Would you have done this? One of my über-uncomfortable (but proud) moments

I want to tell you about a time I made a lot of powerful, wealthy people very uncomfortable.

I was at a dinner – a very fancy dinner. My boyfriend at the time had just received a job offer with a highly reputable group after a competitive interview process. This was where we were going to all come together and they were going to meet me, and we could all hang out jovially and celebrate.

Things were going well. Despite growing up poor and with dinnertime around the TV set, by the time I was at this dinner I’d had a decade+ of practicing learning what to do with all those forks and spoons and how to make polite conversation with total strangers. There were many people at a very loooong table, and I was entertaining everyone in my vicinity.

I was in the middle of a story about an avalanche in the Himalayas.

But then the “thing” happened.

In the background, I picked up something in a conversation that I wasn’t a part of, and someone said, “What are black people complaining about anyway? Slavery ended over 200 years ago. It’s not our fault anymore. It’s time to get over it.”

I stopped mid-sentence with the person I was chatting with. I turned around and said, 

“I’m sorry – what was that?”

“Oh, I was just saying I didn’t know why black people are still blaming slavery for all their issues when it ended 200 years ago, you know?” He was smiling. He was expecting me to smile back and agree.

There was an uncomfortable silence, but also an air that this discomfort would quickly go away once I realized “he wasn’t being racist.”

Except that’s not what was happening.

I turned my chair to face him fully. I picked up my glass of wine and took a large swig.

“Actually, segregation only ended in 1964…legally. That’s less than 40 years ago” (at the time).

I took another sip of my wine along with a deep breath, smiled, and waited for a response. Nothing – except for the smile turning into a very serious face, and awkward silence from the entire table, with a few uncomfortable laughs attempting to lighten the situation.

I continued, “Also, institutionalized racism and de facto segregation is still happening. 

Like in hiring practices, school segregation and residential segregation due to things like ‘white flight’ among other issues. So you see, it’s all very real and it’s totally happing right now.

So actually, why people are still blaming rich white men makes sense to me. But I can get how that might feel uncomfortable to think about.”

I smiled and shot him a welcoming vibe – like, “Here’s your chance. Open up and learn something new, dude. Admit what you said was not ok. Evolve, dammit.”

I tried not to seem angry. But I was confident, knowledgable, and carried myself such that it was clear that I’d take on any kind of arguments with grace. Maybe not as much grace as the notorious RBG would have, but at least my own version.

I’ve learned many people don’t open up their minds when they feel attacked. I’m not saying there isn’t a place for outright flame throwing. I’ve been there and done that when it makes a difference. But I’ve learned over the years that many people are more wiling to listen when they aren’t feeling under fire. When we open with giving them the benefit of the doubt.

And while impact matters more than intent, so many people are not trying to be assholes. So I try to educate – before throwing flames.

He took a deep breath.

“Well, Ana…thank you for letting me know. I didn’t think about that part. It’s always nice to learn something new. I’m sorry if that offended you.”

How polite. How…uneventful. How…lacking in curiosity about how to evolve.

I replied, “I understand. It can be hard to remember that it’s the ‘land of the free’ for only a select few, especially when you are the one with the all freedom. But hopefully it’ll be easier to remember now. I know you’re a good guy and will do the right thing.”

I don’t know if he shifted his actual beliefs as a result of what I said – or if he even meant what he said – but I do know that at least I could sleep better that night. I acted with integrity. I also gave another human the benefit of the doubt. I was in alignment with my values, inside and out.

No regrets.

I hate regret. It’s a shitty emotion.

It’s one of the reasons why I do the work I do – so that people can live a life without regrets. And living a life without regret takes confidence. Courage. Vulnerability. Compassion. Self-compassion. Risks. Failures. Empathy. Loving humans…all of that does not come easily.

Living a life without regret takes practice, skills, commitment.

Partners in crime are also helpful.

Which brings me to my boyfriend. I could tell he was uncomfortable, but that he knew I was doing the right thing. I could tell he wished I hadn’t said that – but that he knew it was the right thing. I knew he was proud, but also embarrassed at the same time. I knew he wished I hadn’t said anything, but that wishing that was wrong.

But I knew that he really, really, really kinda wished I didn’t say anything – and that he was hoping I wouldn’t do it again.

I knew then he wasn’t my Person.

Alignment. Inside and out.

Who are you willing to disappoint so you can honor your truth?

Suggestion: anyone.

If you want to work on living a life without regrets but don’t know where to start, schedule a free strategy session with me.

I don’t offer these all the time, so snag it while it’s hot. Click here to grab your spot. It’s probably the single best use of 30 minutes you can come up with anytime soon. Pinky promise.

To Your Freedom!


If you want to join a tribe of people that will help you navigate this wild and precious life, come check out Freedom School – for rebels like you. It’s not just personal growth for rebels. It’s Jedi training for the new world.