Serendipity & The Art of Being Alone

View of NYC from my Hotel

This just in: the woe is me cloud from two weeks ago lifted this past weekend and I’ve never felt more myself. Wuhoo!

On a recent trip to New York City for work, I followed all of your advice and I slowed down. Way down. So much that I didn’t even tell anyone I was going to be there. Sorry to any New Yorkers I didn’t get a chance to see!

I selfishly left the weekend wide open for myself to just be me – to traipse around and do whatever I felt like at any given moment. No plans, no commitments.

Actually, I did have a plan for the weekend, but it didn’t work out. When Plan A failed I was determined not to let it ruin my weekend. So I quickly moved to Plan B: enjoy Manhattan and be FABULOUS. Get dressed up just for fun. Spend time alone without cramming my weekend full of plans and see what happens. And let me tell you, the Universe delivered.

Dancing, Dining and Shopping Solo

I’ll spare you the diary-like entry of exactly what transpired over the weekend and just give you the highlights of my time alone:

  • On Friday night after Plan A didn’t work out, I had dinner by myself at The Standard Grill. The Food & Beverage manager sent over dessert and champagne on the house. We became friends and he took care of me for the rest of the weekend.
  • On Saturday morning I went to yoga class outside overlooking the Hudson River with a view of the Statue of Liberty. Heavenly.
  • After yoga I put on my favorite dress, walked down to the Christian Louboutin boutique, and checked a big splurge purchase off of my life checklist.
  • I met an amazing woman at the Louboutin store and we became instant friends. We went to a two-hour lunch at The Collective, then she snuck us into the Bagatelle Bistro (a famous brunch spot with a daytime DJ), where we spent the rest of the afternoon dancing on booths and sipping champagne. (Here’s a great article that describes the experience)
  • When I got back, I started breaking in my new shoes by dancing around my hotel room before Saturday night’s solo dinner. Fabulously fun.

So those are the highlights! Sure, there were lows. But for each one, I quickly picked myself up. I made the effort to look my best (even if I didn’t always feel my best at first) and go out alone. In return I made new friends, had great new experiences, and most of all – rediscovered my sense of freedom and confidence. I felt proud of myself again.

I was reminded this weekend that when you honor yourself and make (what can be hard) choices to slow down and spend time alone, the Universe takes care of you. Thank you Universe for taking care of me.


P.S. New York City, I love you. I hope I see you again soon.

P.P.S. On a completely unrelated note, my friend Kevin Smokler is looking for two unpaid interns to work at this summer. As Kevin says, “The internship is technically unpaid but we fully intend to shower said interns with free books, gift baskets, good will and career advice/introductions.” Sounds awesome! If you’re interested read more here.

{ 42 comments… read them below or add one }

Kate June 8, 2010 at 6:17 pm

I'm so glad you got to enjoy NYC! I think your next trip needs to be to Philly, so we can hang out and meet awesome people. 😉


Emily Smith June 8, 2010 at 7:22 pm

Wonderful article, Jenny! It is always wonderful to hear reassurance that it is alright to spend time with/honor yourself.

This post reminds me of a dove chocolate I ate the other day and inside said ” Be your own best friend.”…..


Debbie June 8, 2010 at 8:00 pm

I love you Life Checklist Jenny, and I love that you now own two new pairs of Louboutins. Learning how to walk in them is on my checklist! Thanks for sharing your rejuventating weekend


doniree June 8, 2010 at 10:48 pm

I LOVE this. Love it. Some of my best memories are of traveling alone – well, not the whole trip, but taking solo moments for myself. Even just learning how to navigate a place solo can give you such a feeling of accomplishment, and dining alone? I adore it. Perhaps sometime I could travel alone with you :)


jennyblake June 8, 2010 at 11:32 pm

Thanks so much Kate! And yes – I definitely need to make a trip to Philly in the near future. I'll let you in on a little (okay HUGE secret) – I got a book deal, and my publisher (Running Press) is based there. So I definitely plan on visiting some time in the next year! Going to post about that on my blog any day now… :)

Have a great week!


jennyblake June 8, 2010 at 11:33 pm

Thanks so much Emily! It's amazing how liberating it can feel to make the CHOICE to be alone (or slow down) rather than feeling forced to or like you don't have a choice. And I love that dove quote! I really did feel like my own best friend this past weekend, and it was so fun :) It reminds me why I like traveling so much. Have a great week!


jennyblake June 8, 2010 at 11:35 pm

Thanks Debbie! I created a template version of that you can use if you want to:….

As for learning to walk in the Louboutin's – totally! That's why I've been wearing them around my house. Well, that, and I'm determined to get my money's worth 😉 Do you have a pair? I feel like a million bucks just knowing they are in my house!


jennyblake June 8, 2010 at 11:36 pm

Thanks Doni! Funny, I was just about to go comment on your post – I loved yours too!! I totally had a “being in the moment” weekend and it was so much fun. Even though there were some big ups and downs, I felt so present, and that was such a gift. I love dining alone too! We'd make great travel companions…lots of comfortable silences I'd imagine :)


niferann June 9, 2010 at 12:46 am

Good for you, Jenny! Your weekend sounds amazing. I'll admit, I still get intimidated about going out alone most of the time, but your experience just proves that good things happen when you have a good attitude.

I've had a craving to visit NYC, and you just might have inspired me to take a solo trip if no one will go with me!


Ali June 9, 2010 at 12:47 am

Yyyyyep, this sounds absolutely amazing. I miss my home state SO much, it hurts sometimes!


HappinessandWisdom June 9, 2010 at 12:49 am

Slow Down! is such great advice. I've found it works for me (when I choose to do it), but I am inspired by your post……perhaps I'm not slowing down enough! What struck me was your ability to connect with people. Perhaps that's just your way, but I suspect it had to have been due, in part, to slowing down and noticing those around you. Very interesting – thank you!


Jenny Ferry June 9, 2010 at 1:03 am

OMG! Thanks for sharing about your *amazing* solo weekend in NYC and reminding me that nourishing yourself through self-friendship and sporting high-heels are some of the most valuable, heavenly times on earth. :)


Eve June 9, 2010 at 2:34 am

Whoa! So awesome. But where's the pic of your new Christian Louboutins? 😉


andi norris June 9, 2010 at 4:08 am

Oh I am so glad you took care of yourself! Those ruts are nasty to weasel your way out of, especially with plans not working out. It sounds like your weekend was unbelievably fabulous though!


Ann Elizabeth Grace June 9, 2010 at 7:47 am

Awesome Jenny! There's something so freeing about traveling solo…even for a simple jaunt to a new part of town. Wonderful to hear that a trip across the country brought you back home to yourself. Thanks for sharing!


Positively Present June 9, 2010 at 11:45 am

Making time for yourself is SO important and I'm so glad you did this. Very inspiring post!


Marian Schembari June 9, 2010 at 1:31 pm

Dude, that dress? Yeah, it equals RIDICULOUS. I want it.


TMFproject June 9, 2010 at 3:37 pm

YES yes and YES.

Precisely why I prefer to travel alone. I've had the most amazing experiences with the most amazing people that I met serendipitously–and probably wouldn't have if I were in a group.

Ashley <3s Jenny.

The end.


jennyblake June 10, 2010 at 12:59 am

Thanks Ali! New York IS amazing – awesome that that's where your from…I hope to live there for some day (even if it's just for a month to start). Have a great week!


jennyblake June 10, 2010 at 1:01 am

Happiness and Wisdom – thanks so much for stopping by! I think you're onto something – me meeting so many people had a lot to do with just putting down my phone and actually making an effort to sit, be quiet, smile and converse with those around me. I'm just hoping I can replicate it now that I'm back in my everyday environment :)


jennyblake June 10, 2010 at 1:01 am

Thanks Jenny!! Loved your recent post too – you are FABULOUS inspiration for me! And I've been wearing my high heels just to answer emails in my house. They automatically make me feel like a million bucks! xoxo :)


Gloria June 10, 2010 at 1:03 am


I have to admit I wish that I could plan more weekends to just myself. Although your plan A fell through, don't you think its important to find some mental clarity by spending time with oneself? For me that usually means literally being alone as in not around other people. I love the peace and quiet. Considering you had such a good time alone and even made a new friend along the way, I'm going to make an effort to spend a day out in the city (Chicago not NY) and attempt my first solo dinner!


jennyblake June 10, 2010 at 1:03 am

Thanks Eve! And great talking to you the other day (Neil says the book is in the mail…sent three weeks ago so hopefully it will get there soon?).

Here's a link to one of the pairs I bought (other pair is the same style but in peacock blue :)


jennyblake June 10, 2010 at 1:04 am

Thanks so much Andi! You have been so supportive…and we've never even met. I CANNOT WAIT FOR THAT DAY TO COME!!! Hope you're having an amazing week 😀


jennyblake June 10, 2010 at 1:04 am

Thanks Dani! It really felt like such a “present” weekend – those are such gifts!


jennyblake June 10, 2010 at 1:05 am

Thanks Ann! It's always great to hear from you – I hope all of your travels are going well…we should catch up soon!


jennyblake June 10, 2010 at 1:07 am

Thanks girl!! Anthropologie – great for super girly “I am fabulous hear me roar” dresses. Here's the link if you seriously do want it!

Thanks for stopping by – your comments always crack me up!!!


jennyblake June 10, 2010 at 1:16 am

Wait, you have the equation all wrong…

JENNY <3s ASHLEY x 3,000%!!!!!!!

You are a shining model of fabulous glory when it comes to traveling alone and blazing your own trail. I love every second of it, and I CANNOT FREAKING WAIT to meet you in person and just exude so much fierceness that SF doesn't know what to do with us. BOOM! Here we come.

But in all seriousness, it's so true – traveling alone, putting DOWN electronic devices, and not making all kinds of plans are the best way to meet people. Seems so simple, but not always an every day thing (for most of us).



jennyblake June 10, 2010 at 1:19 am

Gloria – thanks so much for your comment. Since I tend to stuff my feelings down – I agree with you that sometimes I think it's important to get mental clarity and not immediately fill the empty space with people and distractions. In this case, after disappointment from a boy, I needed to go out and show the world that I was still fabulous! It just felt like the right thing to do at the time, and I'm glad I did 😀

Your day in the city and first solo dinner sounds FANTASTIC!!! Will you keep me posted? I'd love to hear how it goes! I say get dressed up, square your shoulders, and be proud that you're putting yourself out there like that 😀

Have fun!


Eve Ellenbogen June 10, 2010 at 4:07 am

Dear god, those are some high (and fabulous) shoes. I'll just have to start calling you Carrie. And thanks for finding out about the book! It'll be like Christmas (okay, Hanukkah) to find it in my mailbox.

Did you say TWO pairs? How can I get me a job at ol' Google???? 😉


doniree June 10, 2010 at 1:23 pm

Perhaps we should try that whole “travel together” thing some day :)


Arrangedinlove June 10, 2010 at 1:24 pm

Sounds like a great time in NYC!! How do I sign up for the yoga class overlooking the Hudson River?!


Elisa Doucette June 10, 2010 at 2:32 pm

It's interesting how the Universe delivers to us in situations like these. But only if we are open to hearing what it has to say. A year ago I don't know that I would have been able to even think about getting all gussied up and taking my fabulous self out on the town. To which the Universe would have been impatiently rapping it's fingers on a desk saying “Stop moping…do you KNOW what I have in store for you?!”

Kudos to you girly girl and thanks for the great reminder of what can happen when we realize how wonderful we all are, even if we are “just” alone. :)


jennyblake June 10, 2010 at 5:12 pm

HAH! They are very high…make me about 6'1!! Which is why my man requirement has a height minimum of 6'2 :) I know, too picky.

And I couldn't help but get two! I'm SOOO indecisive! It's expensive, I know. You don't need a job at Google – you can just move into my house with my friend Elisa and I'll support the both of you 😉


jennyblake June 10, 2010 at 5:14 pm

Thanks! And the classes are offered by The Standard Hotel (Meatpacking district) – check out the schedule here:….

You should totally try one!


jennyblake June 10, 2010 at 5:17 pm

Elisa – YES – you are so right – we have to be open to listening. When I'm in my total cloud/funk, I'm really not hearing much of anything – just feeling sorry for myself. But there is something beautiful about being sad AND open at the same time – people really came answering.

Oh and one more thing – THANK YOU. Thank you for lifting me back up and helping me square my shoulders and carry on. I could not have done it without you.



benjamintwilcox June 13, 2010 at 12:12 am

Being alone is something that I have been working on lately since moving to a new area of the country. I love the way you feel when exploring an area by yourself. My last trip to NYC was much like you described when I was navigating the subway on my own.

I love this idea, and as much as others have said this in the comments below, the chance meetings of friends/barristas/fellow travelers is exhilarating. I know that traveling with a few friends can also yield the same results. In Vegas, my buddy and I ran into a man who claimed to be Evil Knievel's manager with the 70s wallet photos to prove it!

Great to hear that you are out of your rut and taking the world by storm!

PS: Congrats on the book deal! :)


Chinarut Ruangchotvit June 15, 2010 at 8:02 am

woo hoo! i'm so glad to hear you found yourself DANCING by day – so touches my heart! daytime DJs are the BEST! you're gettin us all revved up for the summer! :)


jennyblake June 16, 2010 at 10:04 pm

Thanks so much Ben! You've definitely taken a huge leap this year – and so true what you said about having those crazy experiences alone or with friends. Funny, some of my best “chance” meetings happen in Vegas too! Vegas is just guaranteed to throw crazy new people/experiences your way :)

Thanks so much for the book congrats – I hope you're having a great week!


jennyblake June 16, 2010 at 10:07 pm

Thanks so much Chinarut! Dancing during the day (with DJs) is the BEST!!! I hope all is well with you – and that you have lots of summer daytime dancing planned in your future! :)


Laurie Zerumsky April 7, 2011 at 3:39 pm

heard that kate! I second it! Come to Philly! You need a big hug from me! You are insanely inspiring!


Javier April 9, 2011 at 6:07 am

Te gustaria pertenecer a un club que no admitan a socios como tu?
Would you like to join a club that doesn`t accept people like you as members?
Studio jjcuper bilbao


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