I post a lot of content online for 3 avatars:

  • I improve school leadership by upgrading habits, systems, and mindsets that optimize life.
  • I help small business owners produce high quality podcasts with little effort so they can focus on helping the world.
  • I liberate small business owners from the chaos of working in their business through a proven four step system.

My content is shared in the form of podcasts, articles on LinkedIn, articles here on Medium, and videos.

My podcast, Better Leaders Better Schools is consistently the most downloaded show for school leaders in iTunes 200,000 downloads since September 2015.

Although I work hard at being both transparent and vulnerable, I often worry that I’m like every other online persona …

Look at me … I’m awesome … my life is perfect!

My life is far from perfect and although I enjoyed amazing success this year, there are a number of lows points I experienced as well.

It’s tough to be grateful for those lows too.

They hurt.

But often, I realize that failure leads to wonderful wisdom and success down the road.

So below are my list of Top Failures from 2017.

1) NASSP Rejected Me.

NASSP is the National Association of Secondary School Principals and each year they facilitate a conference for all principals in the USA.

I spoke at last year’s event on productivity. The room was packed and literally people were standing outside and inside the lecture hall without a seat because of the content (and they wanted to see me). This was a cool experience because for the first time people knew me that I never met. They knew me because of my voice and because of the podcast. It was awesome.

In fact, NASSP used my picture from last year’s conference to solicit proposals for this year. With high ratings from 2017, the #1 podcast for school leaders, and 2 proposals submitted to speak, I thought for sure I would get a chance.


That’s okay, I probably needed the ego check.

I’m preparing myself for a NAESP rejection this year too …

Lesson learned:

NASSP didn’t target me. Don’t internalize rejection. When one door closes another will open.

What’s my next step?

Offer the same sessions via webinar and potentially reach more people (*added bonus … I can facilitate the webinar in sweat pants and a tee shirt 🤯😂🤦‍)

2) I avoided many tough conversations.

Like many people I don’t like tough conversations. I don’t like them mostly because they are uncomfortable and often they don’t go as planned.

It’s easier to avoid conversations that need to be had, but it’s not right.

As a leader people are relying on you to “show up” and part of that is addressing behaviors that are not welcome in a culture. Seth Godin once said in an online course I took of his, “You get the culture you deserve.


If that’s true, then the dysfunction I saw was a direct result to me avoiding the conversations that needed to be had.

I was a coward and took the easy way out.

Lesson learned:

If I am a leader, I have tough conversations. Seek out help if I need encouragement. Tell others what I plan to do for accountability. Prepare for the tough conversation and go into it with the intention of serving the other person.

What’s my next step?

Stop avoiding tough convos when they come up.

3) I chose easy and the “next logical step” instead of going “all-in” on myself.

For the 2016–2017 school year, I had a choice to seek a principal position or go “all-in” on Better Leaders Better Schools.

A year ago, I was still building my business and platform. I fell into the trap of what most people do and I thought that I needed more leadership experience in order to serve leaders via Better Leaders.

That wasn’t true.

If you speak with integrity and consistently; if you give, give, and give some more; it doesn’t matter who you are or where you come from.

People crave authenticity. People crave results and transformation.

I (wrongly) thought that people cared about my resume.

They don’t.

They care about results. They care about connection. They care that I care about them.

I always thought I would pursue Better Leaders full time, but my goal was to do that in 2021. I wanted a solid 5 years of principal experience.

How did I come up with that number? Who knows.

I most likely was just afraid to pursue Better Leaders full time. I learned a lot from this failure.

Lesson learned:

Always bet on myself.

What’s my next step?

I’m doing it. Although I’ve had many failures this year, nothing … absolutely nothing … has been more rewarding and energizing than living out this quote:

4) I spent too much time focusing on negatives.

Can you relate?

I don’t know if it’s a leader thing or just human experience, but no matter what I achieve, it drives me nuts when I make a mistake that could have been avoided. I also struggle with negative comments from others.

I can get 1000s of retweets, likes, and positive comments, but every now and then someone from #TeamHate decides to blast me publicly.

I struggled dealing with the hate at first and this is something I am learning to get better at which is important. As Better Leaders and my other ventures continue to grow, I am sure that I will attract more trolls.

Many individuals that inspire me offer the same advice, “Don’t read the comments and reviews … don’t respond to haters.” I started to act on this advice, but with my first hater I thought I would change them with logic and love 😳. Boy was I naive!

Lesson learned:

Stewing in negativity doesn’t help anyone.

What’s my next step?

Keep rockin’ the gratitude journal.

5) I didn’t help a friend as much as I should have.

In the summer of 2017, my friend Jaime Jay asked me to help him promote his awesome companies. We formed a deal that I would make a commission for customers I sent his way and I was super excited for the opportunity.

The problem is that I think I should have said “No” at the time. Not because I don’t care or I don’t have the skills, but because I was newly married, I made an international move, and I was busy growing my own ventures.

I just couldn’t find the time. I lacked capacity. If you’re reading this … sorry Jaime!!!

Slapshot Studios helps with:

  • websites
  • brading
  • chatbots

Bottleneck Virtual Assistants matches talented VAs with entrepreneurs.

Podcast Pilot is similar to what I do at No Sweat Media. We offer a no-nonsense, turn-key solution to busy professionals that know having a podcast is important, but they want someone to take care of audio quality, show notes, and distribution.

Castrly is a SaaS service that helps podcast producers (like me) manage workflow in an incredibly efficient way saving an incredible amount of time.

Lesson learned:

There are only so many hours in a day and despite having to potential to be good at something doesn’t mean I should do it.

What’s my next step?

Get better at saying “No.”

6) I ignored my true north and made decisions based on 💩 advice.

Last year was rough.

I actually have no idea how to write about this topic without dragging anyone through the mud. So I’ll leave it at that— it was a tough year and I followed the terrible advice from someone I should have been able to trust.

I acted on advice that should have helped me succeed, but I wasn’t savvy enough to notice at first it was actually meant to sabotage my efforts.

This was a huge failure and at the same time the best thing that happened to me all year. Because of this lesson I am now living out my life’s purpose in a way I never thought possible.

It didn’t feel great at the time, but I am really grateful for this experience now.

Lesson learned:

True north is everything and ignore people that are full of 💩

What’s my next step?

Forgive and move on.

7) I bought domains and didn’t move (much) on them.

In 2017 I bought domains for No Sweat Media and Danny Sunshine.

I have enjoyed tremendous success as a podcaster and I can offer those insights serving soon-to-be podcasters via No Sweat Media. I want to build a personal brand, inspiring and encouraging people to be their best so I bought Danny Sunshine too.

I barely did any work on those websites.

Not a huge failure at all. I’ve been swamped with BLBS content and clients, as well as referral clients for my podcast and business coaching.

I don’t need the websites since many of my clients come word-of-mouth … I’m so thankful for this.

However, I included this issue because I am quickly learning about my own limits in regards to what I can get done during a day. I am also learning what I should say “Yes” and “No” too.

I look forward to saying “No” much more in 2018.

Lesson learned:

Say “No” to more and be more realistic with what I can accomplish.

What’s my next step?

Say “No” to most new opportunities or at least have an idea of what to say “Yes” and “No” to before the opportunities present themselves.

8) I overslept and missed a great opportunity to serve.

I’m actually not a big fan of Twitter at all. I find it kind of annoying, but the fact is educators love Twitter.


We grab on to something and are slow to change. Educators tend to be pretty conservative and generally want to avoid risk at all costs.

So Twitter is where it’s at and since I want to grow relationships, meet new educators, and hopefully offer value through Better Leaders … I live on Twitter too.

My absolute favorite chat on Twitter for educators is #LeadUpChat.

Other great chats include #KidsDeserveIt, #PIAchat, #PrinLeaderChat, #EduGladiators, #Satchat #Edchat.

#LeadUpChat happens every Saturday at 8:30 am CST.

I was scheduled to facilitate a chat in the spring of 2017. I prepared all the questions and graphics weeks ahead of time.

I had it scheduled in my calendar.

I set my alarm …

And never woke up 🤦‍

This event was soooo embarrassing. I wanted to add a bunch of value to the chat talking leadership and maybe even grabbing a few new podcast listeners.

Which kind of hard to do when you don’t show up.

Lesson learned:

Set 10 back up alarms.

Just kidding … always work as a team.

Because I communicated with Jeff Veal (co-founder of #LeadUpChat) and done all the prep work, the chat was still a success … despite me not showing up.

What’s my next step?

Keep putting myself out there. Apologize and own my mistakes.

9) I wrote dozens of rejected articles.

I don’t want to list all the examples here, but I put myself out there dozens of times and faced rejection after rejection.

In fact, I didn’t get one article published on an online site besides my own in 2017. It’s weird because my FB live views and podcast downloads tell one story, but rejection after rejection from established educational groups are telling me another …

So what do I make of all this?

Either my writing sucks, I’m not communicating the value of articles enough, my content is not the right “fit” for the Big Dogs, or I’m operating in a different space altogether.

I’d like to get published in array of areas, but it really doesn’t matter. Through Medium, LinkedIn, FB, Twitter, Insta, my podcast, I have a big microphone and I plan on continuing to use it.

I don’t need a platform. I own the platform.

I choose myself and continue to impact school leadership on my own terms.

Lesson learned:

Rejection hurts. Also, there is a clash between new school leaders and the old. The established brands don’t have a clue on what is coming and they are not prepared for the future.

What’s my next step?

Thank you James Altucher. I am Choosing Myself.

10) I defined myself as an angry person and stewed in my own filth much too long.

For years I have mislabeled myself negatively. Generally, I am a peaceful and calm guy.

My favorite compliment last year came from my colleague Michelle, “You are the calmest person I know. And we need that so desperately here.”

That comment meant the world to me because it validated the inner-work I have been doing for years both through the guidance of a therapist and through what I do on my own.

I have really gravitated to meditation as a secular practice to reset. With my Mastermind clients, we read Search Inside Yourself last year. There were so many takeaways for everyone who read the book, but one of the BIGGEST takeaways for me — I am not my emotions.

Just like every other human on the earth, I experience anger, but I am not the anger I feel.

This was a transformational idea to expect because so often I get stuck. I replay the moment over and over. I bombard myself with negative self-talk, “You are so stupid.”

Big shoutout to Josh Spodek whose book Leadership Step by Step taught me to really pay attention to my inner monologue. Once I knew what was going on inside my head, I could change it for the better.

Lesson learned:

I am not an angry person. I experience anger it is an emotion; it is not me.

What’s my next step?

Meditate. Meditate. Meditate. And apologize when I act like a jerk.

In Summary …

I encourage you to consider your own list of top failures. These painful points in our personal and professional lives are awesome because they really are opportunities for learning and growth.

I challenge readers to make their own list. Keep it private if you’d like. Post in public if you have the courage. Reflect on the lessons learned and share the wisdom that came after each failure.

If follow this advice, feel free to email me your list or tag me on Twitter (@alienearbud) so I can share. The world needs you!

Let’s Connect!

If I can help you in any way please reach out.

Email: daniel@betterleadersbetterschools.com

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Host of the Better Leaders Better Schools podcast with over one million downloads 🚀