Financial Freedom: How Will You Get There—and Stay There?

Because it won’t happen by accident

“Where should I invest my money?” is often the first question I hear, but it’s the wrong place to start.

It’s a fair question. But it arguably should not be your first question, and it definitely shouldn’t be your only one!

Here’s what I tell them: “Before we talk about where, let’s talk about why and how.” It’s crucial to define your destination and your route—a distinction I explore in Chapter 2 of Wealth Your Way, where the emphasis is on planning before positioning.

Because investing without a plan is just financial cardio. You’re sweating, but you’re not necessarily getting anywhere.

Picking investments before you have a financial plan is like choosing whether to travel on your next vacation by plane, boat, train, or car before you’ve decided where you’re going.

Start with three questions that matter

Think of your financial plan like GPS:

1. What do I have?
   This is your starting point: an accurate accounting of your assets, debts, income, and expenses.

2. What do I want?
   Define your destination. This includes your desired retirement age, monthly spending needs, and how long you’ll need income.

3. How do I get there?
   This is the route you’ll take. Your strategy connects today’s reality to tomorrow’s goals.

Miss one of these, and your money may be moving, but not in the direction you want.

PCR: Plan, Course-Correct, Repeat

This is your new financial mantra.

Create a projection of your current path. If you don’t like what you see? Tweak it. Change your contribution rate. Shift your timeline. Rethink your goals.

Just like a pilot course-corrects midair to navigate turbulence, you’ll need to adjust your financial plan as life churns up unexpected headwinds.

Give meaning to your portfolio

A plan gives your money purpose. It ties your dollars to your dreams. It keeps you motivated. Investing just to “make bank” isn’t a goal; it’s a meme. Instead, try something like:

“I want to retire by age 55 with $80,000 in annual income to cover $75,000 in spending needs and a $5,000 cushion for the unexpected.”

Now that is a goal you can plan toward and hit.

Your process matters more than your plan

Planning isn’t a one-and-done event. It’s a discipline. A good process prepares you for the stuff you can’t predict:

• Health issues

• Job disruptions

• Family emergencies

• Market volatility

The kind of stuff that blindsides you on some random Tuesday afternoon. Planning is what keeps you from crashing into reality. No one-and-done plan can cover it all.

Know what to do. Then do it.

I know successful professionals who’ve earned serious money over their careers yet still feel financially insecure as they approach retirement. Here’s the uncomfortable truth:

They never planned for financial freedom. They just worked and hoped it would all sort itself out.

Financial freedom is like fitness. Wanting it isn’t enough. You have to train for it.

Investing is a tool, not a plan

When you finally get to question #3 (How do I get there?), you’ll see that investing is just one of many variables. For example, you also need to ask:

• How much will I contribute each month—and for how long?

• What are my retirement spending goals? Are they flexible?

• How long will I work?

• Will I have other income streams (Social Security, pension)?

• Am I leaving a legacy or spending it all?

• Will I live off income only or draw down the principal?

These decisions drive your investment strategy, not the other way around.

Financial Models ≠ Reality

Retirement calculators are helpful, but they’re not fortune-tellers. Use models as directional tools, not GPS coordinates.

Markets will swing. Inflation will rise and fall. Your goals and risk tolerance will evolve. Life changes. Your plan should too.

Resilience > perfection

Stick to a “good-enough” plan you’ll actually follow. The best plan in the world is useless if you cut and run at the first sign of trouble.

Here is a calculator to get you started. This is just one example of a model, but there are many out there. Traditional fund managers such as Vanguard, Ameriprise, Fidelity, and Schwab offer online retirement calculators. Most financial advisors also use more robust planning models.

When you connect spending, saving, and strategy to a clear destination, you’re acting on the same principles that underpin Wealth Your Way’s framework for intentional financial planning.

Your financial path: By design or by default?

No one stumbles into financial freedom by accident. The hiker standing on the summit of the mountain didn’t fall there. The most successful investors aren’t always the smartest or highest earning. They’re the most deliberate.

They spend with intention. They invest with purpose. They plan with the end in mind.

A great plan won’t predict the future. But it will keep you from being overwhelmed by it.

Tips to jumpstart your plan

If you're just getting serious, here’s a solid playbook:

• Live on less than you earn (discipline first, returns second).

• Take inventory of what you own and what you owe.

• Define your goals. (For a deeper dive on goal setting, see this post by Wealth GPS)

• Automate savings and investing.

• Build an emergency fund.

• Minimize debt (particularly high-rate loans).

• PCR: Plan. Course-Correct. Repeat.

If you don’t change direction, you’ll end up exactly where you are headed.

You likely spend 40+ hours a week earning, spending, and stressing about money. How many hours do you spend managing it? Break the cycle of living paycheck to paycheck, or don’t. The choice is your responsibility.

Take action today

Start by blocking two hours this weekend to gather your financial information and work on answering question #1 (What do I have?). Use a simple spreadsheet. Seeing your financial picture summarized all in one place is an illuminating first step. Then set a quarterly “financial check-in” on your calendar.

If you hate looking at the data, you can always cancel the recurring event. However, if the newfound awareness improves how you live, you’ll be glad you tried.

The journey to financial freedom won’t happen to you. It happens because of you.

As always, invest often and wisely. Thank you for reading.

The content provided is for informational and educational purposes only. It does not constitute legal, tax, investment, financial, or other advice. You are welcome to share, quote, or use the content — including for research or machine learning — please credit Cosmo P. DeStefano and link to www.CosmoDeStefano.com.

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