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Learning from Failures (and Wins) to Create More Success in Your Business

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For the past two weeks, we’ve been discussing the importance of approaching your work with a scientific mindset and using experimentation to learn and grow in your business. This is so you can avoid panic and stress, and so you can eliminate all unnecessary pressure as you put new ideas out into the world.

Today I want to marry these two ideas so you can learn from failures (and wins) to create more success in your business. You’ll see how to analyze your results so you can make intelligent changes to your ideas (however fantastic or not-so-awesome they turned out) and make them more fantastic and awesome next time around.

My First Big Failure

As I told you before, my first product was a total flop. One purchase after hundreds of hours of work left me rather heartbroken.

But as you’re learning so far, the important question is: What did I do after this failure?

Did I investigate what happened?
Did I exhaust every sales option?
Did I troubleshoot it from multiple angles?

Unfortunately… no. Instead, I threw in the towel without another thought. In hindsight, this was a bad idea. But at the time, I didn’t know there was an alternative.

Here’s the good news: You don’t need to make the same mistake I did!

Instead, you will don your scientist’s hat and start investigating.

To guide you through that process, here’s a list of questions you can use, either to recover from a little flop or repeat a big win.

Question 1: Before you do anything, have you reframed any failure thinking?

First, make sure you’re head is not full of failure thinking! This is step number one, and we talked about it a few weeks ago.

Always start here. Failure thinking will inhibit a successful scientific investigation!

Question 2: Did you put enough effort into marketing?  

One of the biggest mistakes I see newer entrepreneurs make is not putting enough effort into their marketing.

When I was first starting out, I had no idea how much time, brainpower, and sweat went into things like writing a sales page (I now spend upwards of 40+ hours while downing a cup after cup of coffee.), finding the perfect email headline (I lose handfuls of hair in the process.), or crafting every single word of a killer sales email (I can spend 5+ hours and drink a gallon of kombucha, something I strongly suggest you don’t do.), among a million other little details I’ve learned since.

Here are some things to consider regarding your marketing efforts, as you investigate your business hiccups and freshen up your big plan. Have you…

  • Put care and thought into every single word on your sales page and in your sales emails, making sure you’re speaking the language of your customers and demonstrating the life-changing value of what you offer, as seen from the perspective of your customers?
  • Given people a deadline to sign up? (And has that deadline passed?)
  • Used clear sales language and a specific call to action on your sales page?
  • Told your list at least 3 times with thoughtfully crafted emails, headlines, and calls to action? These should be dedicated emails, not off-hand mentions in your weekly email’s introduction or article.
  • Referenced your offer in at least 3 separate blog posts?
  • Mentioned your offer on every social media channel you’re active on at least 5 times each?
  • Personally reached out to people you know via email to tell them about your offer?
  • Asked your friends, past clients, supporters, and fans to help you spread the word and given them drop-dead-easy-to-follow Tweetables, Facebook posts, graphics, and email scripts to use?
  • Built your list to a point where you can hit your sales goal? (Conversion rates are 1-5%, so hopefully your list has a few hundred people or more on it.)

Question 3: Have you outlined and executed at least 7 backup plans?  

When you really want something to work, you’ll go through plans B, C, D, E, F, and all the way to Z if you have to. Tweet that!

For example, when I launched Make It Work, I used a scientist’s mindset as I was crafting my sales plan. I created seven back-up plans, because I wanted to sell out the program! Beyond the obvious sales page and sales emails and social shares, I had a list of many other ways I was willing to market this program to ensure it filled. (Fortunately, it sold out with just one email, so I’m saving those secret backup plans for my next launch.)

Whenever I want something bad enough, I always make seven back-up plans to increase my chance of success. (I’m rather determined that way!)

Question 4: Did you talk it through with others?

When an experiment goes awry, don’t sit alone in your office and try to sort it out all by yourself.

Enlist support from colleagues, your mastermind group, a coach, or someone besides yourself and your dog. If you haven’t talked through it with other people who have insight into your work, go do that – pronto!

We’re so invested in our own work that we’re too close to see where the issues lie. Others can often see what we can’t. Find folks who will be honest with you, and get all the outside perspective you can.

You can always use questions 2 and 3 to guide your discussions with your supporters if you need a framework.

Question 5: Do you really want it to be successful?

I realize this question may sound strange! However, entrepreneurs are far from immune to blindly self-sabotaging their dreams. I want you to inquire: Do you really want this sale to go through? Really?

I’ve known people who have said they wanted to make their business work, yet no matter what they did, nothing was clicking. They’re in tears over their lack of success, and a year later finally confess that they don’t really want this business. They had something else in mind. Oh, nelly!

There’s no time like RIGHT NOW to get honest about what you REALLY WANT in your business. Because if you’re out there creating something you don’t really want, it might not really work!

Question 6: Okay, you want it to be successful. How badly do you want it?

If you’re clear that you really want this idea or this business to work, excellent. Along the same lines as the seven backup plans I covered in question 4, getting what you want requires gumption.

Spirited effort and creative resourcefulness should be your go-to tools whenever you’re doing something new. Sort of how my friend Anna Kunnecke pulled off an amazing, seemingly impossible feat this past summer. You must read about it after you finish reading this post. She cracks me up (and inspires the heck out of me)!

Knowing When to Say When  

Now that you’re equipped with the essential questions to assess your failures (and wins) so you can make sure you’ve done everything to reach your goals, you’re probably left wondering…

How do I know when I’ve tweaked my idea enough times (without success) to put this idea to bed? How do I know when I’ve put in enough effort to know that my particular concept just isn’t going to work?

Even more challenging than “failing” in the entrepreneurial world is knowing when to close the book on something that just isn’t working.

And this is exactly what I’m going to cover next week: knowing when to call it quits. Because let’s be honest, sometimes ideas just aren’t going to work (and that’s okay).

It’s Your Turn, Dear Scientist

As always, I want to hear from you!

Is this idea of experimenting and tweaking something you struggle with in your business? Or does it come naturally to you?

Have you ever launched something and had it flop, then found ways to tweak it to success?

Do you have any other ideas or questions that could help business owners like you analyze successes and troubleshoot failures?

I can’t wait to hear your stories and experiences in the comments below!

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{ 24 comments… read them below or add one }

1 Angela

I’ve always been into finding ways to improve myself. However, when it’s come to my work (especially trying to figure out why people aren’t rushing to buy a certain something) it’s a different story. I love this blog post series – it’s helping me see how analyzing what’s not working at work is critical – and doesn’t have to be so scary!

Without a doubt, using your questions above would have made big differences in certain products I’ve created in past. Another question I’d add:

Is there something going on in my life that’s draining / distracting / keeping me from being at the top of my game?

I’ve experienced how stress in your personal life can have quite an impact on everything else you do: energy level, ability to focus … and just your vibes in general (which I think plays a huge role in what we’re able to accomplish). Acknowledging and addressing – so important!


2 Jenny Shih

Great addition, Angela! We certainly can have things going on in our lives that distract our attention and energies from launching something. That’s definitely something to consider.

Hoping this list and all of the questions help you the next time around!


3 Lacy

Really appreciate the marketing “checklist” in step No. 2. It’s hard to know what’s “enough” — but it looks like I haven’t even been doing the bare minimum! Thanks for that!


4 Adrianne Munkacsy

I’m with you, Lacy! I would’ve paid for that goldmine of information!


5 Jenny Shih

Glad you like it — enjoy (for free :-) )!


6 Shae

Agreed. I’ve got this list in Evernote now.


7 Miriam Ortiz y Pino

Great post and very timely as I’m preparing to launch a few things this year. Back up plans are good.


8 Alison Elissa Cardy

This is one of my favorite posts of yours Jenny! As you and Lacy noted the steps in question #2 are absolutely critical and often unknown to new entrepreneurs. It takes a lot of behind the scenes work to pull off a launch.

This post jazzed me up about taking another look at a recent launch I did.

A big aha that came to me recently is that there are subsets of reasons why people may be stuck in terms of career. In fact, I counted eight DIFFERENT common scenarios! My launch and program were trying to target all of those people, when in actuality doing more targeted marketing to a specific scenario would likely work better. Still thinking it through, but, as always, thanks for the food for thought and handy action steps!


9 Jenny Shih

Thanks for the kind words, Ali! I’m thrilled you found this useful.

What a great aha you had about your last launch. 8 different subsets is interesting! You can market to all of them at once; to do so you’ll want to call each one out in the marketing so you know they are “seen” by you. And, you could also narrow it down. Heck, run an experiment to see what works best for you and your people! :-)

Keep trying! I KNOW you’ll make it happen!


10 Jennifer Kennedy

Great food for thought!!

I’m soon launching a product, and these questions have my mind spinning with ideas.

One thing I’d like to do prior to the large launch, is to open it up to a few beta testers. I’d like to take the feedback from this small group to use with the marketing portion. Hopefully, this will give me enough feedback to tweak not only the content, but also wording on the sales page and emails that I send out.

Really, if at first you don’t succeed, analyze what you did, and then try again! That’s going to be my new launch mantra! :)


11 Jenny Shih

Testing an offer with a small group is definitely a great way to get feedback on your content and make sure what you’re doing gets great results. Good going!

I’ve got a post coming out in early spring with questions to ask your past clients and program participants to find their exact language. I used them when I was preparing to market Make It Work and it was helpful and insightful. I learned a lot about what they were thinking (in their exact words of course!) and how to more effectively reach the people I love working with most. It helped tremendously when I launched Make It Work. Watch for it!

Good luck to you!


12 Maria

Hi Jenny,

What you said about really wanting to be in this business was super insightful! Too many times we focus first on what we think we should do, and then on what we want to do. And that’s how it becomes complicated…


13 Jenny Shih

So true!


14 Marsha from


My goodness!!

This is AMAZING.Thank you so much. The marketing basics checklist is UNREAL. But the whole page – au!

THANK YOU. I am going to bookmark this page and refer to it again and again.


15 Jenny Shih

Practice. Experiment. Play. Try. Try again. Try a third time a new way. And most of all, never give up.

Especially you because you’ve got MAD SKILLS!!! :-)


16 Hanna Cooper

Jenny, you mind reader!

This series is totally kicking my butt. When I launched my first teleclass last spring and got crickets back, I really crawled in a shame hole. “Nope, I can’t do that.”

What a load.

At the time, I embraced the “learning” of the flop (or so I thought), but reading this makes me realize I didn’t examine all the nicks and cracks in my plan to wring that sucker dry. Now, maybe 8 months later, I think I’m ready – because I’m done taking it personally.

Thanks, Jenny.


17 Jenny Shih

Love that you’re embracing a re-do, Hanna. You have such great work to share! Cheering you on to go for it again!


18 Laura

I love this, Jenny!! I took notes under the header “when a launch isn’t working” and I will be referring to it when I relaunch my group program that didn’t get any signups last time. After doing some investigative work, I know why it didn’t go well and am clear that it was my fault as well. And that means I know some ways to make it work better next time! Thanks again for this!


19 Jenny Shih

Excellent, Laura! Keep up the good effort, keep trying, and keep experimenting. Remember to create seven backup plans before you launch. Go through the above list to get the “minimum requirements” then get super creative on how else you can spread the word.

I have a friend I was helping last week with her backup plans. (Mastermind buddies are great for brainstorming ideas.) She walked away from our call with a bunch of novel ways to market it that she hadn’t tried before. And more awesome than just having the plans themselves, having the plans boosted her confidence tenfold that she could pull off this big new thing. Grab your friends and brainstorm. Your launch will thank you.

Sending good launching vibes!!


20 MamaRed

Fantabulous stuff and boy, do I “get” that I didn’t market enough. True confession: that HAS been my weakness and understanding this is helping me make changes. Not to the point of success where I envision being in 2014 AND a huge ah ha came from a conversation about someone who was confused (dammit) about what I did. All of a sudden he said “jeez, everything you do improves the ROI…why don’t you claim that?” Then I realize the fear in the pit of my stomach as I work through that one. That IS was systems, proceses, strategies, plans and all that do. Why I wasn’t claiming it? Well, that’s another whole novel!

Laugh Lots, Love More!


21 Jenny Shih

It’s fun to read your personal aha’s MamaRed as you continue your story in the comments of this blog. I can see the openings, realizations, and breakthroughs your having. Your persistence is admirable! Keep learning, trying, experimenting, and committing to yourself to make this business work. I’m cheering you on!


22 MamaRed

Hey there Jenny…thanks so much for your encouragement. Even tho’ we don’t know each other on a personal level (and would LOVE to change that), I love what you’re about, how you’re sharing and well, you!

I’m meeting so many woman who are struggling with confidence, clarity, health issues, money issues. My mirrors and each is helping me take my next steps.

I also got some clarity on why it scares me so much to claim that what I do improves ROI and profits. EVEN tho I’ve saved some big companies thousands of dollars in their content creation realm and processes realm. Goodness, this has been a long journey, would LOVE to say I got this stuff before my ass was against a brick wall and since that would be a lie, well, I’m gonna own up, put on my big girl panties and keep on truckin.

Rock it darlin


23 anna long

Thanks for sharing Jenny I LOVE your somewhat hard-deaded approach to all this. When you have 7 backup plans…you mean business! I love it! Plus, I feel like there are so many people out there trying to convince people that all of this is easy…and in reality, it takes work and tweaking. I think most of us have a “failed” launch under our belts to learn from. I also love that you address whether people really want it or not. I honestly juuust got to the point where I wanted to launch my first group (even though it was on my to-do list for a year). If I had tried a year ago I wouldn’t have succeeded because I wasn’t actually ready.


24 Jenny Shih

You’re absolutely right, Anna! 7 backup plans does mean business — and if we want to create results, that’s how we git ‘er done! :-)

The whole idea that this is easy is such hogwash! I had a good laugh about that a few weekends ago at my first business retreat. One of my former coaches was there to speak and she reminded me all of the trials and tribulations I went through to get here. It’s not easy. It’s not fast. But it is possible. And making it happen requires upsets, failures, hiccups, and speed bumps. When we can learn to get through and past those, we will find success on the other end. I know it because I see it in my clients!

Good luck with your group launch. Sometimes those year-long to-do’s don’t get done until the timing’s perfect. Sounds like it’s ready now. Go for it!!


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