You Have To Start Somewhere, So How About Right Now

8 Aug

(And other wisdom gained during a summer of transition)

StartingBloc NY ’12 commitments. Photo credit: Jeff Wenzinger

At the end of May, I quit my job with the intention of not living one more day failing to live up to my full potential in life.

It sounds so simple when you spell it out, as my friend Evan did for me one evening back in February on a Santa Monica rooftop overlooking the Pacific Ocean:  why would you do anything in life other than maximize your unique impact on the world?  Why would you ever stay in a job you don’t like and live in a city you don’t like?  Yet so many of us, including myself for several years, get stuck; we get stuck in jobs that don’t make us happy, we get used to mediocrity, and grow so accustomed to the routine of exercise/work/happy hour/party/Facebook/sleep (repeat), that we stop caring or trying, and we completely bury our passions, our creativity, our art, our unique voice.  Sometimes television and the news and alcohol and social media or even relationships help us forget, because they take the focus off our own selves, and allow us to forget who we are and what we are truly capable of achieving. 

 When you leave your job without 100% knowing what’s next, it’s really hard and really scary, and sometimes people laugh at you and sometimes you laugh at yourself.  “You left a job paying WHAT and job security for the next gazillion years to be a freelance writer?!  You’re nuts!  Wake up man!  It’s 2012!  Have you heard of a little thing called the recession?!  Writers can’t make money, journalism is dead. You’re moving to San Francisco— rent there is 450 times what it was two days ago— haven’t you seen the infographic?!  You’re competing for jobs with 2,000,000 other 29 year-olds with bachelors degrees from New England liberal arts colleges and no hard skills, you’re so screwed.  THE BUMS WILL ALWAYS LOSE MR. LEBOWSKI, THE BUMS WILL ALWAYS LOSE!”

The goals I set for myself when I left my job were to pursue my interest in writing, support social entrepreneurs, make others happy, and to empower people to live out their full potential in life.  To this end, I am succeeding so far, as this summer has given me time to travel, to explore, to learn, to grow, to write, to meet emerging social changemakers, to be inspired, to network, to find a tribe of people who believe in what I’m doing, and build the confidence necessary to move forward.

Tomorrow I finally fly out to San Francisco.  It’s been a long time coming, I’m only just getting started, the journey is only beginning, and I have so much work that lies ahead.  So I thought I’d offer some wisdom I’ve gained thus far, a few things I’ve learned this summer, for anyone else out there is going through a similar transition, or who is thinking about quitting their job or making a major change in their life. 

The beautiful thing about wisdom is that it comes from within, but it is sparked by the experiences you have with others; to that end, I am grateful for all of those who have touched my life this summer in such magical ways.  I’d like to particularly like to recognize the bold, inspiring, unreasonable, friends I’ve met this summer while spending time at StartingBloc BOS ’12, The Bold Academy, and StartingBloc NY ’12 as well as brief visits to The Unreasonable Institute and the Dell Summer Social Innovation Lab; communities of people whose passion for social change is so fierce you can’t help but become a better version of yourself.    

1.    You are already awesome.

 “Our job in this lifetime is not to shape ourselves into some ideal we imagine we ought to be, but to find out who we already are and become it.”  -Steven Pressfield

I used to think that finding out who you are or what you’re going to do next came from talking to your friends and reading self-help books and seeing self-help counselors and doing lots of yoga and going on a pilgrimage to a temple somewhere in Asia.  While all of these may help, it’s easier to just look in the mirror and holler at yourself.  Who are you?  No, seriously, who are you?  What do you care about?  Where do you want to live?  Where do you not want to live?  What do you like to do?  What do you absolutely hate doing?  What are you good at?  What makes you happy?  What makes you upset?  What do you want to change in the world?

I had the amazing opportunity to spend a week in July at The Bold Academy in Boulder, Colorado, a real-life school for superheroes (if you don’t know, now you know!), created by Amber Rae and Nathaniel Koloc, which brought together 20 young people for a month-long journey in unlocking individual purpose and collective human potential, where I learned a simple but essential truth:  All of us are awesome and all of us have a unique, essential contribution to make in this world.  YOU.  ARE.  AWESOME.  Repeat it four times.  And then tell your friend so she knows she’s awesome too.  My brilliant friend Denise calls this self-love.  It will set you free. 

2.  Don’t front on the unstoppable power of someone with an idea and a passion.

“Look in your own heart.  Unless I’m crazy, right now a small voice is piping up, telling you as it has ten thousand times, that calling that is yours and yours alone.  You know it.  No one has to tell you.”  Steven Pressfield

When people look within, find their interests and passions and unlock their human potential, it’s magical.  It’s unstoppable.  It’s contagious.  If you need any motivation, like I did, check out how StartingBloc Fellows are using social innovation and entrepreneurship to change the world, or check out the brilliant Unreasonable Institute Fellows.

Unreasonable Institute Fellow Sheikh A. Turay’s passion was so electric that his company, Liberation Chocolate, a social enterprise that employs former child soldiers in Liberia to revitalize cocoa plantations there, was re-launched in one afternoon in Boulder, Colorado.  At the Unreasonable Scrimmage, an all-day event hosted by The Unreasonable Institute and ReWork to engage Boulder community members in rapidly protyping social business models, eight people came together in the span of four hours to help Sheikh establish a U.S. distribution channel for his product, find a local chocolate producer, develop a new branding plan, and create a new website.  Why?  Because passion is power. 

3.  Gain wisdom from people younger than you are; they hustle harder

Prior to leaving my job I had a little bit of a chip on my shoulder when it came to taking advice from young people in college or just out of college— sort of “I’m in my late 20s dude, you’re in college, you don’t know shit, talk to me after you’ve had a real job or two, after you’ve paid rent and had to pay off loans for a few years”—basically, I thought I was above listening to someone younger than me.  Not anymore.  Some of my most important mentors and the people I look up to most in life are 7-10 years younger than me.  Ted; he’s 22, he founded a nonprofit that teaches financial literacy to urban teenagers, he’s taught me infinitely more about smashing fear and setting audacious goals and being hungry and tenacious than any 30-80 year-old I’ve ever met.  Sam; she’s nine years younger than me, she has about 10 business projects going right now, knows everyone in the world of social entrepreneurship, and she inspires me to hustle harder.  Burcu; she worked at The Bold Academy this summer and made magic happen, she just graduated from college, and has already made a profound impact on the lives of so many people.  

Young people are tenacious, they are bold, they stop at nothing to get what they want, and most importantly, their deepest motivations come from connecting a personal interest with a social problem bigger than themselves.  As we get older we tend to immerse ourselves in the minutia of own lives; we should all spend more time listening and learning from young people, and following their lead for how we can make the world a better place.  

 4.  You have to start somewhere, so how about right now.

“Whatever you can do, or dream you can, begin it.  Boldness has genius, magic, and power in it.  Begin it now.” –Goethe

 I used to love imagining the future.  “One day, I’m going to live in San Francisco.”  “One day, I’m going to write whenever and whatever I want to write and not just write at work.”  I kept putting off my dreams for some perfect moment, some perfect time when the stars were going to align and bagels and lox were going to start flying down from the sky.

You know what?  The stars are aligned right now.  That perfect moment is now, the future is today.  You have to start somewhere.  “But I don’t really know what I’m doing.”  Nor do I, nor does anyone.  So start right now.  Start writing, start the blog, start the new venture, buy the plane ticket, begin now.  What are you waiting for? 

I had the honor of meeting Alex, aka DJ Doce Luna, at The Bold Academy in July.  Alex is a Grammy-nominated jazz musician, and he’s launching a new career as a DJ/producer.  In the span of several weeks, he launched a new website and social media platforms, recorded an album and multiple other tracks, incorporated his business, found several business partners and is starting to book gigs.  In other words, he’s killing it.  Why?  Because he started. 

5.  Happiness and making money do not correlate  

It’s very nice to earn money.  There are millions of people in the world living in poverty who would like just some of it, while a very small number of people have way too much of it.  But, from my experience leading two “job/career change” discussion groups at StartingBloc this summer, making money and being fulfilled do not usually go hand-in-hand.  I can’t count the number of conversations I’ve had this summer with young professionals working well-paying, impressive jobs at notable corporate law firms, management consulting companies, government agencies, investment banks, nonprofits and smaller companies, who are miserable at work and in life because they are not being challenged and because their heart and their passions and theories of social change are not connected to what they do every morning at 10am.  

A paycheck is important.  It’s cool when someone sees your resume or your business card and is impressed.  But happiness comes not at happy hour when you’re bullshitting with someone and pretending to be happy while you are really miserable, but only when you are actually impressed with yourself; that is, when you are doing what you love.  I’ve gotten more personal joy in the last two months from sitting down and typing a few words that came from my heart, taking a risk by putting my words out there into the world (which I had rarely ever previously done), and then hearing from a reader that the words were inspiring and made him want to do something different with his life, then I did from countless months of direct deposits in my bank account.  Obviously, we all still need to make a living, we still need a job, but it’s not about the money; it’s about finding a job that works for you, your unique skills and passions, and the impact you want to make on the world. 

6.  You can’t do it alone, you need a tribe

Putting yourself out there is not easy.  Anyone who tells you that it’s easy to make a major life transition or quit your job or start your own business, is full of shit.  You simply cannot do it alone.   You need to find your tribe; a group of people who believe in what you are doing, who will do everything in their power to help you succeed, and will bring you back up when you fall down or start to doubt yourself.  Communities like those at StartingBloc and The Bold Academy; communities of love, communities of support, communities of affirmation, communities of “I got your back,” of “I feel you,” of “I can help,” of “you need to hustle harder” of “let’s hold each other accountable.”

When you find your tribe, victory is a constant because when one person in the tribe accomplishes something, whether it’s launching a new website or winning a fellowship or getting press recognition or raising money or writing a blog post or recording a new song, the rest of the members in the tribe also win. 

 7.  Be grateful

 We only get to where we are because of those who carry us.  Thank you to my tribe and my friends who continue to carry me through this challenging transition.  You have helped me become a better version of myself.  I love you and am forever grateful.  Time to hustle, ready, set, go. 

38 Responses to “You Have To Start Somewhere, So How About Right Now”

  1. Bob Maszczak August 8, 2012 at 1:20 pm #

    Great post, Smiley! Many folks I know spend their entire lives going through the motions of the daily grind without taking this first step. I am very grateful to hopefully be counted as a member of your tribe of support and love. Enjoy the journey. The Universe has so much in store for you!

    • whatsupsmiley August 8, 2012 at 8:58 pm #

      Thanks so much Bob, you are family– the most important tribe there is! Thanks for always supporting me and giving great feedback on my writing– hope to see you soon!

  2. Jennifer Chen August 8, 2012 at 1:28 pm #


    Thanks for the awesome post!!

  3. Sam Solie August 8, 2012 at 2:20 pm #

    AWESOME post, Smiley! Keep it up brother, and I’ll see you sometime soon in San Fran!

  4. samsonthewarior August 8, 2012 at 2:20 pm #

    AWESOME post, Smiley! Keep it up brother, and see you soon in San Fran!

  5. Millen b. Paschich August 8, 2012 at 2:21 pm #

    Good words!

  6. nevaehmarie August 8, 2012 at 3:25 pm #

    I am so moved by your post. I am sitting in my office, was searching on some of my favorite positive blogs this afternoon prior to lunch, and found this post from Amber Rae (one of my most visited blogs). I cannot thank you enough, I am inspired and have shared this with family and friends in hopes they too will be inspired by your testimony. I look forward to your journey!

    • whatsupsmiley August 8, 2012 at 9:00 pm #

      Many thanks for the positive feedback– Amber Rae is an inspiration to me as well! Thanks so much for sharing this message with others…

  7. Lolly (@lollyjean) August 8, 2012 at 3:37 pm #

    Inspiring and moving post, here! Looking forward to following your journey and to reading more of your words. I don’t live too far from SF, would love to meet up!

  8. Evan Walden August 8, 2012 at 4:43 pm #

    Smiley…I am so proud of you for this AMAZING post and for the progress you have made over the past few short months. You worked your ass off for this and I can’t wait to follow your success. I’m always here to give you a hand up, or to kick you in the ass, whichever you may need ; )

    • whatsupsmiley August 8, 2012 at 9:03 pm #

      Evan– thank YOU brother, thank YOU. It all goes back to LA. I’ll need that motivational talk soon, I’ll be in touch…

  9. Jai August 8, 2012 at 5:36 pm #

    You have no idea how much I needed to read this Smiley, oh wait…you totally do because you’ve already lived my current predicament. And that’s why you’re my inspiration.

  10. Amber Easton August 8, 2012 at 9:21 pm #

    Thank you, Thank you, Thank you. This was very inspiraional and exactly what I needed. I am so happy for you and honor your courage to nuture the person you are meant to be and pursue the life you are meant to live. Awesome!

  11. Shira Bee August 8, 2012 at 10:12 pm #

    Smiley, I’m fairly confident you already know how much I love you and how much I love to hear your heart, soul, and wisdom come through in your writing, and this is a beautiful example of just that. So so so inspiring, a wonderful reminder of how lucky I am to have been able to check in and watch you move through the process back from LA’12 to BOS to NY to SF!

    love & hugs & looking forward to seeing what comes next!

    • whatsupsmiley August 8, 2012 at 11:50 pm #

      LOVE you Shira! It’s been quite a ride since February… the journey continues!

  12. Udo, the Girl August 9, 2012 at 12:27 am #

    Cool to read someone be open and honest about their journey like this. I’m stuck on finding a community. 😦 I have to keep going, thoug.

    • whatsupsmiley August 9, 2012 at 1:06 am #

      Thanks Udo! Keep looking– it’s not easy to find a truly supportive community, you may have to look outside the normal group of friends who you hang out with (which can be difficult and awkward…), but it’s so crucial to find this community. Keep going and by doing things you care about, you’ll build it.

  13. Chelsea August 9, 2012 at 1:40 am #

    Nice work, Smiley! I’m inspired and will return to this entry for inspiration as I move forward on working towards making my own dreams happen. Thank you. 🙂

  14. anandsinghblog August 9, 2012 at 5:37 am #

    very inspiring post ! this one. it’s very true that money and satisfaction never go hand-in-hand. One has to discover oneself and make our passion into a vocation,then life would be a bliss ! 🙂

  15. JB August 10, 2012 at 4:43 pm #

    Great post Smiley. I remember this conversation we had very well and still think of it often. Just fyi, the school of visual arts photo is actually a beautiful work of graphic design done by one of my best friends in the whole world, John Passafiume. He hails from Louisville, KY, but currently lives in Brooklyn. If you liked that checkout some of his other works as well as he has won some international awards over the years. I hope all is well in the Bay Area!

    • whatsupsmiley August 11, 2012 at 9:13 pm #

      Thanks JB– John’s work is indeed beautiful– everyone in the room while we were at SVA was admiring it… Hope all’s well!

  16. epiphanyconcepts August 11, 2012 at 6:15 pm #

    Number 6 and 7 totally resonated with me, Smiley.

    A supportive and loving community that can respect that this is YOUR journey, makes all the difference. It’s easy to get caught up in our head. And get lost in the noise of who the world tells us to be. Our tribe reminds us who we are. Encouraging us to KEEP THE F@#K GOING!

    Gratitude keeps our heart open and able to receive the challenges as lessons. Appreciating them as feedback as to what doesn’t work — and what does.

    Thanks for the reminder, amigo. YOU are simply awesome.

  17. Mike August 18, 2012 at 3:08 pm #

    This is such a great site. Number 5 is right on. I make so much less at JVS than when I was kicking it in real estate but it is SOOOO much better. The work is super rewarding and you are really helping people, not just personally profiting from helping people….big difference. And number 3, good news Adam….when you get to be my age you really respect the opinion of younger people because EVERYBODY IS!

  18. Jen December 10, 2012 at 9:05 pm #

    Hi Smiley. I just found your blog, through my stepmom, who is your aunt. This post… this post nailed it perfectly. I remember exactly how it felt to walk into my office job in Chicago and put in my 2 weeks notice. They asked me what I would be doing instead, and I told them I was starting a sustainable farm with my boyfriend. I must have sounded nuts. But now, we’re doing exactly that. We’re married now, living in PA, and we grow vegetables and this year, started a CSA. It’s not easy. But the easy life of pushing papers across a desk for someone else was mind-numbing and depressing. This is an amazing adventure, and I’m grateful for it. If you’re interested, come visit out blog at

    • whatsupsmiley December 11, 2012 at 2:23 am #

      Thanks Jen! Who is your stepmom? So glad that you two followed your heart and are doing well with the CSA, proud of you!

  19. Rachel Rowland March 18, 2013 at 6:21 am #

    Oh Smiley, I love this post!!!!

  20. Kevin F. Adler (@heyKFA) April 13, 2013 at 10:41 am #


  21. Liz July 1, 2013 at 5:45 am #

    Hi Smiley, found this through a share from the Monday Night Activity folks. I so resonate with #3 – there are SO many amazing young people doing creative and powerful things and for some reason I get totally hung up on the fact that they’re 10 years younger than me and virtually refuse to listen/learn. Even though thinking back to myself in my early 20s, I was taking way more risks and getting way more amazing things done. With age may come wisdom, but also over-caution. It’s great to hear someone acknowledging this age hangup – it brought awareness to the feelings of embarrassment I get when I’m the oldest person in the room, and inspired me just take a breath next time see what there is to learn.

    • whatsupsmiley July 1, 2013 at 8:02 pm #

      Thanks so much Liz for this thoughtful comment. Exactly– you can learn from anyone, old or young. So important not to judge people before you hear what they have to say, or learn what they’re about. Thanks for reading!


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