5 Things My Tinder Dates Taught Me About Business


I know right? Who would have thought. I’m not talking about the business of pimping yourself out (although I’ve heard that spam accounts on Tinder are everywhere). I mean your actual entrepreneurial venture.

I don’t even know if I could call 5 pictures of myself and no description on my Tinder account a dating profile.

But, as of February last year, there it was. I was ready to try it out.Translation: I was bored, curious and a little bit lonely.I’ve since moved from NYC {I’ll save that for another post} and turned the app off. But I learned a lot along the way about myself and dating, and why it’s really not that different than business.



Every. Single. Date. I went on, I knew in my gut by the time I got home (and often within the first 10 minutes) if I cared or wanted to see them again. I’m all for giving yourself time to open up and get to know someone. But if there’s something pulling at you that it just isn’t right, it usually isn’t. For me, that basically meant not seeing most people again after the 1st date. The more I started to listen to that right away, the less in my head I became. I wasn’t upset if I never heard from them again or wondering if I did something wrong.It was mutual, and trust me, the gut feeling only gets louder the longer you ignore it.

Biz translation: If something feels “off” about the client or the project, trust it. It’s a lot harder to do when there is income involved, but the long run payoff is your sanity.


I’ll call this: “OMG – he’s talking to ME?” syndrome. You know, the super hot one you show your roommate before they even say more than “Hi”.Then they say something stupid, but you keep engaging because maybe they’ll make up for it?

I tried it out a bunch of times. They never did.

Biz translation: Sometimes the big client with all the money, or the job you’ve been fangirling over for the last 6 months, really isn’t that awesome. It’s cliche I know, but when someone shows you who they are, trust it. Do your research, vet them as much as you can, and check in with yourself if you’re wanting this because it looks good, or if it really feels like a fit.


As a small caveat to the first two, maybe you’re just tired of being alone. Maybe you’re lonely and want someone to take you out so you have an excuse to dress up. Maybe you just want to hook up.

This happened with me in one case. We talked upfront on our second date about how we couldn’t actually be together for various reasons (aka Rachael stop dating international guys).

I was okay with that and we kept seeing each other for a few months. It was super fun and even a good distraction at times. There were no hurt feelings or awkward conversations. We shared how nice it was to connect with someone and feel comfortable, and that was that.

Biz translation: You might just need a client for the money. You might hate the company that hired you but it looks really good on your resume. You don’t want this to happen a lot, but sometimes it DOES. That’s okay. What’s important is that you’re honest with yourself about why you’re doing it, and if at all possible, upfront with the client or other people involved. Sometimes, they just want to use you too.


I stopped drinking at the beginning of January. As I was phasing into it, I remember telling a guy who asked me out for drinks that I was up for hanging out at the bar but just warning him I would probably only have one drink if any at all. His response: “HAHA you mean one bottle right?”


A little while later, I went out with a guy who didn’t give me a hard time about it, and I drank my soda and lime while he enjoyed his own drinks. It was probably the best date I’ve had in a long time.

Biz translation: If a potential business partner or client is asking you if you do X service (like VA services when you’re more of a Manager, or one-off projects when you want long term) you have a right to say no and let them in on what you CAN offer for them. Do this from the gate so you don’t start resenting them later when they start asking for something outside your scope of services. You didn’t let them know, so they’re going to try.


The guy I went on my very first date with turned out to have a bunch of mutual friends and went to the same University as me. We got along super well and had really honest conversations about what we were looking for. We weren’t a long term relationship match, but 10 months later I hired him to take care of my biz finances and consider him an awesome friend.

Biz translation: This kind of goes with #4, but specifically when you’re “ending” something with someone, client, partner or even a job, stay KIND and honest. Even if you might be hurt at first. This way you can walk away with no resentment. You never know what can come of it. They could come back later and it’ll be the right time, or they could refer you to an even better prospect.

In summary, it’s all about experimenting, like everything in life is.

But when you keep an open mind and are in alignment with who you are and what you will or won’t do with someone, stress and weight is lifted off of your shoulders.

And you can meet some really awesome people along the way. In business and in life.

Have you had any online dating experiences that were teachable or interesting? What tools do you use to help keep you honest in relationships, business and personal? Let me know in the comments! I would love to hear.


PhotoCreds to PicJumbo

A Letter To My Younger Self (Okay, That's Not That Long Ago)

Last week I started looking through the notes on my iPhone. and I came across something written on September 19, 2011, just 4 months after I graduated from undergrad.

I wrote a description of the ideal scene for my life in 5 years.


In five years I will be 27. By that time I hope to be successfully running by own business. I will be busy but it will feel fun and I will have plenty of time for family and friends. I will correspond with clients, readers, and friends online and make money that way. My business will have international reach and appeal. I will have paid off my student loans and be ready to buy a house. I will drive a nice car, have a personal style that shows my personality, and maybe even be engaged. I will write about my experiences and sell books geared towards girls/young women. I will have a thorough website to interact with people on. I will be involved with the United Nations in some way. I will love myself, my life, and a great man – with plenty more adventures to come. Ease, variety, love, and entrepreneurship are all things I wish for life at 27 to encompass

In four days, two years away from 27, I celebrate my first official day as a business owner.

I even have an accountant, web developer, a fucking brilliant coach, and can work from anywhere I want.

I have a tea date with an entrepreneur that I fan-girled over while reading her blog in 2012.


My Ideal Scene makes me laugh because I just remember having so much doubt.

I never could have planned for things to work out the way they have now.

I had so many nights of anxiety wondering how I would ever figure it out on my own with no savings and no real game plan.

Truth is I still have all of that fear. But reading this reminded me that I always get what I want, just not in the way I plan it.

And as for the love thing? I feel closer to being the person I want to be and show up as in a relationship than ever.

Not only that, but what I wanted in a relationship at 21 has totally changed.

Now, commitment isn’t about promising yourself to one person for the rest of your life.

It’s about committing to choosing someone over and over every day.

It’s having the tough conversations no matter how scared you are they might reject you.

It isn’t about someone else completing you.

It’s taking responsibility for your own life and inspiring each other because you do that so well.

If one day we aren’t sure we want to choose each other anymore, it’s about committing to having that conversation and giving the other person the opportunity to shift the situation. Or not.

I now believe it is possible to marry the love of your life and one day love someone else instead. But committing to the risk is better than not trying at all.


The one that was jealous of “all the other women” working from the beach, rocking amazing outfits, driving white BMW’s with their hot, successful husband next to them and inspiring people with their books?

Babe, you’re right on track.

The fear is going to feel more intense the bigger you become, but you’ll learn how to deal with it.

Those people who tell you that you’re crazy to move to NYC or leave your job with benefits? They need you to lead by example.

That belief that you’ll somehow go back on food stamp? Not true. You have amazing friends and family already willing to invest in you. And what would be so bad even if you did for a little while?

It’s not going to be easy. It’s going to feel scary and lonely and you’re going to get depressed sometimes.

But nobody who has made a difference did it because they were average.

And men? They’re not assholes, they’re human.

Hey you there, reading this. I want to challenge you to write your Ideal Scene for 5 years from now. Don’t edit or filter yourself. Lay it all out there. Include things but also how you want to FEEL. And then tuck it away. You might just surprise yourself when you read it again.

Share in the comments some of your Ideal Scene if you feel inspired. Or just let me know what this brought up for you.  

3 Vulnerable Conversations That Changed Everything


Of saying that thing that feels like its going to make you throw up on the way out or that is stuck right in the center of your chest.

Sometimes for years.

I am no master at vulnerability, but there are 3 specific conversations I had in a matter of two months that changed the way I live (and love) moving forward:


For months I felt guilty that our relationship wasn’t working for me anymore.

We barely talked, and when we did I just didn’t feel connected. I found myself not really wanting to hang out, but also not really wanting to make an effort.

Other friends told me, “That’s just what happens, you’ve been friends for like 15 years, you just change and grew apart, its okay, just let it be.”

But I couldn’t get it out of my head.

Finally, I wrote an email.

I explained how I felt in as much detail as possible, because the point (I’ve learned) is to make sure you don’t leave things unsaid.

As soon as I hit send, the grip on me released and I felt relieved.


We weren’t getting vulnerable for fear of upsetting each other, but now the pressure was released for both of us.

We have room to just let it be what it is, instead of harboring a feeling of resentment because we don’t feel heard.

I wish that friends had these vulnerable conversations more often.

Without that conversation, I would still be walking around with guilt, and feel like a part of my life was incomplete. I would also have no space for more complete friendships to enter my life.


Internally I felt overwhelmed and uncomfortable, which sometimes turned into resentment (and I felt even more shitty for having that feeling knowing how blessed I was to have the kind of position and freedoms I do).


Once I gathered myself, the first level of my vulnerable “reveal” came out in an email to my boss about what I felt like was holding me back.

I only felt partially relieved.

A week later when we caught up in person she looked at me and said, “I still feel like somethings not right – we need to figure this out for you.”

Three hours later, we had a new plan for my role and both felt excited again.

Turns out (surprise!) my boss was feeling the same way but couldn’t quite figure out what was going on either.

Getting vulnerable gave us both space to figure it out.

Without that conversation, I I would not be here taking on new clients or be able to work completely remote and from anywhere I want, which just two years ago was a dream. 


This person played a very important role in my life for multiple reasons but our relationship was always sort of “awkward”.

We let each other in (in a way that most people don’t) but we also triggered the shit out of each other.

A few years ago, when we were at our closest, I think I almost always had some version of resting bitch face on, even though inside I wanted to feel connection more than anything.

And then at the beginning of last year, it was as if my heart broke open.

I was going through a breakup and I felt like I became more loving in the process of loving myself.


It took me months because I was waiting for the “right” moment, but I told him in the middle of an argument about our relationship.

It went something like:

“Listen, I realized that I loved you back then and I just didn’t fucking understand it. I was dealing with my own stuff and you deserve to know this now because I couldn’t say it before. You are like family and I hope that will never change”

As soon as I hit send, I was relieved. The relationship no longer felt heavy or obligatory to me.

Now it feels safe.  I am excited to interact where as before I was always a bit guarded and skeptical.

Without that conversation, I would be denying myself one of my most powerful outlets of support.

I have one more big conversation left, but it won’t be the last in this lifetime.

I learned that when you get vulnerable you know the real FEELING of relief, fun, and the powerful connections. Having conversations like this becomes a little bit of an addiction.


What about you? Are there any conversations you’ve been holding in? Or have you experienced the feeling of relief through having your own conversations? Let us know in the comments below, I’d love to hear!

The Best NYC Uber Ride I Never Took

Every so often we have an experience that reminds us we are alive, that we are grateful, and that as human beings, there really is more than “the hustle” we’ve conditioned ourselves to think is the only measure of our success.

I had an experience like this recently.

Just before I went down the stairs into the subway, I saw a woman with four little kids, probably ranging from 3-11 years old. They each had a backpack and a rolling suitcase with a pillow and the woman (who I’m assuming was their mom) had a huge suitcase with her, trying to get situated so they could walk down the stairs. She looked super stressed out.

Typically I would have probably just kept moving, but I think it was the adorable Dora the Explorer backpack that made my intuition vocalize, “Do you guys need some help?”.

Immediately the woman’s shoulders relaxed and her eyes got watery, “Would you?” she said. “If you could just help him down the stairs?”

I extended my hand to the adorable little boy who immediately burst into tears and ran away from me. I tried for the next oldest kid and said, “Hey can I help you carry your Cars suitcase? I really liked that movie!” and this time he accepted my hand.

When we got to the bottom of the stairs the mother said, “Oh no, this isn’t right, I need to go to Brooklyn”. “No problem” I said, “that’s just across the street – I’ll show you” and the crew headed back up the stairs.

After a few more minutes she realized that it wasn’t the right train line at all and that the correct one was more than a 5 minute walk away. “Do you think a cab to Brooklyn would be more than $50?” she asked me. I assured her she should be okay and , I went into the street to hail them a cab.

The first man who stopped refused to take them, saying that they were too many and had too much stuff. Frustrated that I had left my wallet at home and didn’t want to just leave them stranded, I realizedI could use my Uber app and they would take them no problem.

I “called” and the (very friendly) driver came within 5 minutes and helped the family load into the car.

After they all got in and the oldest son had thanked me over and over, I gave the woman a hug and said, “This ride is on me, you guys just get there safe.” Almost immediately both of our eyes filled with tears and she insisted it wasn’t necessary. She sent me off with a thank you and a blessing.

As I waved goodbye and watched them drive away, my body was filled with this feeling I can’t quite explain in any way other than joy. And thank god I’ve learned to embrace the fact that I cry the instant my body feels joy (whether it’s a movie, watching someone sing or perform, and yes, even in a Zumba class once) I happily teared up on the subway alone at 10pm on a Thursday.

I didn’t care that I would never see the family again, that I didn’t even know their names, or that my mint.com account would now read “over budget” because of this uncalculated “expense” (which actually ended up only being $31.00).

I don’t know their story or where they were going – all I saw was a woman who had so much love for these adorable children who each had new backpacks and wheely-suitcases while hers was old and torn.

A woman taking care of them on their own and her oldest son who saw how much she was struggling and was staying strong for her.

That night, something in my gut pulled me to stop and say something. A two second feeling that our minds so often overlook and we just keep walking when we know we could help, or rationalize that someone else will stop to help them.

There have been so many times that I’ve felt a pull to stop and say something to someone, to do something that feels a bit weird or scary and ignored it. (Even as I was writing this in my local cafe, my gut told me to ask the guy next to me if he wanted to borrow my computer charger and I ignored it, so he left and walked home to get his and came all the way back. Sigh – still learning!)

But the times I LISTENED: when my gut told me to apply for a coaching program that led me to a life-changing job; when I went on a date with a really nice guy who I couldn’t explain what was wrong with him other than “something just doesn’t feel right; when it told me to email a woman I’ve never met and ask her if she’d be up for mentoring me, and she said yes.

It is never wrong – and listening serves EVERYONE involved. 

When you listen to that unexplainable pull, it starts to become more explainable.

When you listen to it, it is always LOVE.

And at the same time that there are millions of people being killed all over the world, thousands of injustices every day that freak us out and make us wonder why we are so “lucky”, there are still millions of us here who can make one small decision to listen to that love and make a difference.



P.S. That night I was so excited about the experience that I actually wrote an Uber review for once. The wrote back a week or so later with this note. Thank you Uber! 


**Hey, just FYI – Uber didn’t pay me to write or share this, and I know there is a lot of controversy around Uber in certain cities and what not. But they’re pretty great when they need to be too**

Photo Credit