The Surprising Skill You Need If You Want to Maximize Your Money

Eric Roberge
6 min readAug 17, 2020

This article was originally written for and published on Beyond Your Hammock

The other day, my wife, Kali, mentioned she wanted to thank me for something.

We recently bought a home we both love in upstate New York. It sits on a little mountain and has an incredible, western-facing view.

We were sitting on the deck watching a gorgeous sunset (an activity we don’t imagine tiring of anytime soon), when she said this, and added that it was a bit of a long story to explain.

She said that earlier that day, she was looking out the bedroom window and had a flashback to a time we went to a summer barbecue at a house on Cape Cod.

The host of the party owned a successful corporate education company, and bought the beachfront house earlier that year.

I’m not sure if it’s because the barbecue was one of the first parties they’d thrown at the new place or if he was just the kind of guy that liked to have other people admire his possessions, but throughout the day he’d take various groups around for a full-property tour.

Each tour lasted at least 20 minutes as he covered every last detail of every single designer, high-end appliance, flooring choice, and fixture throughout the house.

Tour groups even trouped down to the basement to check out some kind of fancy plumbing work and hear an explanation of what made it so remarkable (which neither my wife and I remember in the slightest).

Kali looked bemused the whole time and said the only thing she could think of to describe it all was “ostentatious.” It was obvious that the house itself cost a fortune and even more apparent that the work the new owners did in it probably cost as much as the property itself.

Later that day as we drove home from the party, I made a comment about how amazing the whole place was. Kali wrinkled her nose, made a comment about “ostentatious,” again, and then added, “I hated it.”

I couldn’t believe it. Sure, maybe the decor wasn’t completely our style, but to me, it would be such a dream to have a gorgeous, spacious, classic Cape Cod house right on the beach (with a roof deck, to boot!).

It was like something out of a magazine; who could hate that?

Kali explained that, as we had been standing in the master bedroom of the house and looking out at this incredible view of the beach and the ocean, the only thing she was thinking was not, “wow, this is amazing!”…

…but “wow, I will never be able to have something like this.”

Are (False) Assumptions Holding Up Your Efforts to Maximize Your Money?

Kali recounted all of this to me as we sat on the deck at our new house.

“And that’s why I have to thank you,” she said. “Because you literally had the vision to see that something like this,” — she gestured out at the gorgeous mountain view in front of us — “was actually possible and attainable. I didn’t.”

She went on to explain that had it just been her, she would have never even thought to ask “what if?” questions like, “what if we did this or pursued that?”

And without the question, there’s no financial planning work to be done to see if it’s possible. Without allowing yourself to fully explore and own what you want to do, you’ll never know what you can do.

That’s one big secret to getting more value from your financial planning efforts and ensuring you give yourself the opportunity to maximize your money: as cheesy as it sounds, you have to be willing to dream big.

You have to explore the possibilities and see what works and what doesn’t before you assume you already know.

Kali said she would have just assumed that she couldn’t do certain things, because in her mind, she was still that struggling kid out of college whose first “real” job paid her $12 and covered her health insurance and that felt like high rolling at the time.

Mentally, she defaulted to where she started her adult life, with her biggest financial goal being “ability to go to the grocery store and buy whatever I want without having to count every penny of what I put in my cart to make sure I don’t go over budget.”

It didn’t matter that she wasn’t actually that person anymore. She struggled to bring her mind up to speed with how things were now instead of what they were like then.

Between her buy-whatever-I-want-at-the-grocery-store dream and the time she turned 28, she had started her own successful freelancing career and then her own business — which in her most lucrative year, earned her over six times what she made in her first year out of college.

And it didn’t matter that in the last few years, she started working for my firm at Beyond Your Hammock and together we were growing the business and hitting big financial goals like saving 40% of our gross income.

She still assumed that there was so much that she couldn’t do or couldn’t afford. Before even asking the question of, “what if I can?” she had dismissed big ideas as unrealistic and unattainable.

Developing a Vision Is a Skill (and You Can Learn It)

From my work with high-achieving professionals in our Financially Sound program, I know this is not something that’s unique to Kali.

This is a big challenge for a lot of people who are self-made and working to build their wealth from scratch. You may have the ability and the resources, but that opportunity might go to waste if you literally can’t see the path to maximize your money.

You need a variety of tools to make this happen — high incomes, equity compensation, career advancement opportunities, successful businesses, and more — but again, without the ability to envision what you truly want, you may miss out.

If you assume you can’t maximize your money in whatever way that means to you, you’re absolutely right. You can’t do whatever it is that you decided was out of your reach.

You can’t go after something if you don’t even know it’s there for you to pursue. You can’t achieve really big things with your financial life if you don’t even realize that option is available to you.

Of course, dreaming up massive goals and big plans isn’t always easy.

Kali is a prime example of that; even after working in a financial planning firm and spending years as a freelance financial writer, it’s still hard for her to get around her own money scripts, biases, and financial fears.

That’s because the process of goal-setting is a skill you learn, not something everyone can just wake up and do. Choosing abundance over scarcity and acting from a pace of possibility rather than a place of fear are not strategies that come naturally to everyone.

You might have a talent for creating big visions, and if so, you’re ahead of the curve; now all you need to do is partner with a professional who can help you develop an action plan to make that vision possible in reality.

For Best Results, Allow Yourself to See and Explore Possibilities

But you might not know exactly what you want, let alone how to get there… and that’s okay, too. A good planning process should account for that.

My financial planning work never starts with me telling my clients what they want. The process begins with throwing logic and restraints out the window, and simply asking, “what is it you’d like to have or enjoy or do in your life — even if it sounds crazy, impossible, or out of reach?”

We brainstorm from there, with the point being to open ourselves up to what’s possible rather than staying limited with what currently seems realistic.

Yes, financial reality — meaning, what the numbers look like in your situation — has to come back into play before we can build an action plan. But if you let those numbers, or even your perception of what those numbers mean, get in the way before you develop your vision?

You might stop yourself from reaching your full potential. That potential is there whether you believe in it or not. Part of my job is to eliminate thoughts like, “I’ll never be able to have this,” and transform that into a question:

What if I admitted what I wanted? What if I could get there if I was willing to plan for it?”

It’s amazing what opens up when you simply allow possibilities to actually exist.

Want more financial advice you can actually use? Check out Beyond Your Hammock, a fee-only financial planning firm that specializes in helping 30- and 40-somethings get clarity and start building wealth.

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Eric Roberge

#FinancialPlanner helping 30 & 40-somethings build #wealth & think differently about #money • Top #FinancialAdvisor in #Boston • www.BeyondYourHammock.com