The Personal Finance Podcast

Episode: Why You Keep Failing at Money Goals (And the Simple System That Fixes It)

Host: Andrew Giancola
Date: January 5, 2026

Episode Overview

Andrew Giancola shares a comprehensive, step-by-step system for not only setting but also actually achieving your financial goals in 2026. Drawing on his personal journey from living paycheck to paycheck to becoming a millionaire, Andrew identifies common pitfalls in goal-setting, advocates for a systems-over-habits approach, and provides actionable techniques that listeners can implement immediately. The episode is peppered with practical advice, relatable stories, and memorable one-liners, aiming to empower listeners to take control of their financial future for good.

Key Discussion Points & Insights

1. Why Most People Fail at Money Goals (06:45)

• The Pattern of Goal Failure:
  Many set ambitious financial goals at the start of the year, but motivation wanes and goals are forgotten by December.
• Relatable Struggles:
  Examples include trying to max retirement accounts, build emergency funds, buy property, or just get a grip on spending.
• Andrew’s Foundational Philosophy:

  “Habits are for suckers and systems are for winners. Systems are what help you achieve your financial goals.” — Andrew (12:03)

2. The Power of Systems Over Habits (12:00)

• Habits are important, but systems (repeatable processes and tracking methods) are what actually consistently drive results.
• Andrew tells the story of hitting financial rock bottom at a gas station—to underscore the transformational power of drawing a “line in the sand” and committing to change.

3. Step 1: Get Crystal Clear on Your Goals (19:45)

Clarity is Key:

• Set aside time to deeply consider where you want to be—not just this year, but in 2, 5, and 10 years.
• Write it all down—if you manage money with a partner, merge your “why”s.

Guiding Questions:

• What is my why?
• What does success look like for me?
• What are my 5-year, 3-year, and 1-year goals? (31:00)

“If you don’t have a reason why you’re setting up these goals, then you’re never going to stick to it whatsoever.” — Andrew (24:30)

4. Step 2: Set Specific (SMART) Goals (32:40)

• Use the SMART framework:
  Specific, Measurable, Achievable, Relevant, Time-bound
• “We set up SMART goals a bit differently,” Andrew shares, tailoring the framework to real financial life.
• Practical advice: Don’t make goals too big—stretch goals should be just 10% tougher than what’s easily doable.

“A goal without a plan is just a wish. Hope is the wrong thing to ever have when it comes to goal setting.” — Andrew (43:20)

Notable Example

• If you want to save $1,000 in a month, specify how you’ll do it. List tactics (selling items, Uber, etc.).
• For time-boundedness, Andrew recommends the 12-Week Year method—focus on goals in 12-week “sprints” rather than a full year, which keeps urgency and motivation high.

5. Step 3: Break Down Goals into Actionable Steps (46:00)

• Large goals are broken down into smaller chunks: yearly, monthly, weekly, and even daily tasks.
• Andrew uses a “read 52 books a year” analogy to show how breaking into daily page goals makes big results seem manageable.
• Same principle for financial goals (e.g., saving $3,000 in 3 months = $250/week).

“Success is literally that simple. If you just stick to your plan, if you just set up the steps that you needed to do every single day and take those daily actions, you can absolutely accomplish your goal.” — Andrew (48:44)

6. Step 4: Keep Score and Track Progress (59:00)

• “You can’t win the game if you don’t know the score.”
• Develop a scorecard:
  • Define what you’re tracking (savings rate, debt payoff, investment, etc.)
  • Set check-in intervals. Andrew reviews his every Sunday.
  • Make it visual—spreadsheets, charts, even a “red thermometer” progress bar.
• Frequent review (preferably weekly) allows for timely adjustments.
• Tracking should become a habit; build it into your routine.

“My scorecard isn’t a dusty document. I’m looking at this every single week—sometimes multiple times a week.” — Andrew (1:04:18)

7. Step 5: Weekly Planning & Time-Blocking (1:12:00)

• Plan your week in advance, ideally every Sunday.
• Use time-blocking (Andrew uses Google Calendar) to allocate time for priorities—both personal and financial.
• Avoid time “holes”, as they get filled by non-priority tasks.
• Include flexibility and buffers in your plan. Don’t forget personal growth and self-care tasks (reading, exercise, learning).

“Not having my time blocked out every single week is exhausting... If you have a plan in place, you know what you’re doing every hour, every minute of every day, and all of the sudden, you actually feel energized.” — Andrew (1:14:52)

8. Handling Setbacks and Building Consistency (1:21:30)

• “Never miss twice”: If you lapse on a habit or goal one day, don’t let it be two in a row (via James Clear’s Atomic Habits).
• Embrace a “reset, not restart” mentality—don’t throw away prior progress with every slip-up.
• Key to financial goals: Automate your money! Direct deposit, automated savings/investing—remove decision fatigue.

Notable Quotes & Memorable Moments

• On taking control:

  “You can draw a line in the sand today and say, listen, I am going to be the person that changes my family tree.” (11:50)

• On specificity:

  “If your goals aren’t specific, then we have no idea what success is.” (33:05)

• On flexibility and real life:

  “We’re never going to have a perfect goal, we’re never going to have a perfect month. Instead, we just need to roll with the punches.” (1:21:45)

Action Steps Recommended by Andrew (1:32:50)

1. Reserve your spot in the Master Your Money Goals workshop.
2. Schedule a 30-minute clarity session—define your goals for the year.
3. Write down 1-3 key goals for the first quarter, using his system.
4. Implement one financial automation (savings, investing, bill payment, etc.).
5. Plan your upcoming week using the time-blocking ritual.

Recommended Tools & Further Resources

• Goal & Time-Blocking Sheets: Available via the upcoming workshop.
• Automation Checklist: Free, linked in podcast show notes.
• Books Mentioned:
  • The 12-Week Year (for quarterly goal setting)
  • Atomic Habits by James Clear

Timestamps for Key Segments

• [06:45] — Why people fail with money goals
• [12:03] — Systems vs. habits
• [19:45] — Getting clear on your goals and "the why"
• [31:00] — Defining five, three, and one-year goals
• [32:40] — SMART goals explained and customized
• [43:20] — A goal without a plan is just a wish
• [46:00] — Breaking big goals down into daily action
• [59:00] — Tracking progress and using scorecards
• [1:12:00] — Weekly planning and time-blocking
• [1:21:30] — Coping with setbacks and resetting
• [1:32:50] — Andrew’s final action steps

This episode empowers listeners with a battle-tested system for setting and achieving financial and personal goals—starting with clarity, building a system, tracking progress, and making adjustments as needed. Andrew’s approachable style, combined with his detailed breakdowns, makes this a must-listen (or read!) for anyone seeking a breakthrough with their money and personal growth in 2026.