2026 Financial Planning First Round Draft
Every April, NFL general managers make decisions that define the next decade of their franchise. The best ones are not just finding the best player available. They are finding the right player for the right role. Because the best player available in the wrong position does not just underperform. It puts both the player and the team in a position to fail. Some franchises nail it. Some spend the next decade trying to explain why they did not.
I have been thinking about that a lot lately as it relates to financial planning. Because most people approach their financial lives the same way a bad general manager approaches the draft. They reach for the flashy pick. They take what looks good on paper without thinking about how it fits the rest of the roster. They ignore the unglamorous positions that actually win championships. And then they wonder why the whole thing never quite comes together the way they imagined.
So here is my version of the first round. Ten picks, evaluated by the same four criteria for each: how impactful it is, how immediate the need is, how much it contributes to personal fulfillment, and how significantly it multiplies net worth over time. I will also tell you which ones you can trade up for, which ones you can afford to be patient with, and the one pick that almost every single person takes first overall that I would honestly just punt on.
Every pick gets a position on the field. Because a financial plan is not a product. It is a roster. And rosters only win when every player understands their role and how it fits with everyone else on the team.
Pick 1: Wealth Identity Assessment — Franchise Quarterback
This is the pick nobody makes, and it is the one I am most passionate about. Before we look at a single number, we spend serious time figuring out who you actually are as it relates to money — how you make decisions, what you genuinely fear losing, and what wealth means to you at an identity level. Two people can walk into my office with identical net worths and identical tax situations and need completely different plans, because they are completely different people. The entire offensive system is built around the quarterback. Your financial plan should work the same way.
Most Impactful 10/10
Most Immediate Need 10/10
Personal Fulfillment 10/10
Net Worth Multiplier 9/10
Dive Deeper: Why the Wealth Identity Assessment is the first overall pick →
Pick 2: Tax Planning — Center
The center snaps the ball on every single play and never appears on a highlight reel, which is the perfect metaphor for tax planning. Here is something I tell clients all the time: people tend to let the tax tail wag the planning dog. Taxes are enormously important, but they are only effective when considered as part of a total financial picture. A decision that saves you fifty thousand dollars in taxes this year while quietly costing you three hundred thousand in long-term wealth is not good tax planning. It is tax theater.
Most Impactful 10/10
Most Immediate Need 9/10
Personal Fulfillment 6/10
Net Worth Multiplier 10/10
Dive Deeper: Why most people have a tax preparer but not a tax strategy →
Pick 3: Philanthropic Strategy — Tight End
The tight end blocks like a lineman and catches like a receiver. They do two jobs at once, and most teams never use the position correctly. Philanthropic strategy belongs this high because it is one of the most powerful tax tools available and almost nobody thinks about it that way until it is too late to fully take advantage of it. When it is done correctly, it does not cost you nearly what people assume. In many cases it redirects dollars that were already heading toward a tax bill toward causes you have actually chosen.
Most Impactful 9/10
Most Immediate Need 8/10
Personal Fulfillment 10/10
Net Worth Multiplier 9/10
Dive Deeper: Why philanthropic strategy is a tax pick as much as a legacy pick →
Pick 4: Liquidity and Exit Planning — Left Tackle
The left tackle protects the quarterback's blind side. The hit that ends a season almost always comes from the direction the quarterback cannot see. For business owners, the exit is the single largest financial event of their lives and almost always the one they are least prepared for. Most have seventy to ninety percent of their net worth sitting in a single illiquid asset with no exit structure and no plan for what comes next. I have sat across the table from people in exactly that situation. It is painful to watch and entirely preventable.
Most Impactful 10/10
Most Immediate Need 10/10
Personal Fulfillment 8/10
Net Worth Multiplier 10/10
Dive Deeper: Why business owners are most exposed on their blind side →
Pick 5: Risk Management — Free Safety
The free safety is the last line of defense. You never appreciate how important they are until they are not there. Risk management is consistently undervalued because it is invisible when it is working. Nobody calls their advisor to say thank you for the disability coverage they never had to use. But I have had conversations with families where the presence or absence of the right coverage at the right time meant the difference between financial security and starting completely over.
Most Impactful 9/10
Most Immediate Need 9/10
Personal Fulfillment 5/10
Net Worth Multiplier 8/10
Dive Deeper: The pick nobody appreciates until the moment everything depends on it →
Pick 6: Estate Planning — Fullback
The fullback is a largely forgotten position in the modern game. And then one day you are in a short yardage situation the whole season is riding on and you realize you do not have the player you need. Estate planning is the financial fullback. People know they need it, mean to get around to it, and then life keeps moving until suddenly the situation is urgent and the options that were available five years ago are no longer on the table. Done well it is a tax strategy, a family communication tool, and a legacy document all at once.
Most Impactful 9/10
Most Immediate Need 8/10
Personal Fulfillment 7/10
Net Worth Multiplier 8/10
Dive Deeper: Why estate planning is never urgent until it suddenly is →
Pick 7: Debt Architecture — Running Back
This is the contrarian pick of the draft. Most people have been taught that debt is bad, get out of it as fast as possible, and treat the day your mortgage is paid off as a life achievement. I understand where that instinct comes from and I respect it. But for high-income professionals and business owners, it often quietly costs more than people realize. Debt architecture is the intentional use of debt as a tool, and for the right person at the right time it is one of the most underutilized levers in building long-term wealth.
Most Impactful 8/10
Most Immediate Need 6/10
Personal Fulfillment 5/10
Net Worth Multiplier 9/10
Dive Deeper: Why the most contrarian pick on the board might belong higher →
Pick 8: Investment Management — Wide Receiver
Here is where I will lose some people, and that is fine. Investment management is pick 8. Wide receivers get all the attention, sign the biggest contracts, and appear on every highlight reel. And a great wide receiver on a team with no quarterback, no line, and no scheme is just a very fast, very expensive player going nowhere. Investment management only works as well as the plan it is serving. The financial services industry has spent decades suggesting otherwise. It benefits from that belief.
Most Impactful 9/10
Most Immediate Need 7/10
Personal Fulfillment 7/10
Net Worth Multiplier 9/10
Dive Deeper: Why the most celebrated pick on the board is not pick 1 →
Pick 9: Alternative Investments — Special Teams
Special teams can completely change the field position of a game. Those plays do not happen every drive, but when they do they can swing the entire momentum in a way that conventional offense and defense cannot replicate. Alternative investments work the same way. Private equity, real estate, private credit, structured products — these are not the foundation of a portfolio. They are field position changers. But this is not a pick for someone who does not yet have picks 1 through 8 in place.
Most Impactful 7/10
Most Immediate Need 5/10
Personal Fulfillment 6/10
Net Worth Multiplier 8/10
Dive Deeper: When alternatives change the game and when they just add complexity →
Pick 10: Retirement Planning — Punter
We are going to punt on it.
Not because it is unimportant. Because the way most people use it — as the entire point of the financial plan, the destination everything is aimed at — is the wrong frame, and it quietly causes real harm.
Most people spend the better part of a year planning every detail of their wedding. The venue, the flowers, the dinner, the guest list, all of it. And then the wedding is three hours long, and the next morning there is a strange letdown because it went by so fast and there is nothing left to plan. Retirement planning done the wrong way is exactly that. People spend decades optimizing for an event and arrive there having never decided what the life after the event was supposed to look like.
The wedding is not the marriage. Retirement is not the life.
Build the roster right and you will never need to rely on the punt.
Most Impactful 7/10
Most Immediate Need 5/10
Personal Fulfillment 4/10
Net Worth Multiplier 7/10