Hicks “feel good” philosophy.

AND, in my own experience, much of what I thought was a “shackles on/doesn’t feel good” experience – was my assumption about that experience. In fact, sometimes just getting something done or being proud of myself was the “feel good” I was looking for! When I expect inspiration and happiness to constantly be there before I do anything, then I set myself up for staying stuck.

4 – There’s a connection between discomfort and happiness.

We imagine that true happiness is hanging out by a pool sipping froo-froo drinks.  While that can indeed be fun – it will eventually get boring.  Our souls have more in mind for us than froo-froo drinks. Our souls have more in mind for us than protecting us from failure.  Time and time again, I’ve helped my clients move out of the stuck place into deep places of discomfort (and then success).  One of them recently put it this way: “This is the most uncomfortable I’ve been in a long time – but I am so happy and alive! It’s way better than being stuck!”

5 – Make time for more hope.

Feed your hope. Feed your vision. Read books that inspire. Hang out with people who believe in you.  Make time in each day to tap back into that place of hope and vision.  This will act as navigation and keep you moving in the right direction.