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

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Jan 1, 2026

Guest

Tom Sylvester

Join Tom Sylvester, a serial entrepreneur and business coach, as he dives into powerful goal-setting strategies. Tom shares a GPS-style approach to planning, helping listeners define their current state and map out milestones. He emphasizes the importance of breaking big goals into actionable steps and suggests using AI for accountability. Discover how to focus on meaningful goals rather than superficial ones and learn techniques to balance long-term vision with short-term actions—ensuring your year is both productive and fulfilling.

46:45

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Episode notes

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ADVICE

Shrink Timelines To Force Clarity

Condense the timeframe as a thought experiment to simplify choices and reveal the best paths.
Ask, 'What would I change to achieve this in a fraction of the time?' to force creativity.

volunteer_activism

ADVICE

Be Committed, Not Attached

Be committed to the outcome but not emotionally attached to a single method.
When a tactic fails, treat it as data, iterate quickly, and try a different approach.

volunteer_activism

ADVICE

Run Goals As Experiments

Treat goals as experiments with a hypothesis, timeframe, and evaluation criteria.
Run the experiment, check for proof of progress, then decide to persist, pivot, or stop.

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Start With a Wheel of Life Check-In

01:26 • 36sec

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GPS Metaphor: Know Your Starting Point

02:02 • 4min

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Imagine Year-End: Define a 10/10 Year

06:06 • 2min

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Results Reflect Your Actions

07:42 • 3min

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Break Big Goals Into Mile Markers

10:51 • 2min

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Long-Term Vision vs. Short-Term Detail

Focus on Meaning, Not Badge Goals

16:51 • 4min

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Condense Timeframes to Simplify Choices

20:37 • 3min

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Be Committed, Not Attached

23:31 • 1min

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Run Experiments with Clear Hypotheses

24:37 • 1min

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Use AI as a Personal Accountability Partner

25:50 • 5min

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Keep Tech Simple: Tools to Use

Get Stakeholder Buy-In by Asking Their Why

37:46 • 3min

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Plan Now to Avoid Greater Pain Later

40:22 • 2min

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Focus on Zone of Genius and Leverage AI

42:33 • 2min

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Balance Creation with Gratitude Daily

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Company of One

Why Staying Small Is the Next Big Thing for Business

Paul Jarvis

In 'Company of One,' Paul Jarvis challenges the conventional notion that business growth must always mean scaling up. He argues that staying small can provide more freedom, independence, and a better quality of life. The book offers practical advice on setting up a solo business, determining desired revenues, keeping clients happy, and dealing with crises. Jarvis emphasizes the importance of resilience, autonomy, speed, and simplicity in running a successful 'company of one. ' This approach is particularly appealing to solo entrepreneurs and small business owners who prioritize a balanced and fulfilling life over traditional growth models.

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The Gap and The Gain

The High Achievers' Guide to Happiness, Confidence, and Success

Dan Sullivan

Benjamin Hardy

This book introduces the concept of 'The Gap and The Gain', developed by Dan Sullivan, which helps high achievers understand why they are often unhappy despite their accomplishments. It explains that measuring oneself against an ideal (the Gap) leads to dissatisfaction, while measuring against past achievements (the Gain) fosters happiness, gratitude, and motivation. The book is a masterclass on positive psychology, healthy relationships, mental well-being, and high-performance, offering practical advice on how to shift focus to appreciate progress and achieve greater fulfillment and success.

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• Mentioned in 98 episodes

10X Is Easier Than 2X

Dan Sullivan

Benjamin Hardy

The new year is upon us and with it comes a certain level of optimism and maybe even obligation to make some changes, set some meaningful goals, and aim for some big wins.

But it's no secret that most New Year's resolutions fail and a lot of goals lose steam after just a few weeks. To help make sure that doesn't happen to you, I've recruited my good friend and master goal planner Tom Sylvester to join us today.

He's a serial entrepreneur, real estate investor, author of the book Lifestyle Builders, and head business coach at 2x.co. Tom set a goal to retire by 35, later retired young, and now helps six and seven-figure business owners scale up without burning out.

Listen in to Episode 716 of the Side Hustle Show to learn:

how to plan your year without burning out
a GPS-style approach to goal setting
how to turn big goals into daily actions

Full Show Notes: Your Best Year Yet: Goal Setting and Action Planning that Gets Results

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About The Side Hustle Show

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