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The UN-conventional


You tried something and it didn’t work. How to embrace failure so you can try again and again

Aug 08, 2023

We get the message to not make the same mistake twice. In marketing, this is a mistake. Get comfortable with the feelings that come with failure and fail as many times as you need to make something work.

No one was there. Food for 200 laid out on beautiful platters. I’m in my ‘expensive’ Ann Taylor Loft outfit that I wore 3 days a week because it was the only one I owned professional enough for my role in sales.

I’d spent two weeks inviting all the new condo owners in downtown Denver to this event at the upscale athletic club where I worked. My goal was to get 200 new leads and sign 2 new members. And no one came.

I’m looking at my boss, who I’m sure is adding up all the dollars I spent on this event and I’m wondering if she will fire me now or tomorrow.

Luckily my boss and mentor was the magnificent Brenda Abdilla. She laughed, put all her own anxiety aside, and said “How can we do this better next time?”

The next time was a huge hit. We evaluated, and got creative. We made it an art evening with local talent. We asked ourselves how can our marketing event benefit more people? The next event recovered all the money from both events in membership referrals and became a regular part of our marketing strategy.

"There is no innovation and creativity without failure. Period." - Brene Brown

“There is no failure except in no longer trying.” - Chris Bradford (shout out to my ALG friends!)

"Many of life's failures are people who did not realize how close they were to success when they gave up." - Thomas Edison

The celebration of failure has been big in the entrepreneurial world in the last decade, but in my experience, most people and organizations aren’t walking the walk.

Instead, we get the message to be smart and not make the same mistake twice. Try things and then stop doing them when they don’t work. This way of thinking is a mistake, especially in marketing.

Keep going. Be ready for the feelings that come with failure; be willing to fail 10 to 100 times before you quit and try something else.

Here’s why:

You don’t do anything well the first time. If you are trying lots of things but not getting really good at one, you will start thinking “Nothing works!”

How this might be showing up in your business:

  • You posted a few times on [fill in social media platform], but it took so much time to create the content and no one even responded.
  • You sent out an email or newsletter and only 3 people opened or clicked on the link.
  • You boosted a post but didn’t see huge engagement.
  • You had an event but no one came or no one bought what you were selling.
  • You put up an online store but sales were dry.
  • You tried some paid advertising but didn’t get results.

Now, here's what to do:

Step 1:

  • List all the marketing/sales activities you’ve tried in the last 3 years.
  • Choose 3 to focus on for your next round of activities.

Step 2:

  • Give yourself some kindness and compassion, like Brenda did for me. Shame, embarrassment, guilt, and disappointment are normal feelings when you’ve failed. Not being scared to feel these feelings is the key to not quitting. Feel them and then talk to yourself like a great friend or mentor. It’s ok. Let’s try again because the world needs your work.

Step 3:

For the 3 you're focusing on write out:

  • What worked?
  • What didn’t?
  • What could you do better or differently?
  • What constraints can you add to make it more creative, valuable, and less expensive or time-consuming?

Step 4:

  • Now choose one (only 1!) to try again.
  • Do it 10 to 30 more times and try to improve every time. Get some real data.

Here’s an example of what trying a marketing activity again might look like in real life.

Let’s say you sent an email to a business or someone you wanted to collaborate with, but they never responded.

Maybe your ideal customer has recently bought a house so you reached out to a local real estate agent to see if you could collaborate, but they never wrote back.

Here’s what trying 10 to 100 more times could look like:

  • Send an improved email to 10 agents.
  • Stop by or call each of their offices and talk to whoever is there aka “the gatekeeper”.
  • Send a second email but improve it based on the info you learned from “the gatekeeper”. Offer more value or solve a problem for the agency.
  • Pause and reevaluate. Any collaboration yet? Still crickets? Change the offer again. Make it sweeter and easier for the Real Estate Agent. What can you do for them that is win/win and makes their job easier? Send a series of 5 emails to 30 more agents. Call them again.


If you contact 100 agents with 3-5 different offers to collaborate and still no takers, it’s time to try a different marketing idea. But I promise you’ll have made progress in selling your product to your perfect customer and created some brand awareness with 100 people who are in direct contact with your ideal customer.

Did you have a disappointing event, like me?

This one is common and what I’ve learned is events are often poorly attended the first few times OR they are wildly successful the first time but fall flat the second.

This leaves people feeling frustrated. But let me tell you: events are the bomb! Do them. Try them again. Online or in-person, events are a great marketing tool.

Even if no one shows up.

Think about that. It doesn’t even matter if no one comes to your event. It still gave you a real reason to get out there and talk to people about your product. I have often seen a boost in sales after a “failed” event.



Few warnings:

#1 Don’t spend a lot of money when you’re still in the learning and testing phase.

As soon as you know you're getting sales from your marketing, then you can put money behind it. Until then, be scrappy. How can you make something special without a lot of money or even time?

This is how I turned the flopped event into a successful one. At the first event, I dropped 2000 mailers at condo buildings, booked a caterer, and hoped it would work. These were cold leads and all I offered them was food. I didn’t really figure out what would be valuable to them.

For the second (successful) event, I went to the local art district and door-to-door invited artists to an evening where they could display and sell their art to our club members. We branded it an evening of Art & Wine. We sold tickets to cover the cost of the food and wine and made it exclusively for club members and their guests. This made the event look more desirable and valuable to our ideal client.

It was win-win-win all around, the members loved it and essentially sold memberships to their friends for us that night. The artists were also thrilled, they sold art and made connections.

#2 Don’t blame circumstances.

People don’t have money. The economy is bad. People are busy. It’s raining. It’s sunny. It’s a Tuesday. It’s the algorithm.

You need a lot of real data before you conclusively prove any of these and you’ll never get the data unless you keep trying.

The reality is shit happens, the economy dips, people are busy, pandemics hit. You can’t control any of that, you can only control if you keep trying or not. In every bad situation there are people who still thrive and succeed. You need to keep going and get more data to find the way to sell to your ideal customer.

#3 Your beliefs and fears are not facts.

I’m just not good at this. People will think I’m pushy or salesy. I don’t have time to try this again. Watch out for these. These are not serving you. They have everything to do with you and not how good your product is. But that will have to be another blog…


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