On failure, Willy Wonka, and what every entrepreneur understands (that no one else does)

What if it doesn’t work out?

It will.

But what if it doesn’t?

It has to.

But what if it doesn’t?

I will make it work out.

But what if it doesn’t?

I wanted to smack him.

We were in a café in the oldest part of Madrid. Seated on a terrace, midway up a broad cobblestone staircase, red potted geraniums spilling from wrought iron balconies overhead, powerful Spanish sun on our shoulders, jasmine and olive oil scenting the air, and the ever present rumble of laughter and conversation that pervades a place where cars are an inconvenience, strolling is a nightly ritual, and people consider the plazas their living rooms.

I was blissful.

He was worried.

Nine months before, I had left New York City. Relinquishing my well paying job and terrific Upper East Side duplex (oh yes!). Forsaking my friends, my family, and my brilliant a cappella group (no, I’m NOT kidding).

Selling off everything I owned on Craigslist: my bed, my first grown-up couch, and the cool new flat screen just bought to replace the 14 inch tv that was laughed at by every date I had ever had. I had bade farewell to everything and everyone and moved to Spain.

After ages of wanting desperately, wildly, whole heartedly, to live in Madrid, after years of scheming to get a company to move me there, I had just seized created an opportunity.

And now, here I was, all by myself in Madrid.

Starting up the Spanish office of a tiny French company. A company that no one had ever heard of, with no real company website to speak of, in an industry that was brand new and completely unknown in Spain. Figuring out the market, strategy, client meetings, proposals, contracts, materials, procedures, plans, and ultimately, delivery of services-all were down to me alone. In Spanish, did I mention that?

I had bet everything on this. On myself. That I could pull this off.

And now, this old family friend had come to visit me in Madrid, wanting to know what would happen if I failed.

He wanted me to be realistic. He wanted to hear about my plan B, my back-up project, my pre-arranged fall back position.

Well, I didn’t have one.

And this was the thing he didn’t get: I didn’t need one.

Because there would be no failure. I would make it work.

Yes, absolutely, things would not go as planned, that was guaranteed. An idea wouldn’t be as good as it seemed, the market would be different than expected, the customers wouldn’t come, the project wouldn’t go as planned. But just as certain was that I would learn and adapt, figure it out and pivot.

I would not give up. I would keep working, I would keep on going and going till it worked out.

That’s what you do when you fully commit. When, instead of betting on someone else and their plans, you bet ON YOURSELF.

And another thing: having a fall back plan is a terrible idea.

My best friend had taken the leap into ex-pat entrepreneurship four years before, packing up her entire life in San Francisco, and moving to Paris to open her PR business. During her first years there, she had encountered a whole passel of Americans who were trying to make a go of it in Paris. And one by one, they disappeared back to their lives in the U.S.

Because here is the thing: they didn’t go all in. They had kept the apartment in Boston, taken a leave of absence instead of quitting, stored all their belongings instead of moving or selling them. They had a back-up plan in case Paris didn’t work out. And so they didn’t make Paris work out. Every single one of those people with a fall back plan FELL BACK.

So what am I saying to you?

There is no failure, not as long as you keep going. Going forward and sideways and slantways and longways and backways and squareways and front ways and any other ways that you can think of.

That’s right, you are a Wonkavator.

And you’re not going to plan a fall back position.

Because creating is hard. Going in a different direction than everyone else and doing it alone is HARD. And scary and frustrating and lonely. And that pre-arranged soft place to land when it gets tough would make it so very much easier to just quit.

You’re not going to cheat yourself by putting any of your time or energy into building a plan B.

You’re going to put everything you have, everything you are, into plan A, into what you truly wish to be.

And to those who ask: what if it doesn’t work out?

You are not encouraging us to be “realistic,” you are encouraging us to be scared cowed cogs in the machine less than we are.


Ready to shut down all the naysayers and start making an Extraordinary Impact? Find out how we can make that happen.


  1. Patti Pokorchak

    oh Wendy, I love your posts. They always make me think and laugh and keep on going.

    With my last name pronounced Poker-Chuck, I really related to “going all in!”. Life as a poker game, Texas Hold ‘Em, you only make the big money or lose it all by going all in. And really, why hold back? It’s that niggly 1% or 10% or 50% holdback that will make you fail.

    Given I”m starting again –I call myself a serial entrepreneur now and count 2/6 great successes but that’s all Kevin Harrington, King of Infomercials achieves, so that’s good enough for me.

    May all entrepreneurs be like the Energizer Bunny and keep on going and going and going…….

    Someone famous said ‘don’t have a Plan B’, so that’s why you have to make Plan A work!

    Thanks for brightening up my day and keeping me going……

    • wendy tells all

      Patti! Thank you sweetie! And a belated happy birthday-I hope it was dreamy. I am thrilled that that is what you get from my posts-because that is what I am trying for. Yay! It’s working!!!!!! I know you will make it work. Because you will keep going. Long may you ride, Bunny! (ok, apparently I have run out of writing mojo!) 🙂

  2. Liz P.


    Man I love your posts, I always feel riled up and energetic after reading them. <3!

    Also, what you said above reminds me of this: http://youtu.be/cITNveY-kig

    • wendy tells all

      Liz! Thank you, thank you! So now that you’re riled, what are you going to do?!?!?!?

      • Liz P.

        Argh, I’m just not sure! Decision paralysis is my doom, I swear. 🙁

  3. Alexandra

    OMG, now I feel like I should come out and say that I am a closet Lover of Plan Bs! 😉
    (I am not a poker player like my big sister)
    But I must admit that – although this is not a business example – I became an
    ex-pat because I had simply given up everything in my old life back home, convinced I
    would just keep going and everything would work out. So Wendy’s thoughts may be scary, but it’s the thing to do: It is the Will that will forge the Way.
    Keep up the inspiring words, Wendy!

    • wendy tells all

      Hey Alex! And, two kids, a husband, two languages, (how many countries now?), an amazing life (and soon to be biz) to show for it-I would say that going all in definitely worked out for you!

  4. Astrid Weittenhiller

    Oh Wendy, your post came exactly at the right moment. I finally quit my job to be a fulltime coach – without enough clients yet. But with a lot of good ideas and a slow pace to make it real. But I am feeling great! It’s not rational, but my heart is jumping with excitement.
    I have a Plan B – but I do not think about it. I do not want to! I want to shine and go on – no matter how…
    Thanks for encouraging me and please keep your fingers crossed!

    Hope to see you soon. Love -Astrid

    • wendy tells all

      Astrid, I am so glad to hear that-both about your terrific news and that I encouraged you. I am excited to see all the good things that are coming your way!

  5. Jasmine Cabrera

    So you are saying that I can throw the traditional “business plan” headache to the wind? That would take a huge load off my mental state right now.

    • wendy tells all

      Hey Jasmine! Hell yes! Let that traditional plan blow right away!!!

  6. ChangeAcademy

    Wonkavator! New most epic word ever.

    Totally with you on this one Wendy. Racing drivers keep their eye in the road, not the barrier… Otherwise you end up where you look.

    And of course, my personal favorite (with the inevitable sailing slant)- “storm the island and burn the boats”. No turning back now 😉 x

    • wendy tells all

      Love it! I have read that is how the conquistadors kept their minions from turning around and heading back to the old world when they got here. Not only provided no exit/fall back plan, so their only choice was to succeed (or die), but let the natives know how serious they were. (not that I’m lauding those murdering Spanish bastards TOO much).

    • Karen J

      “You end up where you look”!
      OMG – how many times have I told *other people* exactly that??

      Thank you, Amy, and thank you Wendy for holding the space here!

  7. Victoria

    I like this mindset trick. I can see how it can work. 🙂 #gamesandgifts

  8. Anita Kaiser

    I struggle with this all the time with parenting and when discussing my biz with my partner. No need for realism there is plenty of that everywhere I look….let’s make our little spot here the place where dreams are created! #gamesandgifts

  9. Audrey Groeschel

    I think I needed that very much. I have had a plan b in my head for a long time. If not a solid one, something to fall back on. I know I have read this before but this time? It really hit me. #gamesandgifts

  10. Gael



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