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Start2026Now Party with Chris Cherian, Annie P. Ruggles & Keith Spiro

Ready to Start2026Now? In 2020, when we could not get rid of the year fast enough, I began hosting an annual GoalChat that celebrates starting the new year in DEBcember. This gives everyone a month to simultaneously wrap up the previous year, while ramping up for the next one.

For the last four years, I have been joined by my friends Chris Cherian, Math @ MoMA; Annie P. Ruggles, founder of the Non-Sleazy Sales Academy; and business strategist and community builder Keith Spiro. Keith has been at all 6 of these GoalChats. It’s fun and meaningful to check in, support, and cheer each other on.

This week, we started with a conversation on identity … and in what ways each one of ours has changed/evolved over the past year. Chris, Annie, and Keith also shared their wins and challenges from 2025, along with their goals for the end of this year and for 2026. Happy DEBcember!

2025 Challenges

  • Annie: Patience in the pauses
  • Chris: Readjusting to life outside of corporate; not everything in his personal life is fast paced
  • Keith: Figuring out the messaging for his reclaimed identity; going beyond being known as just a photographer or sales specialist

2025 Wins

  • Keith: Finished the electronic transition to Keith Spiro, Business Strategist; he just launched Maine’s First Ship Inaugural Maritime Concert Book for sale to help grow the awareness of and fanbase for Maine’s First Ship
  • Chris: Got to officiate a wedding – childhood best friend; will keep the consistent writing going
  • Annie: Did her first musicals in 11 years: Gypsy and Once Upon a Mattress, and enjoyed writing/having a musical theatre bio; Plan is to get a business win by the end of the year

2026 Professional and Personal Goals

  • Annie’s Goal: A complete book proposal; complete double mastectomy next year (which she has been putting off)
  • Chris’ Goal: Level-up career; play basketball again
  • Keith’s Goal: Work with the word “discovery” and help people be comfortable with uncertainty; take a long distance train trip

Start2026Now #GoalChatLive

Gifted Goals 

  • Keith: Change one word! Instead of saying or writing “but” use “Yes, and” instead and watch what happens!
  • Chris: Be curious. Allow yourself to be bad at something
  • Annie: Practice self-forgiveness

Final Thoughts

  • Keith: Say “Yes!” If you curious about things, you will be successful
  • Chris: You can “yes, and” your own identity
  • Annie: If you get stuck, remember there are people having a worse time then you. Actively help them!

Links

What are your wins for 2025? Your 2026 goals? Please share in the comments.

Next Week

We are talking about AI with Annika Jackson, Stan Robinson, and Jason Van Orden. Join us on Monday, December 8, at 4pm PT, for #GoalChatLive.

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For more inspiration, motivation, and tips, follow @TheDEBMethod on YouTube, Facebook, and Instagram. And connect on LinkedIn.

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