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A Story Of Personal Connection ( & Another Reason Why Having A Business Is Awesome)

I didn’t share this story when I first got back from my recent round the world trip because first, I wanted to see what would happen, and second because it felt (and feels) very personal.

I am sure there will be people who disagree with what I did and think it should have been handled differently. When I feel a connection though, I like to go with my heart.

During my recent trip to New York (here’s all other business-related stuff I did if you want to check that out as well) I made connection that was super meaningful to me and I hope this relationship will grow and develop over many years.

I spent a lot of time in the city with high-level entrepreneurs, which of course was amazing fun. I love hanging out with people who are kicking goals and making things happen in the world.

But one of the connections that meant the most to me was making friends with a homeless woman.

Here’s how it happened

I was on my way to buy a dress for an upcoming VIP party (hello potential cultural divide!) and I saw a girl sitting on a blanket reading with her dog. Clearly she was living on the streets.

I must have seen at least fifty other people on the street by this time, but she caught my eye as her dog not too dissimilar to my dog. And as a dog lover I felt a burning desire to stop and pat her dog and ask about him. I didn’t want to disturbing her reading though (everyone else was walking by) so I walked past too at first. I decided if she was still there after my shopping trip I’d stop and say hello.

She was. I stopped and we talked. I could tell was clearly a smart woman. She was on the ball and because she was living on the streets she had the dog in part for protection. She seemed noticeably more comfortable when I sat down on the blanket too rather than crouching. I guess not many people do that.

Then the next day I saw her again as she was sitting near my hotel. I got her some groceries, we chatted and I started to get really curious her situation.

That evening I googled what the situation was for the homeless in NYC. I wanted to see what help was available and how you should best help a homeless person if you wanted to. I learned that in the city every person has the right to shelter which means they cannot be refused a place in a shelter over night.

So then how come so many people were on the streets?

I asked the next day and she told me that no animals are allowed in the shelters, but that also the shelters can be extremely dangerous and there are often violent incidents. She had heard of three people being killed this year.

Another perspective on NYC

In between work and client calls and meeting new business friends I would stop by and see her. I noticed how when we would sit together and chat lots of interesting people would stop to talk too.

One day a published author stopped to ask if she had finished with one of his books. Another day a lady that owned an antique store. People constantly gave food as well, which was really heart warming. She told me it was fascinating to observe who would stop and talk and who wouldn’t.

I discovered that my new friend was saving to be able to get her own apartment and that so far she had $200. She had a case worker and was in touch with the authorities regularly. She told me about her family, and once we knew each other a little better, how she became homeless.

So my trip to New York was literally a mixture of lunching with millionaires and hanging out with the homeless.

Talk about worlds apart.

And the more I got to know her the more I wanted to help.

But I wondered how I could help

I spent a lot of time trying to figure out how to do this. Everyone says don’t give homeless people money – they may spend it on alcohol or drugs and I mean, what if she got mugged? It’s not as though she actually had a bank account and bank cards.

At first I had the grand idea that I would start a kickstarter campaign to get her apartment deposit.

I found out she could ‘save’ money at the mission that was helping her and it was kept in safe in an envelope under her name. I researched and found lots of different websites for fundraising and crowd sourcing. I had it all mapped out in my head.

But then I started to feel weird.

If I did that I’d have to take pictures and share my friend’s story. She had already had a bad experience of being lied to by journalists and then being plastered all over the news which really upset her and her family.

If I did a kickstarter once her picture was up it could end up being picked up by any news outlet conceivably, even though this was unlikely.

She said she would be okay with it but I could see that was only because it was a means to an end.

After digging deep I realised ultimately this was something I want to do, without judgement, or asking others to help.

A kick starter would make it a public event and I’d have to ask other people to contribute. I felt better giving directly because also it’s more personal. Then, if it was a total disaster the only money that goes missing would be from me.

So this is what happened

The amount of money she needed, while it wasn’t a crazy amount, wasn’t pocket change either. My business earns well but I also have a team to pay and I have to manage cashflow.

So I made this decision – if I get a sale overnight (by this time there was only a few days left) I’ll give her the lot. If I didn’t I’ll give her a sizeable chunk.

The universe (or God, or higher power, whatever you prefer) delivered and I got a sale which covered everything. WOO HOO!!!

So I arranged a meeting with the person she felt could be most trusted to hold the money (a minister). Until we were almost there together she didn’t ask how much I was helping with. She was floored when I told her.

So I handed over a giant wad of cash – American money is thick and the bank gave me all twenties – and got myself a hand written receipt, a huge rush of good feelings and the hope that this woman would not spend another winter on the streets.

Connection tops everything

On the way back we stopped and talked and I hugged her and we both had a bit of a cry. The human connection is so strong. Even though I know anything could happen – the minister could steal the money, maybe she’ll get a place and then lose it, maybe she will suddenly start drinking (she doesn’t now) or maybe for whatever reason beyond anyone’s control it just won’t work out.

I feel though, that just the moment where we stood there and looked into each other eyes, and somehow for both of us faith in humanity was restored, was worth it to me.

The fact that she knows someone would do that. The fact that I know if it ever happened to me there would be hope for me too.

That the world isn’t all just about getting a new dress for your VIP party. That real situations and people matter.

So why did I do this rather than donate directly to charity?

Everyone has their own way of doing good. I generally don’t give to charity because the disconnection is too great for me. I prefer to do something for one person who, for whatever reason, comes across my path in life.

When I was twenty two I lived with a Brazilian family and worked on a project in a remote town in Brazil. My first host family didn’t work out and another family offered to take me. At first the charity I was working for wouldn’t allow it because they said their house was below the acceptable standard for a westerner as they were quite a poor family. Eventually though, with some persuasion, they let me.

Ten years later the daughter from that family had the opportunity to go overseas but they could only afford the plane fare and nothing else. So I had her live with me in Germany in my one bedroom apartment and we shared a room and our lives for three months. I sent her to English school, to German school and took her everywhere with me so she could learn as much English and German as possible and so she could make the most of the opportunity.

Everyone is different. That’s my way of giving back. My Brazilian host sister has since gone on to get work in a big international hotel. That never would have been possible without the language skills she got through me and she also  got to travel all over Europe which was her dream at the time.

I hope my New York friend will be in an apartment soon (she is currently doing interviews) and can then she can start her own cleaning business, which is what she wants.

So that’s my rather personal story.

Business can be a vehicle for such good in the world right?


If this story inspires you I am still doing a few more free Business Strategy Sessions where you can get access to my advice and expertise on whatever is holding you back from either starting, or making money in your own online business. The link to book in one of these sessions is here.











  1. […] 6. Cat LeBlanc: A story of personal connection (& another reason why having a business is awesome) […]

  2. Amanda on September 9, 2016 at 8:43 pm

    This was such a beautiful and uplifting start to my day! Thank you so much for sharing this. I know it’s very personal and so many people have so many strong opinions about this kind of situation. For me this was incredibly inspiring and just the kind of way I would like to be able to connect with and make a difference to individuals.
    Like Peta said – keep us informed, would love to know what happens. Either way though you have done what you could and the rest is out of your control now.
    Love Amanda xoxo

  3. Brogan Micallef on September 9, 2016 at 5:32 pm

    Far out Cat. This story makes me cry!!

    This is one of the most beautiful things I’ve ever read. Thank you for being so honest and open, and for sharing this story.

    I hope all goes well for your friend – her future is MUCH brighter now!


  4. Peta on September 9, 2016 at 4:54 pm

    This is beautiful, gave me a tear in my eyes… I would love to know how the story continues, please keep us posted… Xo

    • Cat LeBlanc on September 9, 2016 at 5:00 pm

      I will! Thanks so much for commenting. xo

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