Planting, Growing, Harvesting: Where Does Your Financial Garden Stand Today?
🕐 Read Time 6 Minutes
Key Takeaways
Stop beating yourself up for not hitting that "perfect" financial target and start harvesting the wins you've already achieved.
You wouldn’t run your business without regular financial reviews, so treat your personal wealth with the same intentional oversight.
Even 1% annual increases in retirement contributions can grow into a bountiful financial harvest over time, proving that perfection isn't required for wealth building.
If you’ve ever planted a garden, you know that results don’t happen overnight. You water, you weed, you wait. Then, surprise! Those little sprouts you forgot about suddenly bloom into a whole tomato plant (hopefully before the squirrels get to it).
Money works the same way. The seeds you’ve been planting — retirement contributions, debt payoff, savings habits — don’t grow instantly. They grow quietly in the background while you’re busy running your business, raising kids, or just trying to get through another tax season.
Most of us rarely pause to check in on the harvest. We just keep planting, hustling, and hoping things work out. But what if you actually took a beat to see how far you’ve come? What if you measured your financial growth not by some impossible ideal, but by the progress you’ve already made?
That’s where today’s check-in comes in.
Measuring Backwards to See the Gain
Before we explore the details of financial tracking, let's address the mindset. Dan Sullivan and Benjamin Hardy hit the nail on the head in their book "The Gap and the Gain" when they explain why most of us feel perpetually behind on our goals.
We're constantly measuring ourselves against some idealized future version (the gap) instead of acknowledging how far we've actually come (the gain).
Here’s where The Gap and the Gain mindset make all the difference.
If you only look at the Gap: “Ugh, I should have $1.5M by now, and I’m only at $700K. I’ll never catch up.”
If you look at the Gain: “Three years ago, I only had $350K saved. I’ve doubled it since then. That’s progress worth celebrating.”
This concept is pure gold when applied to your finances. Instead of beating yourself up because you haven't hit that magical seven-figure net worth yet, what if you celebrated the fact that your retirement account has grown by $50,000 since last year? Or that you've finally built that emergency fund you kept promising yourself you'd create?
The gain approach doesn't mean settling for mediocrity or abandoning ambitious goals. It means giving yourself credit for the progress you've made while staying motivated for what's ahead because you've probably accomplished more than you realize.
Money Goal Tracking: Your Financial GPS
Money goal tracking is like a GPS for your finances. You wouldn't start a road trip without knowing where you are now and where you're headed, right? Yet so many successful business owners are financially driving blind, hoping they'll somehow arrive at their destination.
Here's what a proper financial check-in looks like:
Start with your retirement accounts. When did you last actually examine growth, contribution limits, and tax advantages beyond just glancing at the balance?
Audit your savings goals. Remember that house down payment fund you started? The business expansion account? That "someday we'll take a real vacation" savings? Time to assess whether these goals remain relevant and if your contributions are aligning with your ambitions.
Review your investment strategy. Does your portfolio still match your current age and risk tolerance?
Examine your business financials. As a business owner, your personal and business financial health are intertwined. Are you paying yourself consistently? Building business reserves? Planning for tax obligations?
The goal isn't perfection; it's awareness. You can't course-correct if you don't know where you stand.
Financial Future Planning: Beyond the Magic Number
Let's address the elephant in the room: that retirement number everyone obsesses over. You know, the one that's supposed to magically solve all your future financial worries? While having a target is important, financial future planning is far more nuanced than hitting a single number.
Your lifestyle evolves. The retirement you envision at 35 might look completely different at 55. Maybe you thought you'd want to travel the world, but now you're dreaming of a quiet cottage where you can finally read all those books.
Inflation is real. That $2 million nest egg might seem substantial now, but what will it buy in 20 years? Financial future planning means accounting for the fact that today's purchasing power won't match tomorrow's.
Healthcare costs are unpredictable. This isn't meant to scare you, but ignoring potential long-term care expenses is like planning a camping trip and hoping it won't rain. Hope for the best, plan for reality.
Your business is an asset. Many entrepreneurs forget that their business itself represents value. Whether you plan to sell, pass it down, or let it provide ongoing passive income, factor this into your financial future planning.
The key is building flexibility into your plan. Life rarely unfolds exactly as expected, and your financial strategy should be robust enough to handle plot twists.
Retirement Savings Goals: The Entrepreneur's Dilemma
Traditional retirement advice assumes you'll work for 40 years at a steady job with predictable income and employer-sponsored benefits. If you're rolling your eyes right now, you're not alone. Entrepreneurial income is about as predictable as the weather, and traditional retirement planning advice often falls short.
Here's how to approach retirement savings goals when your income looks like a roller coaster:
Automate when times are good. During high-income months or years, consider automatically increasing your retirement contributions. This takes advantage of your earning peaks without requiring constant decision-making.
Consider a Roth conversion strategy. If you have lower-income years (it happens to the best of us), these might be perfect opportunities for Roth conversions, paying taxes now when your rate is lower.
Don't ignore the SEP-IRA. If you’re a business owner, you have access to retirement vehicles that most employees can only dream about. A SEP-IRA allows contributions up to 25% of your income or $70,000 (whichever is less) for 2025. That's serious wealth-building potential.
Plan for variable retirement. Maybe you'll semi-retire at 55 and fully retire at 70. Or perhaps you'll work part-time indefinitely. Your retirement savings goals should reflect your unique vision, not some one-size-fits-all approach.
Remember the business sale factor. Many entrepreneurs plan to partially fund their retirement by selling their business. While this can be lucrative, it's also risky to put all your eggs in one basket. Diversification remains important.
Course Corrections: It's Never Too Late
Maybe your financial check-in revealed some uncomfortable truths, or perhaps you discovered you're doing better than expected but could optimize further. Either way, you're not stuck with the status quo.
Small course corrections now can have massive impacts over time thanks to compound growth. Behind on retirement? Increase contributions by just 1% annually. Ahead of schedule? Explore tax-loss harvesting or estate planning.
The beauty of measuring now and regularly from here on out is that you have options. Your challenge isn't a lack of resources; it's making sure those resources are working as hard as you are.
Your Financial Harvest Awaits
If you’re not sure whether your financial garden is on track — or if you want a partner to help you figure out what to plant next — this is the perfect time for a discovery call.
At Financial Fitness Coaching, we help small business owners, entrepreneurs, couples and individuals align their money with their values in a way that feels good. No restrictive budgets. No one-size-fits-all advice. Just a clear-eyed look at where you are, what you’ve already achieved, and how to get where you want to go.
Book your discovery call today, and let’s start celebrating the gains while planning for the future. Because you reap what you sow, let’s make sure your harvest is worth celebrating.
Frequently Asked Questions (FAQs)
Q: How often should I be checking in on my financial progress?
A: At minimum, do a comprehensive review quarterly, but check your retirement and savings accounts monthly. Think of it like checking your garden — you don’t need to dig up the roots daily, but regular watering and weeding keep things healthy.
Q: What if my financial check-in reveals I’m way behind on my goals?
A: Focus on small, consistent changes rather than dramatic overhauls that you won’t stick to. Increasing retirement contributions by even 1-2% or automating an extra $500/month to savings can create significant momentum over time.