As I approach 50 in mid-2027, I’ve been thinking a lot more about responsibility, legacy, and mortality. What I’ve realized is that responsible adulting is hard. One misstep and you or your loved ones could be screwed for life.
Ultimately, life is a series of financial quests for survival before we die. If we don’t successfully complete one quest, we end up compounding our failures with new ones. And the brutal truth is that the quests are not independent of each other, they are a chain.
Fail to build a six-month emergency fund, and you raid your 401(k) during a downturn. Raid your 401(k), and you lose a decade of compounding. Lose that compounding, and you can’t save enough for your children’s education. Can’t save for education, and your child starts life with $100,000 in debt. Now their first financial quest is just to get back to zero, the same damn zero you started at.
Miss one quest badly enough, and you don’t just fall behind. You set off a cascade that echoes through your children’s lives and perhaps their children’s lives too.
A Basic Financial Quest: Be Wealthy Enough Not To Burden Your Children
In my post on the shocking cost of eldercare, I realized that my parents succeeded in the financial quest of taking care of themselves. They got long-term care insurance a couple of decades ago, which covers about $10,000 a month for up to three years, inflation adjusted. As a result, they have thoughtfully alleviated much of the burden of eldercare for me and my sister.
That said, after running the numbers on best-in-class eldercare costs, I’ve decided I need to go on a new financial quest of my own: save or make an additional $1 million over the next 10 years. There’s no way I’m letting them go without access to the best care possible if needed. This include me being there to care for them as well.
My parents worked long enough in the U.S. foreign service – 30+ years – to earn lifetime pensions from the government. They paid off their house. They saved and invested in the stock market. As a result, they achieved an important financial quest: being completely self-sufficient. Not having to financially support them in retirement is a privilege my sister and I must never take for granted.
But My In-Laws Need Help
Unfortunately, my mother-in-law has failed her financial quest to be financially independent in retirement. She took out a home equity line of credit that has ballooned. She carries revolving credit card debt and has very little savings. My wife must help manage her finances and her estate, and ultimately we will need to spend a significant amount covering many of her costs.
If I had known about her situation sooner, I could have helped. But she is a private person and I was focused largely on our own finances, and then my parents. My father-in-law lives humbly in a cabin in the woods, just the way he likes it. He is also self-sufficient, but with government support as a veteran.
The basic financial quest of being financially self-sufficient so nobody has to take care of us would solve so many downstream problems. Life is already hard enough trying to build enough wealth for ourselves and our children. Failing this one quest doesn’t just hurt you. It transfers the burden, with interest, to the people you love most.
The Various Quests We Must Undertake Before We Die
Here are the financial quests all of us should undertake. I’ve reordered them slightly in order with the expectation life constantly twists and turns in unexpected ways.
1) Learn the fundamentals of investing before age 12. The sooner you understand risk, reward, and the power of compounding, the better. A child who understands that money grows differently than one who doesn’t. This quest sets the foundation for every other one on this list.
2) Earn enough income to contribute to a Roth IRA as a kid. By working a job, you build grit, social skills, and a real appreciation for hard work and money. A few thousand dollars invested in a Roth IRA at 16 is worth more than most people realize by 60.
3) Have the hard money conversation with your partner before marriage. Financial incompatibility is one of the leading causes of divorce, and divorce is one of the single most financially devastating events that can happen to a person. One avoided conversation early on can cost you half of everything later. This quest is uncomfortable. Do it anyway.
4) Get adequate life insurance before you have dependents. Term life is cheap in your 20s and 30s. The best time to get life insurance is when you’re 30, and the best duration you can get is a 30-year policy. Miss that window and a sudden death leaves your family scrambling to cover a mortgage, childcare, and lost income at once. One missed premium can unravel decades of careful planning overnight.
I used Policygenius to compare term life quotes from multiple insurers in about 10 minutes. It’s free, there’s no pressure, and getting coverage when you’re young and healthy is one of the cheapest financial decisions you’ll ever make. Don’t leave your family exposed to a quest they shouldn’t have to take on alone.
5) Build a 6–month emergency fund before you invest aggressively. Without this buffer, one job loss or medical crisis forces you to liquidate investments at the worst possible time — often at a loss, and with tax consequences that sting for years.
6) Get disability insurance while you’re young and healthy. Most people insure their car and their home but forget to insure their most valuable asset: their income. A serious illness or injury in your 40s, before you’ve hit financial independence, is the quest-ender nobody talks about. The odds are higher than you think. Check with your employer whether they automatically have disability insurance built in.
7) Max out your IRA or 401(k) every year. Paying yourself first forces you to prioritize saving over spending. It is not optional. It is the lever everything else depends on.
8) Negotiate aggressively at every career inflection point. Compensation compounds just like investments do. A $20,000 salary negotiation miss at 30 could cost you $500,000 or more in lifetime earnings, raises, and retirement contributions by 60. Most people leave enormous amounts of money on the table simply because asking feels uncomfortable.
9) Save and invest enough to come up with a 20% down payment on a home. Getting neutral on real estate and fixing most of your living costs is foundational for achieving financial independence. Paying rent indefinitely means your largest monthly expense never stops growing. Establish housing security.
10) Build a taxable brokerage at least equal to your tax-advantaged retirement portfolios. It is your taxable portfolio, not your 401(k), that will generate the passive income and flexibility to live more freely before retirement age. If you want financial freedom in your 40s or 50s, this is where it comes from.
11) Save and invest to the point where your passive income covers your living expenses so you can escape your job. This is the big one. The number most people cite is 25X to 50X your annual expenses. But getting there requires every prior quest to have been completed reasonably well. Skip one, and the finish line moves further away.
If you don’t know exactly where you stand on every financial quest, you’re flying blind. I’ve used Empower’s free financial tools for years to track my net worth, investment fees, and retirement projections all in one place. Another fantastic tool is Boldin, which was build from the ground up with retirement planning in mind. It is an even more comprehensive retirement planning tool.
Financial Quests To Take Care Of Your Children
12) Superfund each child’s 529 plan. College tuition rises faster than inflation every year. Don’t assume your child will get financial aid because they’re talented, or that you’ll qualify because income is modest. Plan as if you’re on your own.
13) Build a custodial investment account during your child’s first 18–23 years of life. Your goal is to teach your children how investing works and provide them with real optionality after graduation. It’s not just a head start, but a financial education they can actually use.
14) Teach your children the difference between assets and liabilities before they turn 18. Building wealth for the next generation is only half the quest. If they don’t understand how money works, they’ll spend an inheritance in years that took you decades to accumulate. This one is on you.
15) Buy one rental property when each child is born. After 18 years, you’ll have a cash-flowing asset that can help pay for college or supplement your retirement. If neither is needed, the asset can provide affordable housing for your child while they get their footing in an expensive world. This is one of the most important goals every real estate investor with children should have.
However, not everyone can or wants to be a landlord. If the idea of buying a rental property when each child is born appeals to you but the reality of tenants, toilets, and maintenance doesn’t, Fundrise is worth exploring. It lets you invest in a diversified portfolio of private real estate starting with as little as $10. I’ve used it as a way to get real estate exposure without the operational headaches of direct ownership.
16) Establish a revocable living trust and ensure your estate is in order. Make sure there is a clear explanation of who gets what, along with a death file containing all usernames, passwords, account numbers, and contacts. The administrative chaos that follows an unorganized estate is a burden you can easily prevent.
Financial Quests For Retirement
17) Understand your Social Security strategy before you claim. Claiming at 62 versus 70 can mean a difference of hundreds of thousands of dollars over a lifetime. Too many people claim early out of fear or ignorance and permanently reduce their income floor in the years they need it most. Based on my research, the best age to take Social Security is 67. It’s the right balance.
18) Review your insurance coverage, estate documents, and beneficiaries every 3–5 years. Life changes always. We have divorces, births, deaths, and windfalls. Outdated documents can send your assets to the wrong people entirely.
An ex-spouse listed as a beneficiary on a 401(k) will legally receive those funds regardless of what your will says. Don’t let an administrative oversight undo a lifetime of work. Put together a death file with all your usernames and passwords and send it to someone you trust.
19) Pay off all debts before you retire. In retirement, simplicity is a form of wealth. Fewer obligations mean fewer things that can go wrong.
20) Save enough to provide for five years of eldercare for yourself. This way, your children or other relatives won’t have to pay for your care. My parents did this. Not everyone does. The ones who don’t often discover, too late, what burden they’ve left behind.
21) Save enough to provide for five years of eldercare for your parents and in-laws if necessary. It is our responsibility to take care of our parents given they cared for us for the first 18–23 years of life. This quest is not always fair. It is rarely convenient. It is still ours to complete.
22) Establish a Donor Advised Fund (DAF) to give more efficiently. If you’re fortunate enough to accumulate more than you need, donating appreciated stock through a DAF is one of the most tax-efficient ways to give. The recipient gets the full value of the donation, while you avoid paying capital gains taxes on the appreciated shares.
The Financial Quests Never Really End
Foolishly, I once wrote about a parent’s existential crisis after all their financial obligations are met. I wondered what happens to purpose once you’ve saved for college, bought rental properties, and built custodial accounts for the kids. The reality I’m finding out is that financial quests never end.
Maybe in 10 years, college will be dramatically more expensive, and a bear market worse than 2008 will wipe out more than half my net worth. Suddenly I’m 60, grinding to recover what I lost, running out of time and energy.
In another 10 years I’ll be 70. Maybe both kids will hit financial rough patches and need help getting back on their feet. And then pretty soon I’ll have no more energy or life left in me, and the responsibility will pass entirely to my spouse and children.
That is the arc of a financial life. It doesn’t end with a trophy. It ends with a handoff.
FIRE didn’t mean fewer quests. It just meant I could see them more clearly, and better choose which ones to take on and when.
Since leaving the traditional workforce in 2012, I’ve watched time accelerate in a way nobody warned me about. The kids were born. The years collapsed. Suddenly I’m writing this and wondering how we got here so fast.
Be careful spending so much energy on the financial quests that you can forget to live the life the quests are supposed to protect.
Enjoy the Wealth You’ve Built
So while you’re moving from one financial quest to the next, don’t forget this one: purposefully enjoy a percentage of your wealth in a carefree, deliberate way.
Part of the reward must be yours, especially if you have excess investment gains.
You stayed disciplined while others may have YOLOed. While managing your own retirement, you planned for your parents’ expenses. You built custodial accounts for your children and negotiated for raises you half-felt guilty asking for. You earned the right to spend some of it – without justification, without guilt, without turning it into another optimization problem.
After all, you were vital in keeping your family’s legacy intact. That is worth celebrating, even if just for a moment, before the next quest begins.
And it always does.
Readers, what are some other financial quests worth mentioning? Have you gotten tired of all the financial quests out there? Is there any wonder why people hire a financial advisor or have trouble getting all of them done?
Free Financial Analysis Offer From Empower
Complete your financial quests with Empower, the web’s #1 free financial app. Track your cash flow, x-ray your investment portfolio for excessive fees and inappropriate risk exposure, and use their retirement calculator to plan for the future.
This is the last month I’ll be mailing out signed copies of Millionaire Milestones for those who take advantage of Empower’s free financial check-up this year. You can read about my experience and the promotion instructions in this post. I’ve taken advantage of three free consultations with Empower over the past decade and each session has helped me better understand my finances.
Financial Samurai is a promoter of the Empower Advisory Group, LLC (“EAG”), and is not currently a client.
