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

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

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Cater Your Goal Planning to What Works for You

Tom’s first piece of advice? Don’t force yourself into someone else’s system.

So many people struggle with goal planning because they try to follow a rigid framework that doesn’t fit their style. Some people need to get directionally right and then just get started.

Other people want to detail everything out so they know exactly where they’re going.

The key is to be directionally right and then go to the level of detail that actually supports you moving forward.

Take Stock of Where You’ve Been and Where You’re At

Tom uses a GPS analogy. Before you can map out where you’re going, you need to know where you’re starting from.

This is where reflection comes in. Look at where you’ve been. What worked? What didn’t? Where are you right now?

As Tom puts it, your results are perfectly designed for who you have been and the actions that you’ve taken. So if you want different results in the future, you have to look at who you need to become and what you need to do differently.

The Wheel of Life: Personal and Business

Tom starts with a framework called the Wheel of Life. It sounds fancy, but it’s simple.

Personal Wheel of Life

First, identify the core pillars that are important in your life. Maybe it’s your marriage, your health, your finances, your faith. Then ask two questions for each area:

On a scale of 1 to 10, where would you rate that today?
What would need to be true to get it to a 10?

This gives you a starting point and shows you the gaps between where you are and where you want to be.

Tom and his wife actually do this exercise separately with about 10 categories, then come together and share their responses. This can be a quick 15-minute activity or a multi-hour deep dive, depending on how detailed you want to get.

Business Wheel

You can do the same thing for your business. Look at:

How much revenue did you make this year?
How much were you able to take home?
How is your time going?
How did your major projects go?
What are your biggest challenges today?

Level set on where you’re at with the business. Now you’ve got a starting point for both personal and business planning.

Close Your Eyes and Imagine Yourself a Year Out

Once you know where you’re at, Tom’s favorite question is this: Close your eyes and imagine you’re at December 31st of next year. What would make this year a 10 out of 10?

Just let it flow. Maybe you lost 10 pounds. Maybe you increased your take-home income by $5,000 a month. List out everything that would make it great.

Then flip it. What would not make it great? What would disappoint you about this year? List those things out too.

This is similar to what Brian Scudamore from 1-800-GOT-JUNK calls his painted picture vision. He projected out five years early in his business and described being at a million dollars in revenue and on the Oprah Winfrey show.

Then he worked backward to figure out what had to happen today to start moving toward those goals.

Be, Do, Have

This is the framework that ties everything together.

Start with what you want to have in the future. Then work backward to figure out who you need to be and what you need to do to get there.

Nathan Barry from ConvertKit is a great example. When ConvertKit was at $30 million ARR, he said to get it to $100 million, he would have to become a different leader and a different CEO. He bought into that personal growth challenge of becoming a higher-level leader.

Mile Markers, Milestones, and Breaking It Down

A year-long goal is great for direction, but you have to break it down into smaller pieces.

Think of them like mile markers on a highway.

Let’s say you want to add an extra $5,000 in income this year. Break that into four mile markers: $1,250 by the end of Q1, $2,500 by the end of Q2, and so on.

Then break it down even further. What does that mean per month? Per week? Per day?

If you don’t understand how you’re progressing day by day or week by week, you’re not going to be able to adjust. And that’s one of the biggest issues most people have with goal planning. They set a goal once at the beginning of the year, maybe give up three weeks in, or think they’re doing the right things, and then get to the end of the year and realize they’re not even close.

Time-Bound: How Long Is Too Long?

Tom’s take: Always have longer-term goals, but the further out they are, the more blurry and less detailed they should be.

When Tom set his goal to retire by 35, he was 21 years old. He had no idea how he was going to make it happen. But he knew the direction.

As he broke it down along the way, he focused first on getting clear on how much money he needed and trying things to make that additional money. Several of those things didn’t work out, but a couple of them did that ultimately got him there.

The key is to have direction and the longer-term goal, but the further out it is, the more likely it’s going to shift. You’re better off focusing on what’s in front of you and getting more detailed there.

Most Goals Are Fake

Paul Jarvis, author of Company of One, dropped this line: Most goals are fake.

He explained that he set a goal to make a million dollars and have a million-dollar business. Three weeks in, he was making himself miserable. And he realized, I don’t need a million dollars. It was a fake goal. It was just an arbitrary number.

Tom’s advice: Ask yourself why you want that goal. Use the Five Whys exercise. Keep asking why until you get to the real reason.

It’s not really the thing we set that we want. It’s the meaning or feeling we associate with it.

When I make a million dollars, then I’ll be worthy.
When I make a million dollars, then I can buy that house.

Then ask: Is that goal necessary or even the best way to achieve what you actually want?

In most cases, we don’t need nearly as much as we think we do. We just have a story in our head that the goal will get us what we want.

The Gap and the Gain

Tom is a big fan of the book The Gap and the Gain. Most people live in the gap. They look at what’s missing and how far they still have to go.

But living in the gain means appreciating how far you’ve already come.

When you set a goal to make $5,000 and you make $4,500, most people say they failed. They look at the $500 they missed and not the $4,500 they made.

That’s why reflection is so important. You’ve got to have something to strive for, but also appreciate what you’ve already achieved. You’re not starting at the very bottom of the mountain.

Simple Questions to Gain Clarity on Your Goals

Tom borrows from Dan Sullivan’s books about scaling simply and 10X is Easier Than 2X.

What Would It Take to Accomplish That in 4 Weeks?

If you give yourself a long timeframe, you have a lot of options for how to achieve a goal. And most times, you’ll stick in other things that aren’t really required.

But if you condense that timeframe, you cut out so many options. Only a couple are left, and those are usually the best ones. Constraint breeds creativity.

So if you have a goal to hit $5,000 in a year, ask yourself: What would it take to hit $5,000 this month? That completely changes how you think about solving the problem.

Speed can be a weapon.

What Would It Look Like If It Were Easy?

This is a Tim Ferriss question. How can you bring a sense of ease and even fun to the process?

Sometimes we can’t make a decision. We’re stuck between two options. Tom’s advice: Ask yourself, What would you need to know to make that decision easy?

Sometimes it’s not about making the decision. Your next action is about getting more information or trying something so the decision becomes easier.

Be Committed, But Not Attached

This is one of Tom’s biggest mindset shifts.

When we try something and it doesn’t work, we tell ourselves a story. It didn’t work. I’m a failure. This is never going to work. All the people who said you shouldn’t start a side hustle were right.

But if you realize that was just one way it didn’t work, and you’re still committed to getting the result, then you show up the next day and just try something different.

Designing Experiments Around Your Goals

Tom treats his attempts like experiments from high school science class.

Start with a hypothesis: I believe if I do this, I’m going to achieve that. Then give yourself a timeframe.

At the end of the experiment, ask: Is this showing progress where I should continue? Or should I pivot or let go and try something else?

Usually in your gut, you’ll figure out if you’ve tried enough things and it’s not gaining momentum. Then it’s time to go back and try something else.

Process Goals vs Outcome Goals

Tom emphasizes the importance of process goals over outcome goals.

For weight loss, the outcome goal is losing 30 pounds. But the process goal is having a 500-calorie deficit every day through working out and watching what you eat.

You can’t control the scale at the end of the week, but you can control the daily deficit. That’s the thing that creates the result.

It’s really important to understand the correlation. A lot of people will say, I need to go make more money, so let me go make all these social media posts. But if we don’t understand how that thing is going to lead to the result, we may do a ton of actions that don’t get us there.

How Can We Test the Hypothesis?

Identify what your hypothesis is. Then say, how can we test it? We might test it for a week, we might test it for a month.

If we can check in, that’s going to help us say, the process things we’re doing are leading to the results, so let’s do more of them. Or the process things aren’t leading to the result, so maybe let’s change that or try something different.

Tracking Dashboard: What Gets Measured Gets Managed

When we think about tracking, there’s the ultimate result. In our case of adding an additional $5,000 in income, that’s the end result.

But what we want to think about is: What are the leading indicators or the things we can track on a daily or weekly basis?

If we’re breaking this down, the goal might be to add an additional $500 this month. We may break that down and say we’re going to add an additional $100 this week.

Whatever that goal is for the week or the day, we want to know what it is. Then every morning, look at where we’re at and adjust our actions based on that.

Sharpen the Saw

A lot of business owners are neck-deep in the weeds, putting out fires day to day. It’s very much maintenance mode versus growth mode.

How do you get people to come up for air when they feel too busy chopping down trees to sharpen the saw?

Tom uses a technique called future pacing. He walks people through two scenarios.

Scenario 1: You’re too busy to do this planning, and you just keep doing what you’re doing today. Then what happens?
Scenario 2: You carve out the time, get super clear on what you want, and create a good plan to get there. Then what would happen?

By the time you get to the end of both scenarios, the question becomes:

Do you want pain now (the planning) to make it easier later? Or do you want it easier now by not doing the planning and the pain later?

Usually that helps people realize it makes sense to do the harder thing now.

Using AI as a Goal-Planning Partner

Tom has been using ChatGPT to level up his goal planning, and the results have been incredible.

His advice: Feed in as much information as you can. The more context you give it, the better the responses are going to be.

Here’s his process:

Have it interview you: Tom created a personal AI in ChatGPT (the $20/month plan) and had it interview him on all the Wheel of Life categories. He spoke his responses into it, and ChatGPT summarized everything for him.
Create a project: Each category became a different folder. He has one for health, one for marriage, one for business.
Get a roadmap: Tom told ChatGPT where he wanted to be a year from now, and it gave him a roadmap. The first version was about 80% of what he would have done, and then he gave feedback to tweak it.
Daily check-ins: Every morning, Tom tells ChatGPT 10 things he’s grateful for. At the end of the day, he gives it his daily rating and summarizes what went well and what his challenges were.

ChatGPT connects everything back to his goals and gives him ongoing feedback and recommendations for where he can adjust. It’s like an accountability partner.

For example, ChatGPT noticed a correlation between Tom’s energy being low and some things he wasn’t doing. It reminded him that when he does those things, his energy is higher, and it recommended he focus on incorporating them back in the next week.

Pro tip: Use the voice feature. You can type 40 to 50 words a minute, but you can talk 150 words a minute. Tom goes on 15-minute walks and just brain dumps what he’s thinking. All of that context helps ChatGPT give better responses.

Tom also mentioned Wispr Flow, a tool that allows you to talk and have it translate into text. He uses this during his goal planning sessions with business owners so they can talk out their responses, then feed them into ChatGPT to get their initial plan.

What’s Next for Tom?

Tom is excited about how AI is going to fundamentally change so many things for business owners.

He’s focused on helping business owners leverage AI properly so they can spend more time in their zone of genius. His goal is simple: help people be happy and live their ideal life.

Tom’s #1 Tip for Side Hustle Nation

“Take time to think about what you really want and be intentional about achieving it.”

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