Rob Gregory Photography

Rob Gregory Photography

Hello and welcome to my 30 day challenge. Here I’m posting a new video every day for the final 30 days of my 30s. I’m sharing learning lessons and insights from my unique experiences so far.

The videos are short and succinct. I hope that you enjoy! I welcome your feedback, thoughts, suggestions and ideas regarding this project.


Tony Esteves


Day 21 – Manage your debt. Don’t run away from it.

Few people get to go through life without experiencing some form of debt. Some people live their entire lives in debt and it can be incredibly stressful. One of the most important lessons that I learned in my 30s was how to manage and overcome debt. I can’t stress enough to anyone who is feeling overwhelmed by some kind of debt that it IS manageable, but you have to learn how to manage it.

Today’s lesson?

Manage your debt. Don’t run away from it.

Day 22 – We Should Know Each Other.

Last night I had the privilege of attending the 149th “We Should Know Each Other” event in Calgary. Mark Hopkins has been generously hosting these parties in his apartment for the past 7 years! He has brought literally thousands of people together with the intention of just getting to know each other. Imagine that?

We spoke about this in today’s first video (created last night) and I believe that he’s done a wonderful job of creating this opportunity for so many people to create unexpected connections. Check out Mark’s TEDx Talk or join the Facebook group for more detailed information about

Than you Mark for all that you have done and I look forward to seeing how WSKEO evolves.

Today’s lesson?

We Should Know Each Other.


Day 22 – Bonus Video – Talk To More People

My longtime friend and room-mate, Rob Gregory and I have a few things in common. We both really enjoy meeting people, like helping people out, and enjoy speaking to people in situations when it’s unconventional. The closest place that I could find for this was the elevator in my building.

While most people tend to look down, or up at the numbers or out the window in elevators, Rob and I make a conscious effort to speak to people for those brief moments. There are a number of reasons for this:

  • It can break the ice
  • Often you meet really interesting people
  • It can give everyone a sense of relief that the awkward silence in the elevator is over
  • It can be fun
  • And yes, it can at times be awkward, which is also fun

I challenge you to speak to more people in elevators in your life and see if any unexpected connections arise. Just yesterday through an elevator conversation I connected two complete strangers and likely got one guy a job as a chef!

Thanks Rob for being the ever patient room-mate and friend that you are with all of my bizarre work in creativity and for participating in this video.

Today’s lesson?

Talk To More People.

Day 23 – Teach What You Need To Learn & Listen More

These lessons go hand in hand for me as I’ve learned many things as a teacher and facilitator in my 30s by teaching them to other people. This listening thing is something that I’ve struggled with due to my never ending enthusiasm to share stories and tales of my unique life with anybody who will listen. I know that I’ve made some progress in this area over the past decade but still have work to do.

Everybody can benefit from listening more.

Thank you for that lesson Chelsea. It was very kind of you to point this out to me.

Today’s lessons?

Teach What You Need To Learn & Listen More.

Day 24 – Trust, And Learn When To Say No.

Today I was very fortunate to attend The Habit of Trust workshop that was hosted by Ila Edgar of Big Change Inc.  Throughout the day she took us deeply into discussions about trust.

One of the most noteworthy things that came up for me was when we started talking about “no”. Many people – myself included – are brought up throughout our careers to feel unable to say no to our employers or other people in our lives. But it turns out that there are a number of ways in which you can manage this. You can tactfully say no, negotiate, say yes but ask what needs to be dropped in order to fulfill the new task or ask for further information. This is something that I’ve improved upon in my 30s that has allowed me to have greater control of my life.

Today was a refreshing reminder of the power of NO. Thank you Ila for the excellent facilitation and the meaningful dialog that you created today.

So today’s lesson:

Trust, And Learn When To Say No.

Day 25 – See Family As Friends.

I’ve been very fortunate not just in my 30s but my entire life to have a best friend in my amazing, talented, funny, super-positive twin sister. She and I have always supported each other and as adults have really become great friends.

Of course not all siblings are so lucky. We feel that even when there are tensions, it’s a good idea to think of your family members as friends as that support comes in very handy with the challenges that life brings to us.

Thanks Twin for being my #1 fan and unending supporter.

Today’s lesson?

See Family As Friends.


  • Days 1 – 5 please click HERE.
  • Days 6 – 10 please click HERE.
  • Days 11 – 15 please click HERE.
  • Days 16 – 20 please click HERE.
  • Days 21 – 25 please click HERE.
  • Days 26 – 30 please click HERE.