Lately, I’ve been feeling like failure is a necessary precursor to success.

Allow me to explain.

I’ve got 4 guest posts coming up in the next 4 weeks.

I set a goal to guest post on a new site every other month. One could say that I’ve achieved my goal for the next 8 (!) months. I also have my first ebook coming out on 5/24. Guest-posting and releasing an ebook are my two major growth strategies for this site, and it’s exciting to have them converging during this time.

Let’s set aside the fact that I should have set a bigger goal in the first place and look at what happened to get me to this point. Specifically, I want to share the string of failures that preceded the posts…as case-studies in how to turn failures into stepping-stones toward success.

As my friend Leo* once defined humility:  “I don’t know. But I think it helps…to not be afraid of your faults.” Likewise, I’d say this about defining success:  “I don’t know. But I think it helps…to not be afraid of your failures.”

I love writers who are honest about their failures. I love when people talk about about the emotional roller-coaster and tenacity-bordering-on-insanity it takes to live your dream.

Let’s take it post by post, going behind the scenes…

1. Everyday Bright: If at first you don’t succeed, try, try again. (Also, make an effort to meet people.)

Ever since I met Jennifer Gresham, I’ve been hoping to post on Everyday Bright. Jen’s standards are high, with good reason:  her work is amazing, and her readers are inspiring in their own right. So I set to work.

The only problem was, she rejected the first two posts I wrote for her.

Two strikes, baby. Before I went for my third attempt, I:

  • Thanked Jen for her patience. (She writes the nicest rejection email.)
  • Took a break from trying.
  • Thought hard about what hadn’t worked in each post. I realized that the first was off in tone, the second in content.
  • Thought about what Jen and I had discussed when we met, and chose my topic accordingly. This is where the importance of meeting people comes in. On the day I met up with Jen I was totally nervous, and I’d just come from a long day of work. It would have been easy to make excuses and not go, but I’m glad I seized the opportunity. Furthermore, the personal connection (prior to my submissions) facilitated a learning process, with second and third chances to get it right.

On my third try, I hit a home run. (Or at least a high fly ball into left field.) You’ll be the judge on May 24th!

2. Books Distilled: Encourage others in their dreams.

My best friend Brooke has been my writing partner ever since college. We’ve challenged and encouraged each other, and our writing is better as a result. So, when she told me that she wanted to start a blog, I was thrilled. I’d longed to share the world of online writing with her, and hearing the energy and excitement in her voice made me so happy.

What did I learn from the opportunity to post on her site?

  • When you support others, they may well offer you support in return. It felt very natural for Brooke to ask me to guest-post, because I’d been supporting her and rooting for her all along. I’m so proud of her for being true to herself.
  • When you start living your dream, you inspire others to go after theirs, too.
  • You remember those who supported you from day one. It matters to be there at the beginning. I’ll always remember my first guest post, over at Be More With Less. Courtney gave me my first chance, and I’ll continue to support her!

3. Tiny Buddha: One rejection doesn’t define your work.

“The difference between successful people and unsuccessful people is that successful people fail more.” (Martha Beck, Ph.D, The Four Day Win.) In other words:  successful people take more chances. It’s scary as hell, but it works.

A few months ago, I wrote a guest post for a contest. I worked on it for days, but it did not win. Three other posts did.

The rejected post sat in my drafts folder, unpublished, for several weeks. I thought about submitting it elsewhere, but it just didn’t feel right.

Until the day my friend Rachel sent me a post on Tiny I liked the post, so I explored the site. In a few hours I had a new draft of my rejected post ready to go. I submitted it and received an acceptance the same day!

Here’s the kicker:  the site I’d originally written the post for has a few thousand fans and subscribers. Tiny Buddha has over 100,000 Twitter followers alone.

Lessons learned:

  • One rejection means one person didn’t see the beauty in what you created. I tend to fall into the false belief that if one person rejects something I wrote, it must mean it’s not good enough. (And I’m not good enough…)
  • The shame spiral doesn’t serve you. When you feel yourself doubting your gift and your work, step back. Call a friend. Read a positive review, or look at something you’re proud of. Then, look toward the future.
  • Keep your eyes open for a different showcase. As it turns out, Tiny Buddha is a much better fit for what I wrote!

4. Undefinable You: Take small opportunities (because that’s how you move forward.)

Successful people seize opportunities, even small ones. Last week, I noticed that Dusti Arab, a writer I admire, was looking to meet up with readers via Skype. She tweeted her availability, and I took a deep breath and tweeted back.

As in my meeting with Jen, I was totally nervous to Skype with Dusti…but it turned out to be a great move. Not only did I get to make a new friend and receive some timely wisdom and encouragement, but I also received an unexpected invitation to guest post on Dusti’s new site, Undefinable You!

Lessons learned:

  • If you don’t reach out, you lose out. Guest posting on Undefinable You is by invitation only. If I hadn’t taken the time to talk with Dusti, who knows if I would have received that invitation?
  • Your heroes may be more approachable than you think. As Dusti told me, “I used to be so scared to talk to people I admired online. Now, I say, if they’re online, I’m going to talk to them. Everybody wears pants!”
  • Small opportunities lead to bigger ones. You never know what might happen around the next curve in the road.

My hope for you is that you will be an alchemist…transforming ordinary failure into extraordinary success.


*Names have been changed.

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  1. Lance May 12, 2011 at 1:07 PM - Reply

    I *love* the message you share here – about how failing is truly how we succeed. And it is because in failing, it means we’re putting ourselves out there, trying things, and (hopefully) connecting more fully with our true being.

    And your “failures” above are shining examples of how a failure can be flipped into something so much greater! Maybe I’ll stop saying failure and start saying “springboard to greatness”!!

  2. Brooke May 12, 2011 at 1:46 PM - Reply

    I love this post! It feels very timely as I’m getting ready to send out a story I’ve been working on. Additionally, it’s easy to get discouraged when you feel like you blog and blog and people aren’t reading! Thanks for the encouragement and the shout-out.

  3. Tam May 12, 2011 at 2:24 PM - Reply

    So true, so true…I think you hit the nail on the head with this one.
    I always think back to the time I was interviewing for part-time jobs after high school…just something to save up a little money to go traveling. My first interview was at Starbucks…and I was rejected! I was feeling so down on myself that I almost went straight home. Luckily at the last minute, I pulled myself together for the next interview that I had scheduled.
    When I got the job at Gap Kids I still had no idea how that would direct my future career and life. What started as a cash-flow assist turned into a great learning experience that pointed me in the direction of design and ultimately my current path, a BFA in Interior Design and my own design company! Looking back I always thank Starbucks for rejecting me, but of course it wasn’t so clear at the time.
    Thanks for your courage in sharing your failures and subsequent successes!

    • Caroline McGraw May 12, 2011 at 3:47 PM - Reply

      Great story ~ and a very cool connection! Thank you, Tam. I felt a bit of fear in sharing this post, but the affirmations have been amazing.

  4. Jen Gresham May 12, 2011 at 3:34 PM - Reply

    I’m so glad I got to meet you. You’re a lovely writer and person. Who wouldn’t want to be associated with you?!

    Instead of thinking of guest posting like dating (i.e. a rejection is personal), people should think of it like haggling in a market. The first deal may not pan out, there may be a lot of back and forth, but people who want to work together find a way or amicably move on. I think your story of the post that ultimately went to Tiny Buddha is a great example. Nothing wrong with you and your writing–that post just wasn’t a fit for the other site.

    Can’t wait to see what’s next for you!

    • Caroline McGraw May 12, 2011 at 3:49 PM - Reply

      🙂 You are so kind, thank you Jen!
      And very good point ~ I like the haggling imagery, & will keep that in mind for future posts.

  5. Linda May 12, 2011 at 4:28 PM - Reply

    Hi Brooke–

    I just flew in from Twitter. So glad to hear that you have a series of guest posts coming up–that is admirable and formidable, for sure:).

    I always think of Michael Jordan’s quote about getting cut from his high school basketball team as motivation when I want to hang it up. “I’ve failed over and over again, and that’s why I succeed.” That’s one “Rejection Highlight Reel” I wouldn’t mind having.

    Thanks for the inspiration, and congratulations!

  6. Linda May 12, 2011 at 4:30 PM - Reply

    I meant to write “Carolyn.” So sorry for the gaffe…UGH!

    • Caroline McGraw May 12, 2011 at 4:40 PM - Reply

      No problem, Linda ~ I’ll consider it a compliment to be mixed up with Brooke 😉 ~Caroline

    • Caroline McGraw May 12, 2011 at 4:42 PM - Reply

      Thank you Linda ~ good to see you here. The story is so fitting, too!

  7. Tanja from Minimalist Packrat May 22, 2011 at 3:48 AM - Reply

    I love this post Caroline. And it’s funny… because I’ve still only done two guest posts! You’re going strong with your goal of one a month and having 4 out in one month is incredible. I’ve had people ask me to do one and I’m too much of a slacker to get off my duff and do it. And, er, the truth, I always seem to get writer’s block when I think about writing for someone else’s blog.

    Thank you for writing this post. It reminds me to reach out more than I have been. Life’s gotten busy and I haven’t been able to do all my regular blog rounds lately, and I’ve definitely been neglecting twitter. 🙂 You’re my inspiration to get my butt back into gear.


  8. Caroline McGraw May 23, 2011 at 12:51 AM - Reply

    Tanja, you’re most welcome! Always good to see you here; glad the post was motivational for you. Looking forward to seeing more of you out and about 🙂

  9. Ali Manning May 24, 2011 at 6:24 PM - Reply

    What a wonderful post! I just came across your site via your guest post on Everyday Bright today. I love how you weren’t afraid to put your failures as well as your successes out there. That was so brave and inspiring. In the past, receiving just one rejection has shut me down and I stopped trying for months and in some cases years. I should just look at them as stepping stones toward where I need to go, rather than road blocks. Thanks so much for sharing your experience and wisdom.

    • Caroline McGraw May 24, 2011 at 6:31 PM - Reply

      Ali, I’m glad you’re here! 🙂 I know what you mean about the tendency to ‘shut down’ and hide one’s perceived failures (I definitely felt vulnerable pushing ‘publish’ on that post!) Thrilled to hear that you’re seeing stepping stones where road blocks used to be!

  10. […] posts lately…we have. This is the 3rd out of 4 consecutive guest posts. (If missed it, go here for the full story!) I think Monday’s post will be the last in the series, but 2 others are […]

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