The Moment You Knew

The Moment You Knew

I’ve spent much of the past four months interviewing unconventional entrepreneurs for my next book, and throughout the process I learned what kind of questions solicit the best answers.

For example, I often asked people whether their venture was “worth it,” which might sound simplistic. Of course it’s worth it! I’ve learned, though, that this question often leads to a good story, so that’s why I ask.

I also learned to ask if there was a specific moment when they knew for sure they would make it. These “moment they knew” stories can be fun and inspiring.

Here are three of them, from different parts of the world.


Even with our excellent credit history, 2010 was a bad time in banking to ask for money. We didn’t need much, but we couldn’t swing it completely on our own—my husband Jon and I needed a small credit line to lease the building where we planed to house our interior design and framing business. Unfortunately, the bank said no.

Later that day, Jon was on the phone with the landlord of the building telling him that we just weren’t going to be able to make it work, and that he could release the building to the other interested party. As I heard him saying those words on the phone, I had an incredible surge of hope and I remember shouting, “Jon, no! We have to give it another shot! Tell him we just need a few more days to try again. We’ll just go back in to the bank and make them hear us out. If they’ll just sit down and listen, they will believe in us.”

It totally worked! The bank did hear our plea, and we eventually got what we needed to get going. But we almost just accepted the fact that “it wasn’t meant to be” and carried on with our lives. I am so glad we put it more effort; it meant everything to us to give it one more passionate plea.

Karen Starr
Hazel Tree Interiors
Akron, Ohio


My husband and I were traveling around Europe after I had been hit by a car. We were going to travel and then go back to Chile to shoot weddings until the bookings stopped coming in and then go back to having “normal” jobs. We had been Couchsurfing to try and save money, but after a month and a half on the road I was sick of it. So we decided to splurge in Italy. We checked into an amazing room at the Meridien, and I decided to pay an ungodly amount to use the internet for ten minutes. And that was when I saw the email. It would be our second U.S. wedding and our first U.S. wedding where I had quoted more than simply travel costs. The bride had decided to hire us and she was going with our biggest package, over $5,000.

I freaked out. I called my mom and then I called my dad screaming—stupidly using the hotel phone, which ended up costing another hundred bucks. I should’ve paid for another ten minutes of the internet and used Skype. I wasn’t freaking out because of the money, though. It was more that for a bride to pay that amount of money to photographers that don’t even live in your country is a huge leap of faith. And that was when I realized—if there was one bride willing to hire us and fly us in, there were probably more. And I started to think that if we could work both in Chile and outside of Chile, we could make this work.

So we did.

Kyle Hepp
Independent Photographer
Santiago, Chile


The big day for us was August 20th, 2008—also known as the day when we realized our dream of moving back to my partner’s native Spain. When we set up the company in England in 2005, it was with the aim of eventually being able to move back to Spain and run the business remotely, although we weren’t sure of how long this would take. We had set up a perfect infrastructure, with cloud-based business management software, VoIP telephones, and so on, but the logistics outsourcing was the proving the biggest hurdle. We couldn’t find a company that could deal with the complexity of 250 different products, most of which were labelled in Spanish.

When we finally managed to set up the contracted out logistics operation, and drove away from the warehouse knowing that we no longer had to do the picking and packing ourselves and that the following day we were getting on a boat to Spain, I knew we had achieved what we set out to do.

Jonathan Pincas
The Tapas Lunch Company
Spain and United Kingdom


The stories are powerful because they provide a keystone moment when someone goes from doubt to confidence. When you have these moments, hold on to them. Remember them the next time you encounter a big challenge.

How about you—when did you have an experience where you knew your project would be successful?


Image: Chicago Man

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  • Mandy says:

    Very cool. The photographer’s story is especially inspiring to me (I’m a photographer too). It’s so awesome when the universe validates that you’re on the right path!

  • Luther says:

    I can’t wait to read the book! These excerpts are great, especially the story about being hired for photography in Chile! I know that feeling of the the first money coming in being disproportionately exciting for what it represents. If there is one, there are many! I remember when I hit the $1,000 mark for my first seminar on health and vitality, I knew this was the beginning of something exciting and that I was finally going to be able to live my passion and get paid for it. Thanks for everything you are doing.

  • David Siteman Garland says:

    Best part about your next book will be that I’ll be stealing the folks you interview and interview them on my show lol.

    But seriously, that will be happening 🙂

  • Scott McMurren says:

    Those are great stories, Chris. I had a couple of moments… but not like the ones above. Mine were somewhat defensive in nature. The first was getting fired via voicemail on New Year’s Eve. The other was getting fired by a person who was wholly unprepared for the task of managing people. These two events helped me realize that I simply had to find a better way to achieve my goals… even though I was trained to work hard and get the job done, the entire employer-employee setup didn’t work for me.

  • Tom Ewer says:

    Unfortunately, I don’t yet.

    The first story does illustrate something vital though – you can be right on the edge of giving up before getting that little bit of impetus you need to carry on and eventually experience success. A lot of people do actually give up before they get to that point – and that is what I am determined not to do.

  • Alyzande says:

    Today I made the leap and became officially self employed as a “web entrepreneur”. I just wanted to share that with someone.

  • Deborah A. says:

    I’m still waiting for ‘my moment’! lol These stories give me a little added hope that it will come. Looking forward to reading the completed book!

  • Karl - Stepping Into Wonder says:

    I love it, example of moving from doubt to confidence.

    One example for me is when I worked on publishing my graduate research. In the beginning I thought it was going to be impossible but I reached a point with my coauthors where we really believed in the quality and value of our research. One after another all three manuscripts that I submitted were published!

    We must constantly ask ourselves: “Is your fear of failure greater than your desire to succeed?” (Zig Ziglar)

  • Bruno says:

    The moment when “I just knew” was when I decided to quit my job in PR industry and to start project of interactive dinners for foreign guests in Croatia (Europe, next to Hungary, Slovenia and Italy by sea). I have named it Crosmopolit and started with making a website (, a lot of meetings with manufacturers of origin Croatian souvenirs, more meetings with restaurant managers to prepare top class authentic Croatian menus and creating Crosmopolit team. After setting up in Zagreb (capital city) we are now organizing work in Split (on Adriatic coast) and Dubrovnik. It is unbelievably positive to work with great people, to do “job” that I don’t consider a job and to make guests happy when they learn about our country over couple of interesting hours 🙂 Thank you for all the optimism, motivation and positive energy!

  • Christy @ Ordinary Traveler says:

    I think my moment was when I got my first extremely well-paid architectural photography gig or when I was published in National Geographic Traveler. My thoughts were, “This is only the beginning!”

  • silverboom says:

    We had a “heck, yeah” idea over Christmas, 2009.

    Unemployed, leaving Denver to head south to do who knows what, we decided to put together a tour of 50 national parks in an RV, and to find a sponsor to underwrite the whole thing. We created a 4 page marketing plan, with the route map, costs, promises of audience, photo and blogging content rights, the works.

    We were nuts. We’d never RV’d before, never camped. But I had proven photo and writing skills.

    The weekend after New Year’s there was a big RV show in Denver. We attended and shopped our business plan. We had to go back the next day because none of the senior management people were at the booths the first day. When we returned, almost everyone we had left a marketing plan with had read the document and had questions, or were very encouraging. One sales guy was considering sponsoring us personally!

    We met a VP sales guy with Coleman, and he told us that the only way to secure sponsorship was by going directly to the President and/or CEO of our targeted RV companies. He gave us the names and contact information for 5 CEOs. We knew then that we were going to make it.

    What was the surprise was that our sponsors turned out to be Mercedes Benz and Airstream, which came about a week later through a personal friendship contact. The whole trip was underwritten – the RV (Airstream Interstate on a Sprinter van base), the gas, the RV camp costs, maintenance, wireless connectivity, computers, and cell phones.

    From idea to sponsorship totaled about seven weeks, and we were on the road April 24. Picked up a brand new RV from Airstream’s factory in Jackson Center, Ohio. Toured 50 national parks in 217 days, covering 34,000+ miles. From Colorado to Texas to California to Alaska to Montana to the Dakotas to Minnesota to Maine to Virginia to the Florida Keys. We did it all. The adventure of a lifetime.

    “Heck, yeah!”

  • Becky Blanton says:

    I was homeless, living in a van in a Walmart parking lot, believing the lie that I was “just a homeless woman,” even though I was working full-time. I couldn’t afford an apartment on minimum wage. I was contemplating suicide (hard to hang yourself in a van), when a friend called to tell me Tim Russert was talking about me on CSPAN, CNN and The Today Show. (He had selected my essay to be in his book, “Wisdom of Our Fathers” the year prior – when I wasn’t homeless.) He was telling people my essay was what caused him to include a chapter on Forgiveness in his book. The next day I went into a bookstore, found the book, reread my essay and realized, “I was a WRITER!” not a homeless woman. Homeless was WHERE I was, NOT WHO I was.

    Three years later? I was speaking at TED Global 2009 courtesy of Dan Pink – because of my WRITING. Next month I’m launching the series of books I’ve always wanted to WRITE. But the moment I stood in the bookstore reading the book I couldn’t afford to buy to read the story I wrote for it…was the moment I knew.

  • Austin L. Church says:

    Two dates come to mind: April 17, 2009 and April 8, 2010. The former was the day I got laid off from my job as a copywriter at a marketing firm. I had $486 in my bank account and $6000 worth of debt from grad school. The latter date marked giving a check for $1500 to my dad and becoming debt-free. In twelve months as a freelance writer during the worst economy since the Great Depression, I had paid off all my debt, paid all my bills, and finally done something even crazier by starting a Roth IRA. Getting laid off was one of the best things that has ever happened to me. I now choose my clients, make my own schedule, and make significantly more money than I was before.

  • Andrew says:

    Reading this is all I need right now to keep going. Everywhere I turn I see people saying “don’t give up” – so I’m not going to! Life is too important to settle…

    Thanks Chris, looking forward to the book.

  • Adeea Rogers says:

    At first, I didn’t think I had anything to contribute to this story until you posed the question at the end and then it hit me. My example is small to some, but HUGE for me. I planned an event that I was unsure would be welcomed in my area. RSVPs were coming in slowly and seemed to inch up daily. In the last week of the event the RSVPs doubled. However I was skeptical, because you know people say they are coming and then don’t. Well, they all did…and then some! I ended up having at least 25 over the number I planned for and the event was a success. The 2nd one (last weekend) ended up having a wait list and I had to turn people away. I guess the moment I knew did not occur until the door opened and people started walking in and kept walking in. 🙂

  • Stephenie Zamora says:

    Awesome, AWESOME stories. Thank you for sharing these. For me I would say it was when a friend emailed me an extremely heartfelt email that showed how well she understood what I was trying to do and how much she believed in me. It’s not a huge win or sale or anything, but it was acknowledgment that I was on the right path. xo

  • Brooke says:

    I am typically such a nonconformist who hates going with trends. But I have to remind myself that sometimes, to have a successful business, going with the flow is the best way.

    I offer on-site Pilates and yoga classes and private sessions. An apartment complex where we do a few classes a week (and have for several years) was looking to shake things up somehow, as attendance had been stagnant. My business had also been stagnant, due to a work injury (contracting for someone else) that has taken two surgeries and over a year to fix.

    I immediately thought of trends and “outside of my business box” and hired a Zumba instructor for one of my classes at this client site. It’s been a great six weeks there, the residents love it, and this has been a fantastic decision.

    Lesson learned on my part: it’s OK to go with trends, sometimes. It’s also OK to not shoehorn myself into one category (mind-body fitness). It was a small risk, and it’s paid off well.

  • Teresa says:

    I didnt have one specific moment but world validations which lead me to realize that pursuing my life long dream of travelling for a year was coming true. First, my job reduced my hours so it made it easier to leave a stable “full” time job, next I was able to find a subleaser who could pay all my rent up front so I still had a place to come back to and finally I kept getting signals through other people. Finally, family validation, mail coming about travel shots, just little quirky things that made me realize the universe was telling me I MUST do what I wanted.

    YA — I leave in two months 🙂 I was so worried and stressed about making the real choices but I have learned when you do what you know is right for you the universe will validate it.

  • Molly says:

    I had a crazy little idea. I saw a post about making dresses for little girls in Africa from pillowcases. I love to sew, and I loved this clever re-purposing, and I really loved the humanitarian purpose. My church has a relationship with one in Liberia, so naturally I thought we could make these dresses for our next visit. I had set a goal of making 150 dresses in the 2 months we had until we needed to ship. The response was so overwhelming. To make a long story short, I was able to go to Liberia myself to deliver 260 dresses to orphaned girls, and I still had 120 pillowcases left over from the outpouring of donations. I am now in season 2 of my pillowcase dress project, and again, the people that are finding us, the support we are receiving is nothing short of miraculous. I had a vision a little over a year ago that I was scarcely bold enough to utter. Now my goals are even bigger and crazier.

  • marianney says:

    Alyzande, congrats! 🙂

  • Andrea MacDonald says:

    This is to Becky Blanton…thank you for sharing your story. I’m here in a diner eating a lunch I really can’t afford very depressed over the fact that I have to go back to computer consulting and giving up my dream of being the fiberguru.

    I just read what you had to say about you’re moment that you knew..and I realized something…while in the short term I may work at something, that doesn’t mean I am that something. Instead I am a fiberguru, I love to teach people to weave, crochet, spin, dye, knit and work with fiber animals….I may make my $ doing something else…but it isn’t who I am.

    Thank you! Thank you so much!

  • Kim Kircher says:

    Success is adding up these moments, one by one like a string of pearls. From doubt to confidence, back to doubt, then confidence again. Each one is a surge moving you closer to your goal.

  • Kate Courageous says:

    This might sound strange, but the moment when I knew that I would be successful is the moment when I decided that I was willing to work at my old job again, for awhile, part-time.

    I had naively had a “build it and they will come” mentality around working for myself, and a year into it, it was clear that that wasn’t happening, despite my working 60+ hour weeks to try and get some movement going.

    I had two health emergencies about two months apart, and had crappy private health insurance. Financial pressure was building.

    I realized that I could create so much more ease for myself if I simply worked part-time and built up what I was doing slowly.

    That moment was critical because it was a moment when I realized I was willing to do WHATEVER it took, even if one of those steps was the “uncool” and seemingly backward step of taking on some 9-5 work. Oddly, that was the moment when I knew that I was truly committed, because I was more invested in doing what WORKED than doing what made for a better story.

    Instead of waiting for someone else’s “Sacred Yes,” I simply created my own. I’m a lot happier–and my business is taking off!

  • Jenny says:

    Fantastic post Mr G….and @Deborah…don’t worry that moment will come, the tipping point ..between when you realise you can’t go back and you cross your fingers and pray for all your worth and leap…don’t worry success will come

  • Fiona Leonard says:

    Last week I stood up at the beginning of my book launch and asked if there was someone in the audience who had already bought a copy of my book. I asked the person to turn to the back page and read out the date written there – it was 9 July. 11 days earlier my book had been printed in the US packed in a box and shipped to Ghana, West Africa in time for my launch. I said to the audience that if anyone tells you it’s a terrible time to be an author, tell them they’re wrong!

    Oh, btw, I should have said my “self published book”, that I wrote in my bedroom/office in Ghana, had edited and cover designed in Australia and then printed/published in the US (all coordinated online).

    In that moment it all felt possible. At the end of the evening when I discovered that every single book had been sold…well that would have to count as a moment when I felt a bit of an inkling that yes I could in fact be a published author!

  • Bjorn Karlman says:

    Thanks for the encouraging stories Chris. I think one of my biggest moments of going from doubt to confidence would have to be when I finally received my work papers that would allow me as a Swede to stay in the United States. I remember I had 51 days left of legal residence before I’d have to deport myself:)

  • Mandy says:

    The moment I “KNEW” was when I received an email from a respected Art Historian asking me if she could use one of my images in a talk she was giving at the National Gallery in London. I had mailed her publisher one of my post cards, along with a letter, when I was in a group show in New York earlier that year, hoping the publisher would pass it along to her (but I didn’t even know if she would receive it). When I got the email from her a few months later, asking if I would allow her to talk about me and include my images, I nearly jumped out of my skin. I called my husband and we immediately booked our flights to London for the talk. A few weeks later, I sat in amazement as the art historian I respect most in the whole world talked about MY WORK at the NATIONAL GALLERY in London!!! It was a mind blowing experience and it all happened because I sent a piece of snail mail introducing myself!

  • Kyle says:

    Hey look, it’s me! How exciting!

    I can’t wait to read the book. I never really stopped and analyzed my story until your interview questions, Chris. Actually stopping to think about it has made me even more grateful and happy to be where I am now.

  • Amy says:

    I knew as soon as the man who I am a personal assistant for said, “You know, I’ve written a rambling memoir and I think it has the potential to be a pretty good novel, but it needs a lot of work and I just don’t know where to go from here…”

    I was confident that I could do it. When he said he’d give me a shot, I felt both perfectly calm and totally exhilarated.

    Before that moment I was floating along searcing for my true vocation, now I am a paid writer and “our” book is on the road to publication. Best of all, I have loved every minute of working on it.

  • Donna Carty says:

    It was when I heard that my application for a grant from UnLtd had been successful. If that had not happened, when two months later we were told that our UK work visas would not be extended, I would have left the UK feeling like my grand idea to foster home-grown textile businesses was a no-go. As it is, yes, we had to leave the UK, but I haven’t given up. I KNOW I’ve got a good idea, and if I keep looking for a way to do it, it will happen. If you want to help, keep Indonesia in mind, which encourages all its people to wear batiks on Friday to support their traditional textile skills. On Fridays, wear something made by a local textile artist.

  • Tristan says:

    Great post Chris and nice to see everyone’s moments. I haven’t had a monumental moment yet, but a small win for me was being accepted as a part-time Spanish teacher.

    I was a student at the time, and, after finishing the last course at the Spanish school, asked whether they needed any extra help with administration or curriculum. By coincidence, they needed help with teaching beginners (not admin, nor curriculum).. so I happily accepted and really loved teaching what I’d learnt. It was funny because I hadn’t asked about teaching roles, but they believed in me more than I beleived in myself. It was like going full circle within a month.

  • G. says:

    I think for a lot of people the moment they knew is one of adversity or pretty large change.
    For me it was being pretty broke, with a leg in a cast from a snapped achilles tendon, no job, no prospect of one in the future and delays on the book I was writing. Somewhere in the middle of that I decided I would die before I gave up on doing what I wanted.

    A few months later the book (a very specialised topic) was out and became one of the top 100 on Amazon in its category. I have survived for several months just on the income from that one book alone. In the last 3 months I have since written two more books, which do not have the same earning potential, but what I am sure of is that I can be a writer. Now I need to ensure I can make a decent living at it!

  • Chase says:

    As I am launching my own business soon, these stories are more than encouraging, and look forward to my own. I remember a moment like this when I ran my concert venue in Orange County, CA. A favorite band of the moment was sound checking for a sold out show, the lights were swirling around the empty room, and I sat on the floor taking it in, realizing it was the building I had dreamt of for years spinning around me.

    Thanks for sharing these stories, Chris!

  • Simply Investing says:

    Very inspiring!! I guess I knew even before I started my venture. It’s hard to explain in words the passion and energy I felt and still feel today. I really think success is a state of mind, achievement can be measured usually in dollar amounts.

  • GutsyLiving says:

    Was it “worth it,” and was there was a specific moment when they knew for sure they would make it.
    What great questions to get people to talk about themselves rather than the “yes” “no” questions.

    Thanks, Chris.

  • Shirley Showalter says:

    The moment I knew was the moment I held my grandson in my arms for the first time. I knew I wanted take a year of my life and become the “granny nanny” who cares for him while my son and daughter-in-law go back to work. That would mean moving to NYC for the year, renting our house out in VA, and finding an apt. close to our son’s. It would also mean the opportunity to explore NYC and write my book in a setting close to but different from the place I describe in my childhood memoir. I am beginning life all over again at age 63. My husband and I chose the Conestoga Wagon as the image for our marriage, and we have lived it.

  • Emilie says:

    I’m not sure there was one moment, but rather a series of “small wins” that each filled me with more and more hope- little glimpses into what’s possible. I actually log these moments in my small wins journal so I can see how far I’ve come and how much bigger the wins are getting. But in terms of one big moment? Maybe that’s still to come… Or maybe it’s already arrived. I’m not sure.

    Thanks for this, Chris. Wonderful, as usual.

  • Liz says:

    I love reading all these comments about what inspires people.

    I’ve had a few ah-ha moments myself. About 2 years ago my husband and I did something we had been dreaming about for a while; we purchased a home in the south of France with the hope of being able to move over there permanently in 5-7 years and travel freely around Europe.

    The first night in our new house was sort of an epiphany. We had done something that most people only dream of, and we did it without having won the lottery, without making a million dollars a year, and without being special in any way other than being determined.

    We knew to sustain the lifestyle we wanted to live, we’d have to eventually run our own business (and one that was flexible enough to allow us to live anyway), but we kept pushing that out further and further, afraid to lose one of our incomes.

    A series of events finally lead to me launching a small web design company early 2011.

    I was terrified at first; about running my own business, about getting clients, about making money.

    But now, 6 months later, I am putting down rent for my first office space. I have a steady stream of clients… and suddenly France doesn’t seem so far away.

  • Kyle says:

    Shirley, I love that you are reading this blog. You are a hip granny nanny and and your son, daughter in law and grandson are lucky to have you!

  • Richard says:

    Can’t wait for your next book.

  • Roxanne says:

    There is such beauty and power to these stories. Kyle is one of my favorite bloggers out there and I am so glad she is featured in this post!

  • Rich says:

    Thanks for this article, it is really inspiring. I love the fact that people can do what they love and do well from it to the point of being self sufficient for income.
    I believe that as we have evolved we have created many forms of slavery, one of which being the workforce and society….
    Well written!

  • Richy says:

    The moment i knew i didnt want to be in the workforce any more was the day i turned my first dollar working online. The entrepreneur inside me was screaming to be let out and i made the big decision to give it a go!

  • micheal says:

    I really think success is a state of mind, ,you would be correct on the top of giving up before getting that little bit of impetus you need to carry on and eventually experience success. well written

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