Podcast Summary: The Side Hustle Show

Episode 716: Your Best Year Yet – Goal Setting and Action Planning that Gets Results

Host: Nick Loper
Guest: Tom Sylvester, serial entrepreneur, real estate investor, author of “Lifestyle Builders,” head business coach at 2x.co
Release Date: January 1, 2026

Overview

In this actionable New Year’s episode, Nick Loper is joined by Tom Sylvester to break down the most effective ways to set, plan, and actually achieve meaningful business and personal goals in 2026. Tom, a master planner and entrepreneur, shares practical frameworks, mindset shifts, and innovative tech (especially AI-powered tools) to help you move from vague resolutions to intentional progress. He also covers making goal-setting collaborative (with your spouse or team), staying motivated, and how to know when to quit a path that isn’t working.

Key Discussion Points & Insights

1. Why Most Goals Fail & Where to Start

Nick’s confession: He hasn’t done New Year’s resolutions or long-term goal planning for years, often struggling with picking a “North Star” (00:48).
Tom’s approach:

• Acknowledge everyone’s struggle with goal planning and stress the importance of making the process personal and adaptable (01:25).
• Start by assessing where you are right now, both personally and in business.
  • Use the Wheel of Life exercise: Identify key life areas (e.g., health, relationships, finances, faith, community).
  • For each: “On a scale of 1 to 10, where am I today?” and “What would need to be true to make this a 10?” (03:00)

Quote:

“If we don’t know where we’re at now, it’s going to be so hard to figure out where we want to go.” – Tom (03:56)

2. Visioning the Ideal Future

• Use future projection: Imagine yourself on December 31, 2026 (or a year ahead).
  • Ask: What would make this year a 10 out of 10? What would be disappointing? (06:06)
• Compare to notable frameworks from other guests, like Brian Scudamore’s “Painted Picture Vision.”

Quote:

“Your results are perfectly designed for who you have been and the actions that you’ve taken.” – Tom (07:42)

• Tie in “Be-Do-Have” principle: Define what you want, who you need to become, and then the actions to get there (09:23).

3. Breaking Goals into Actionable Steps

• Start with the long-term target, then work backward.
  • Map out yearly, quarterly, monthly, weekly, and daily “mile markers” (11:09).
  • Example: If you want to add $5,000 in income, break it into manageable increments across the year, down to weekly/daily actions.

Quote:

“Having a 5k goal by the end of the year is good. But if we don’t understand day by day or week by week how we’re progressing, we’re not going to be able to adjust.” – Tom (11:53)

• Emphasize the importance of leading indicators and input/process goals (i.e., controllable daily actions) vs. just outcome goals (33:52).

4. Ensuring Your Goals Are Real

• Discuss how arbitrary goals (like “a million dollars in revenue”) can be fake or meaningless unless they are deeply connected to your values and actual needs (13:49).

Quote:

“We should be asking ourselves, why do I want that? Because it’s not really the thing that we set that we want. It’s the meaning or the feeling that we associate with that.” – Tom (17:43)

• Use the “Five Whys” method to drill down to the true motivation behind a goal and check if there’s a simpler path to what you desire (17:55).

5. Questions & Frameworks to Drive Action

• Key prompts:
  • “What would need to be true to make this a 10?”
  • “If I had to do this in a fraction of the time, what would I change?” (“10x is easier than 2x” concept) (20:44).
  • “What would you need to know to make this decision easy?” (22:34)
  • “What would it look like if it were easy (or fun)?” (23:06)

6. Mindsets for Resilience

• Be committed, but not attached:
  • If a path isn’t yielding results, learn and pivot instead of giving up (23:38).
  • Use experiments – set a hypothesis, a timeframe, collect evidence, and decide whether to persist or pivot (24:44).

7. Leveraging AI for Goal Planning

• Tom has ChatGPT interview him on life/work categories, summarize his responses, and help map a plan.
• Uses chat-based AI as a roadmap generator and daily accountability partner:
  • Feeds in daily gratitude lists and reflections.
  • Gets weekly feedback and suggested adjustments, e.g., noticing correlations between energy and daily habits (25:58–29:23).
• Recommends using detailed voice notes for greater depth and context (30:06).
  • Mentions tools like Whisper Flow for translating speech to text (31:11).

Quote:

“The more context you give it, the better the responses are going to be.” – Tom (29:36)

8. Tracking & Measuring Progress

• Break outcome goals into weekly/daily process goals (e.g., X sales calls/week, 500 words/day), and regularly review progress (32:54, 33:18).
• Use process goals when outcome data is limited—experiment, measure, iterate (35:37).

9. Getting Buy-In from Spouses/Teams

• Framework for partner/team alignment:
  • Ask stakeholders the same planning questions: Where are you today? Where do you want to be a year from now? What’s important to you? (38:12)
  • Discuss differences in vision/timeline, and jointly agree on priorities (38:58).

10. Making Time for Planning

• Overcome “too busy to plan” by future-pacing two scenarios:
  • What happens if you stay in maintenance mode?
  • What happens if you take time to plan intentionally?
  • Recognizing the long-term cost of reactive living motivates intentional planning (41:15).

11. Balancing Growth with Gratitude

• Keep growth and gratitude in tension:
  • Tom keeps a “create your future” vision board and a “love your life” gratitude wall in his office (44:29).
  • Celebrate the gain, not just dwell on the gap (19:11, 44:29).

Quote:

“We often overestimate what we can do in a year, but we underestimate what we can do in a decade.” – Tony Robbins (as quoted by Tom, 46:07)

Notable Quotes & Moments

• On tailored planning:
  “For some people, we just need to directionally be right, get started and we’ll go from there. For other people, they really want to go in and detail it out more…” – Tom (01:25)

• On consistency:
  “Just realize you’re on the path and you get to go through this process to get there and you can probably do so much more than you think is possible.” – Tom (46:07)

• On AI as a personal GPS:
  “Just like GPS will tell you, ‘Hey, you missed a turn, go back this way.’ ChatGPT is kind of doing that for me with my plan.” – Tom (29:23)

Timestamps for Key Segments

• [01:25] — Where to start with goal setting
• [03:00] — Wheel of Life exercise explained
• [06:06] — Visioning your “10 out of 10” year
• [07:42] — The “results are designed by your actions” mental model
• [09:23] — “Be-Do-Have” principle
• [11:09] — Breaking annual goals into milestones and daily actions
• [13:49] — Are most goals fake? Ensuring your goals are real
• [17:43] — Digging into “why” behind your goal
• [20:44] — Frameworks for action: condense the timeline
• [22:34] — “What would you need to know to make this decision easy?”
• [23:38] — “Be committed, but not attached”
• [24:44] — When to quit: experiment and review
• [25:58–29:23] — Using ChatGPT and AI for custom goal planning & accountability
• [31:11] — AI tools: Voice to text and reflection
• [32:54, 33:18] — Measuring what matters: leading vs. lagging indicators
• [35:37] — Process goals, experimentation, and feedback
• [38:12] — Getting partner/team buy-in: collaborative goal planning
• [41:15] — Future-pacing exercise for prioritizing planning
• [44:29] — Growth, gratitude, and grounding your ambition
• [46:07] — Closing tip: Over/underestimating your power over time

Actionable Takeaways

• Assess your starting point—personally and professionally—with the Wheel of Life.
• Project your future: Clearly define what a truly successful year looks and feels like.
• Drill down: Break big goals into manageable milestones and day-to-day process goals.
• Ask why: Regularly interrogate your motives for each target.
• Leverage tech: Experiment with AI as both roadmap generator and accountability partner.
• Track and reflect: Measure your leading indicators every week; compare the gain as well as the gap.
• Make it collaborative: Pull in your spouse, partner, or team for buy-in and alignment.
• Embrace growth + gratitude: Acknowledge both where you want to go and how far you’ve already come.
• Experiment and iterate: Treat new efforts as experiments—review, adapt, pivot as needed.
• Be intentional: Carve out time to plan—the investment pays exponential dividends.

Resources Mentioned

• Book: Lifestyle Builders by Tom & Ariana Sylvester
• Book: Gap and the Gain; 10x is Easier Than 2x by Dan Sullivan
• Guest mentions: Brian Scudamore, Nathan Barry, Tim Ferriss, Paul Jarvis
• AI tools: ChatGPT (OpenAI $20/mo plan), WhisperFlow
• Free resource: sidehustlenation.com/goals for goal planning template

Final Word

Tom’s #1 Tip:

“Take time to really think about what you want and be intentional with everything you do to get there. You’re on the path, and you can probably do so much more than you think is possible.” (46:07)

Nick’s closing reminder:

“The best way to predict the future is to create it. So, it’s on you to make it happen this year.” (45:32)

For more templates, resources, and actionable tips, download Nick’s goal planning toolkit at sidehustlenation.com/goals