On Failure

On Failure

A few weeks ago, I wrote about my thoughts on success as part of the Common Sense Marketing newsletter. And while I don’t want to repeat what’s already been said, I’ll summarize for those of you who missed that email. Success is a very personal thing, and it’s important to be as clear with yourself as possible so that you can direct your actions towards achieving your own version of success.

(And yes, this is a subtle reminder to join my email list. Seriously – do it now, thank me later :))

But all that talk got me thinking about the corollary to success – failure. And then that got me thinking about just how spectacularly I’ve failed at different points in my entrepreneurial journey. If nothing else, I hope you get a kick out of these stories (in retrospect, some of them really are pretty funny…). But read them through – I’ve got some good old, “Full House” style, “Life lessons in 30 minutes” advice on failure that I think you’ll find useful.


My first failure (and yes, there have been many…) came from that classic childhood business model – the lemonade stand. I convinced my parents (early angel investors – thanks Mom and Dad!) to buy me lemonade, Dixie cups and a poster board to advertise my business. I tested different sugar-to-lemonade ratios for optimal flavor and even made an insulating cover for my pitcher to keep the product cool throughout the hot summer day.

Off to a good start, right? I was convinced I was on my way to a full closet of the Beanie Babies I was collecting at the time.

Wrong – total failure. Why? Because I lived on a farm in the middle of nowhere, where all of two cars drove by each day. At the end of the day, I’d made five sales – four to my next door neighbor who insisted she was “absolutely parched” and needed four glasses, and one to a very confused and very lost trucker who happened to drive by.

Lesson learned – all businesses need traffic, whether it’s lemonade stand customers or web visitors.


Next in my long line of business failures was a silk flower arranging business I conceived during a trip to Michael’s Craft Store while in college. The fact that I had absolutely no experience working with silk flowers (besides thinking they looked pretty in the store) didn’t stop me from buying $1,000 worth of wholesale flowers (a major investment for a college student!), launching a website and signing up to display my wares at a major bridal show.

As you can imagine, this was as spectacular a failure as it sounds like it would be. I had persuaded the organizer of the bridal show to have the models in the big wedding fashion show carry my creations down the runway – which backfired when the hot-glued-together petals started falling off one of the bouquets mid-catwalk. I wound up selling off some pieces on eBay and at a local street fair, but only finally resigned myself to donating the rest of the remaining inventory years later.

Lesson learned – you don’t need to be an expert before you launch a new business, but a little background education and preparation goes a long way towards preventing unnecessary expenditures.

Still not ready to let go of my entrepreneurial dreams, my last “real world” business venture was a personal concierge service my mom and I conceived of in the few months before I was set to graduate from college. We went as far as forming an LLC, designing a logo, setting our prices and services and building a website before I abruptly realized that, post-college, I was going to need a more stable source of income than a newly-launched business.

So I guess, technically, we killed this one before it even had a chance to fail.

Lesson learned – before launching a new business, know what your financial needs are and if you can realistically expect your business model to meet them in the timeframe you need.


Shortly after college, I discovered the world of internet marketing. And honestly, my failures in this realm have been too many to detail thoroughly here. But just a few highlights for you:

*Paying $700+ for an advanced course on advertising CPA ads via Adwords that I had no business buying. The $700 was a drop in the bucket compared to the amount of money I lost to poorly-designed Adwords campaigns.

Lesson learned – daily budget limits are your friend! (And, don’t spend more money on your business than you can reasonably afford to.)

*Buying an existing eCommerce website for $1,300 without fully understanding how much work goes into drop-shipping sites or how to market physical products effectively.

Lesson learned – start small and be clear on what exactly is involved before buying an existing business.

*Launching a membership site during the six month period in which I attempted to buy my first home and plan/have my wedding.

Lesson learned – don’t try to buy a house and have a wedding in a six month window! (And, be realistic about how much time you can commit to an ongoing project.)


But as much as it’s embarrassing sometimes to look back on all these failures, I’m also aware that without them, I wouldn’t be where I am today. It was the process of failing over and over again that helped me to figure out what I’m good at and where I should focus my attention.

You’ve probably heard the expression, “Fail Fast” if you spend any time hanging out around affiliate marketers. And while I totally agree with this sentiment, it’s not the full picture.

Failing fast for failure’s sake isn’t useful. If you don’t take the time to analyze exactly where you went wrong, what caused the failure, and whether it’s worth it to address the cause of the failure or better to move on to another idea, you aren’t going to learn anything from your failures. And if you don’t learn from your failures, you’re probably going to repeat at least one of those mistakes again.

This is where I’d love to hear from you. Any amazingly huge failures you’d like to share (and the lessons you learned from them, of course)? Or do you feel like you’re constantly making the same mistakes over and over again?

Let me know in the comments!

Image: Alex Jarvis

3 Responses to On Failure

  1. Jon says:

    “So I guess, technically, we killed this one before it even had a chance to fail.”

    hahaha…been there, done that.

    Sarah it seems we both were bitten by the entrepreneurial bug early. I could rattle on about many failed ventures and hare-brained ideas that just tanked.

    That Adwords dance probably left you sore for quite some time. Yikes.

    I failed trying to start a used car lot without my own lot, garage to inspect them, or a license to do it. Long story.

    Didn’t last long in the novelty t-shirt sales business when I was 19. I guess hanging out on the beach talking to girls was more exciting than pitching my tees with witty slogans.

    Stuffing envelopes scam. Need I say more?

    I could go on but this could seriously be a good post to write for me too. Thanks!


    • Sarah says:

      Hahaha – The used car lot without a lot, garage or license story sounds pretty awesome 🙂

      It sucks, but failure’s an important part of growing a business. At least now I can laugh at some of these things in retrospect!

  2. […] look back on in a few years and wonder what the hell you were thinking (seriously, ask me about my Adsense membership site…). Chances are you’re going to lose money on some of these “great ideas” […]

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