Dan Faill: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

Pirie Jones Grossman
Authority Magazine
Published in
13 min readFeb 28, 2021


Set aside time for yourself. And speaking of setting things aside, you are your best asset. If you burn out, you’re no good to anyone. Take time for yourself and recharge, because it’s easy to get caught up in all of the other tasks; and tasks will always be there. One of my favorite things to do is draw when my kids “commission me” to do art for their rooms. I crank up some 90s jams and break out the art, and can just “be.”

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Dan Faill.

Dan Faill is an accomplished storyteller and national speaker. Having worked for over a decade on college campuses, advocating for safe and positive student experiences, Dan now travels the country as a full-time speaker and consultant, engaging audiences in hard but needed conversations. Dan shares personal stories that engage and inspire others to be their authentic selves, and be brave enough to the conversations that matter.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

Well I can certainly do my best to give an overview and tack on some fun facts while I’m at it. I was born and raised in Wilmington, North Carolina. My parents were divorced so I was the lucky kid with two birthdays and two holidays to celebrate each year. I was a total latch-key kid and always did my homework and assignments early so I could watch Fresh Prince when it aired at night (remember those days before streaming?!). In high school I was a two-time national champion for acting (the category was “mime”, but we can talk about that later). I think I really started to come out of my shell while doing theater in high school. Mix that in with a communication studies degree from UNCW, and you could say I had a great foundation for storytelling and making others laugh.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I’ve gone through several favorite quotes, however the quote that still resonates with me is John Lennon’s “Everything will be ok in the end, if it’s not ok then it’s not the end.” I love that because I think too often we strive for perfection not progress. We compare our chapter one to other people’s chapter 20. When we feel that nothing is going right, it’s important to know the journey isn’t over. Being in that mess is our message. I’m a child of divorced parents and I am also divorced with children. Just because my marriage was over doesn’t mean it was the end. I’m thankful my ex-wife and I co-parent like rock stars and continue to do things as a family. Everything might not be perfect, and that’s ok, because it’s also not the end.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

I am unapologetically authentic — I think this is what helps me and hurts me with people: my mouth. In my close friend group, I have the nickname of “inner monologue” because I tend to say what’s on other people’s mind. I was told years ago that I’ve got a fairly snarky personality and approach to things. I think that comes from a place of wanting to be liked by others, so I tend to be the humorous one in the group. However, those that know me also know there’s a lot of heart underneath, and I try to be a present, engaged and caring person.

I am an advocate — I worked in higher education for almost 15 years and over time I was able to unpack my layers of privilege and identity. In doing that work I also realized I have a responsibility to lift up voices that have been marginalized or silenced. I make a conscious effort to support BIPOC/LGBTQ businesses and use my voice and platform to help educate and show up as an ally.

I like making connections — One of my favorite things to do is connect people. I’ve been told I have a random network, and I’m ok with that. I love being in the middle of a conversation and saying “you should totally meet so-and-so” and making those networks grow. It’s like playing Six Degrees of Kevin Bacon, but with personal networks. After all, people will be more invested in a random connection if there’s a common denominator, or someone that “vouches” for them.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

For 15 years I worked in higher education, most of which I served as the staff member overseeing the fraternity/sorority community. I enjoyed interacting with students and helping organization leaders realize their own potential, or challenging preconceived notions about tradition. I created leadership courses and retreats, met with inspiring students, as well as students having some conduct issues. In everything I did, I believed in creating a safe and engaging student experience. However the hours were very random on nights and weekends, and in some cases I would work a 36-hour weekend (or more). When you’ve got kids that’s not always conducive to being a present parent.

And how did you “reinvent yourself” in your Second Chapter?

People knew that I worked on a college campus and had the side hustle of a speaker. When I went full time speaking and consulting, I wasn’t getting great traction initially. Then another speaker friend told me I needed to rebrand myself as a speaker that has higher education experience. That mindset helped so much as I started my reinvention process.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

One day I finally woke up, on many levels. I was tired of working from a cubicle. I enjoyed the people I worked with, but didn’t feel fulfilled. I showed up for work on a Wednesday in late July 2018 and before logging in already felt exhausted and deflated. So during my lunch break I reached out to my speaking agency and told them in four weeks I was going to take the leap and be a full time speaker and consultant. After all, as someone who talks about failure and taking chances, it was time to take my own advice and just make the leap. My only regret was not taking that leap years earlier.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

For over a decade I was taking topics that were not fun (think risk management, alcohol, consent), and making them engaging for college students. Then I realized I could take that same passion for making hard topics engaging and impact more than just the students where I worked — I could impact others across the nation. When I finally allowed myself the ability to dream “what if” I found my passion and creative juices going full force. And once I finally got out of my own way, and had friends that pushed me, it was like an awakening of belief in myself coupled with a desire to impact as many teams, organizations and human beings as possible.

How are things going with this new initiative? We would love to hear some specific examples or stories.

My Second Chapter is so much more fulfilling, but it also has its downsides. I’d love to say everything is sunshine and rainbows, but when you’re a professional public speaker when a global pandemic hits, and there’s no more public, I went into a state of shock and mourning. Yes I’ve been able to do virtual engagements, keynotes, workshops, etc — but I miss the travel, I miss shaking hands and seeing people as opposed to zoom screens. On the other side of that coin, what I have noticed in this “new Zoom normal,” is that more people engage via chat and Q&A. Everything has its ups and downs, and I still wouldn’t change anything with my Second Chapter.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Hands down my friend James Robilotta. I’ve known James for years, but he and I got closer over the last few years, and when I launched into my Second Chapter as a full-time speaker, James was there to coach and cheer me along the way. However James is also that friend who is going to hit you with the hard question you know you need to ask yourself but don’t want to answer. I remember one time I reached out and told him I felt “stuck” — he asked me if I wanted a friend to listen, or a friend to help problem solve (that’s how great he his, because he wanted to show up how I needed him). After some sharing he told me “There are two types of lazy: one is lazy-lethargic, just hanging out and procrastinating; the other is lazy-overloaded, where you’ve got so much in your brain that needs to be done that it’s easier to just stand still because you don’t know where to begin. So which lazy are you?” That still hits my feels when I feel stuck or unproductive.

Can you share the most interesting story that happened to you since you started in this new direction?

Oh, there’s lots of fun stories and random things that have happened for sure; I think the memory that stands out the most was doing my taxes the first time being a solopreneur. I opted to use a tax company to help make sure I didn’t mess anything up. I was at a conference presenting to a room of over 400 people and when I finished, I looked down and saw that my return had been filed. Overjoyed and curious what I might be getting back, I opened the email to find out I was not getting a return, but owed…a lot. I emailed the company and finally got through to someone to discuss my sticker shock. By this time some of the attendees found me in the conference lobby, entranced in a phone call. As they tried to get my attention to say thank you, I was simultaneously being told I owed basically the same amount I made in my first job. Attendees could see my face drop. When I hung up, one person came over and put their arm on my shoulder and asked if I was ok. I had just finished encouraging a room full of people to be more open and authentic with each other. It was a habit to respond with “Yeah I’m ok, I’m fine” and without missing a beat he said “We both know that’s a lie because you just told all of us that there’s always more to being ‘fine’”. In that moment, I forgot about the IRS and money and everything else going on in the world, and we laughed, a lot. The impact about having conversations that matter was reflected back at me in that moment, and I’ll forever be grateful to that attendee.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I think we all struggle with being ourselves from time to time. I know I’ve got this little negative Jiminy Cricket that gets in my head, telling me things like I’m not good enough, not qualified enough, questioning every move and talking down to me. Or I’ll get caught up in the Comparison Olympics when I look at social media. And then I realize that I can’t compare my Chapter 1 to someone else’s Chapter 20. Each night before I go to bed I list my wins for the day, no matter how small. Because a small win and a big win are still spelled the same. This little practice of gratitude and reassurance helps me realize that my days are productive rather than just “busy.”

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I’m thankful to have curated a great group of friends and colleagues over the years. Any time I have (another) hair-brained idea, they’re my go-to group for “hey what do y’all think about…” And when you’ve got a group of people that will both challenge and champion you, anything feels possible. When I pitched the idea of quitting the comfort of a full-time job and being a solopreneur speaker and consultant, there was a resounding “It’s about time”, which always helps you know you’re on the right track.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

You never grow as a person if you stay comfortable. And too often we’re ok with just being ok. There are different ways to get out of your comfort zone. For me, I might start by asking a friend or two for their thoughts on something before moving forward. Having someone to process thoughts and ideas with is always helpful. And then there are some projects I throw caution to the wind and just cannonball into the deep end. For example, I reached out to another speaker and randomly pitched the idea of creating a mini-bootcamp for people who want to be speakers help craft their story and get paid. Her enthusiasm matched mine and we took the leap — within a week we had a website, hired a media manager and are rocking registrations. Sometimes it’s timing, sometimes is a support group; however I never want to be complacent or comfortable again.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

  1. Be intentional with your time. Too often I would hear people talk about “work/life balance.” Call me a cynic but I don’t believe in balance — to imply balance implies things are equal and weigh the same or take up the same amount of time. Any human being knows that’s impossible. I think it’s all a question of priorities. So where will you intentionally focus your hours in the day?
  2. Connect with others. As human beings we long to belong. When you work from home or are a solopreneur, it’s easy to feel isolated and alone, especially in a global pandemic. I miss walking into my co-working space, starting up a convo with a stranger on an airplane (yes, I’m that guy), or just meeting people at events. However, there are still ways to connect with people. Zoom and Facetime as technologies have existed long before the pandemic. So find ways to connect with friends. Put yourself out there for a conference presentation or find a local club or organization that resonates with your interests.
  3. You will fail, and that’s ok. Failure has a bad rap. I grew up with the last name Faill, so you’d think I would have embraced it years ago. However now am able to see failure as the best possible thing to happen to me. Failures are intentional learning lessons. Sent that email that had a typo? Whoops, won’t do that again! Missed the flight to a speaking engagement because your ride share was moving like a snail? Now I’ll listen to my dad’s old advice when he said to get to the airport earlier! We’re human beings, failures happen to us all.
  4. Set aside money for taxes. Speaking of failures, don’t do what I did and forget to put aside 20–30% of your income for taxes. As an Independent Contractor/1099 gig-pay, it’s easy to allow yourself time to celebrate those paydays. But be a squirrel and put away some of your hard earned acorns for Tax Day.
  5. Set aside time for yourself. And speaking of setting things aside, you are your best asset. If you burn out, you’re no good to anyone. Take time for yourself and recharge, because it’s easy to get caught up in all of the other tasks; and tasks will always be there. One of my favorite things to do is draw when my kids “commission me” to do art for their rooms. I crank up some 90s jams and break out the art, and can just “be.”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

In a time when social media and technology has the ability to connect us more than ever, then why is there a loneliness epidemic? I want people to feel more connected, which means we have to move beyond “fine” or “busy” and actually be curious about one another. Everything we do, from work to family to relationships to friendships, everything has the foundation of relationships. I want to inspire a movement for people to be brave enough to have the conversations that matter.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

Hands down, Dr. Brené Brown — she can even choose the meal time! As someone who also works on creating vulnerable moments with audiences so they can have better conversations, I would be enthralled to bask in the presence of the creator of the authentic vulnerability movement we find ourselves in.

How can our readers further follow your work online?

I am on the interwebs at www.DanFaill.com and am @DanFaill on all social media channels.

Thank you so much for sharing these important insights. We wish you continued success and good health!

Thank you for the opportunity to engage with you and your readers. If there is anything else you need please let me know!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.