The Obstacles

Why You Don’t Do What You Should Do When Making Money Decisions

Tyler is 26.

• He makes $54,000 doing IT support in Columbus, listens to three personal finance podcasts at 1.5 speed, and keeps a budget template on his desktop.
• He can explain a Roth IRA at a party. His savings account has held roughly the same $1,900 for two years.

Knowledge arrived years ago. Action is stuck in the driveway.

I have watched this gap for more than 30 years and the pattern holds at every income. Master Your Cash Flow: Let Them Eat Cake and Build Wealth Too! identifies the obstacles to improving financial decisions, and sorts them into two families: practical and emotional.

Naming and dealing with yours is most of the fight.

A 2025 Talker Research survey found that:

• 77% of Gen Z expect to work past the typical retirement age to make ends meet.
• 49% believe they will need to work full-time.
• 29% believe they will need to work at least part-time.

Obstacles are the machinery behind numbers like those, and machinery can be taken apart.

The Four Practical Obstacles

These can be broken into 4 categories:

1. Goals with no dollar figures attached
2. Nothing written
3. No process to follow
4. No roadmap

The first one does the most damage, because most people can describe the life they want and have no idea what it costs.

Here’s an example:

Emma worked as an administrative assistant at a law firm and wanted one thing in the near term: an apartment without roommates.

We asked what she would need to earn to cover the apartment, her loans, her expenses, her taxes, and the parts of life she refused to drop, the vacation, the dinners, the concerts, the daily latte.

She had no idea, so we totaled it together. The number came to about double her current pay, and it flattened her for an afternoon.

When she put that number into action:

• She asked her employer about her earning path and got a straight answer: the ceiling was low.
• She moved to another firm as a legal assistant, closed most of the gap, and covered the rest with part-time admin work for small companies.
• She got the apartment. Within a couple of years, the side work was optional, so she kept only the pieces she enjoyed, and the last time we spoke she was mapping a run at a chief operating officer role.

Notice the shape of that story. Emma’s obstacle dissolved under arithmetic, and her climb ran through employers that would help solve the goal the whole way.

Be An Apple

Companies face the same four obstacles and treat clearing them as routine. Apple knows the profit it is aiming for this year, the earnings per share, the return on equity, and other financial benchmarks, in absolute numbers and percentages.

I spent years at Merck, and even our corporate tax department ran on budgets we reviewed monthly and quarterly. Well-run companies course-correct during the year. “I wonder how last year went” is a question they never have to ask.

Run your plan the way they run theirs:

• Goals in dollars.
• Written down.
• process for each one.
• A roadmap you check during the year, on purpose, before December.

The Emotional Obstacles

These can be broken into 4 categories:

1. Fear of repeating an old loss.
2. Embarrassment about what you believe you should already know by now, which keeps smart people from asking basic questions for decades.
3. Distrust, earned from a bad adviser or a relative.
4. The cost reflex that influencers farm: pay nothing, just listen, you can do it all yourself. Advice priced at zero tends to be worth the invoice.

Fear and other emotional obstacles respond to recognition and handling it. Your first speech in front of a class terrified you, and you gave it. You dealt with it. Parents describe holding their first child the same way. The fear or distrust may stay. You deal with it. Dealing with it is learnable, and handling is all a financial plan requires.

Seesaw Thinking, And Oliver

The emotional obstacle I see most in people under 30 is what I call the seesaw thinking.

You know what a seesaw is, right? You see them in kid’s playgrounds: one kid sits on one end of a long board, and the other kid sits on the other side of the board. One goes up while the other comes down and visa-versa.

How does this apply to people when making financial choices? Fun now, or savings now. The trip, or the goal. The family, or the career.

Oliver, a 25 year old entrepreneur and a mentee of mine, called one day to tell me that any relationships were off the table until his financial goals were met.

Marriage/partner, kids, house, all of it parked for the decade, if necessary. We talked through a different frame: how about aiming for both? Build the plan so both sides of the seesaw rise.

He reworked his numbers so a personal life fit inside the ambition. Four years later he has a loving partner, a real source of joy in his life, and he has met every financial guidepost he set over those years.

Both sides can rise, and the rest of this chapter is the how.

Real Wealth, And The Gym Story

The book’s reframe is called real wealth. Wealth operates as a portfolio:

• Energy
• Skills
• Relationships
• Experiences
• Reputation
• Money

The assets interact, so improving one usually makes the others easier. Money works as fuel for the rest.

Some spending is an investment: the gym, a course, therapy, flights to see the people you love, when it matches your values and strengthens future choices. For example, a gym membership, run properly, is a plan to prevent future medical bills and feeling great now.

Run properly is the operative phrase. Two people buy the same gym membership:

• Person A buys it, feels guilty, pays with whatever card, doesn’t use it, forgets about it, and carries a monthly charge.
• Person B treats it as an asset: sets a schedule, tracks usage, pays with a card that rewards the category, and clears the statement every month.

Opposite outcomes from an identical purchase. The gap was designed, decision by decision, before discipline ever got a vote.

Tyler ran his climbing gym through this framework. $85 a month with a low hum of guilt every time the charge posted.

The framework said keep it because:

• It provides a real life return in stress reduction and health improvement
• Money returned from the the annual plan saved Tyler money overall
• ($850 for the year compared to $1,020 month-to-month equalled $170 saved)
• The payment returned from his 2% credit card, worth another $17, with autopay clearing the statement so interest never hit.

The purchase stayed. The guilt got cut instead.

You Don’t Have To Give Up Living To Have A Life

Any planner can make you financially independent fast. The recipe: skip the kids, skip the house, live in a shack, eat instant ramen every day. You will hit the number, and you and your significant other may stop speaking somewhere around year five.

A real plan has to hold a real life, and real lives include weddings, kids, illnesses, layoffs, and years that go sideways.

This is the philosophy underneath everything we teach: living the life you want well along the way is part of the plan’s design, and reframing choices and finding cash flow is how both sides of the seesaw rise. The book’s tools exist so the fun survives the math.

Amin’s “Real Wealth” Exercise

Before you spend, ask two questions:

1. Does this purchase increase my options for financial freedom later?
2. Options can look like higher earnings, better health, stronger relationships, less stress, more confidence, or fewer future problems.
3. Can I fund it without interest or chaos?
4. Debt stress can turn an investment into a trade.

Write The Script Beforehand

Motivation can be unreliable, so the book borrows a tool from behavioral research: if-then plans, written in advance, which reliably increase follow through.

The power sits in removing decision making from your weakest moments, tired, hungry, bored, stressed, one click from confirm purchase. One example from the book’s list: if friends suggest an expensive plan, then see if there is a cheaper option first. Choose while you’re calm.

Back To Tyler

Tyler’s version of progress took an evening.

• He named his two loudest obstacles, no dollar figures on his goals and the seesaw in his head.
• He priced the life he wanted, kept the climbing gym on the stack’s terms, and wrote two if-thens, one for checkout and one for payday. The $1,900 finally has somewhere to go.

Obstacles keep their power by staying vague. Named, they turn into a checklist, and a checklist is a very beatable opponent.

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