Have you ever noticed the topic of investing rarely comes up in casual conversation among peers? In this age of emotional intelligence, vulnerability is encouraged when discussing personal feelings, but vulnerability about finances isn’t as normalized. Many parents were not educated on investing themselves and therefore have no knowledge to pass on to their children. In addition, many children do not receive proper education on investing and finances through their school curriculum.

As a result, many people are not well versed in how to financially plan for their future. According to a 2022 Gallup poll, only 58 percent of Americans reported that they own stock. (Of course, differences in net worth, income, higher education, race, and age all play a large role in stock ownership.)

Whether you’re close to retirement age or have been thinking more about your financial preparedness, it can be helpful to take other people’s experiences into account. Here, seventeen people of various ages, careers, and socioeconomic backgrounds share a look into their financial well-being and goals. This is not reflective of a scientifically accurate cross section of the population but rather a more personalized snapshot of how varied your own social network might look across generations.

Disclaimer: These stories are for entertainment purposes only and should not be taken as financial advice. For questions about investing or financial management, reach out to a financial advisor. 


Gen Z  

J, 22, insurance adjuster
I haven’t invested yet, but I want to start. I was not taught how to invest and didn’t have a good role model. I have been talking recently with my older sister’s friend to get on the right path.

Obstacles: I don’t know what to do.

E, 26, freelance model
I started investing when I was twenty-three. My parents taught me the basics of managing money, and my little brother taught me about investing and retirement planning.

My current investment strategy is to annually max out my Roth IRA, keep semiliquid money in a high-interest checking account, and build income history so I can invest in property within the next two years. I’ve already paid off my student loans and other debt. I wish I’d started investing in my Roth IRA sooner.

Obstacles: Trying to figure out what is best for me can be overwhelming with so many options out there.



B, 28, speech language pathologist
I was twenty-six when I started investing. My parents said I should always have a savings to cover at least six months of rent. I also read about the 50-30-20 rule online: 50 percent of your paycheck goes to needs, 30 percent to wants, and 20 percent to savings.

I try to put 20 percent of all my paychecks into my personal savings account, although some months I can only save 10 to 15 percent. I also enrolled in a 403(b) plan provided by my employer.

Obstacles: I am uncertain of what to do, and have a lack of income. I am considering working with a financial advisor but haven’t followed through with that yet.

H, 31, environmental engineer
I was twenty-two when I had some input on investments that were in my name and began my own investments at twenty-six. My parents led by example and were available to give guidance and answer questions when things came up. Having a parent who has done a lot of investing is a baseline leg up in just knowing what exists.

I have an IRA/401(k) and a financial advisor. I put off hiring a financial advisor for a while because I felt like I should be able to do it on my own, but I’m glad I have one now. I acknowledge that I’m privileged, and I don’t have hurdles like student loan debt.

Obstacles: It’s intimidating and involves effort. I also think it’s tough to decide how to balance growing your own wealth with knowing that a lot of financial investing can be problematic on an ethical level.

T, 32, self-employed artist / former software engineer
I was twenty-four when I started investing. Despite my dad working in finance, I did not learn about investment from my parents. Investment came to me very accidentally as tech company stock that slowly vested over my time as a full-time software engineer. I learned the basics from other employees and blog posts.

I was raised to be thrifty, and I was generally nervous of the financial world. I didn’t have a credit card until I was twenty-three and needed a credit score in order to rent an apartment, and since then I’ve treated credit cards as a necessary evil to play the credit game more than as a source of financial freedom. To this end, I’ve had a lot of luck and economic privilege that has allowed me to make safe and conservative financial decisions, which is not an option for everybody.

I bought a house in 2019, which was a pretty good time to do so. This was really a factor of having luck, the means, and a smart and honest real estate agent. Common advice that I’ve heard is that real estate is one of the best investments to make, and as an added bonus, you can live in it.

I have a financial advisor for investments; I’m very hands off.

Obstacles: I don’t have enough interest, and my income is limited at the moment as an artist.

R, 35, software engineer
I was introduced to investing young through high-yield savings accounts and CDs in addition to my normal savings account. I had heard of mutual funds from overhearing chats between my grandfather and my mom and began investing in them at twenty-one. I studied business; some of my favorite classes were finance. I worked at Vanguard right out of college and learned a lot about retirement planning. I started trading crypto and derivatives when I was twenty-seven after chatting with coworkers at an investment company.

I have both Roth and traditional IRAs and Roth and traditional 401(k). I self-manage my long-term mutual fund account. I also have a discretionary derivatives account and would like to have an automated trading account soon. My overall strategy has been to keep expenses low.

Obstacles: I don’t have enough time to build the right tooling.

B, 39, human services / real estate investing 
My first investment was a life insurance policy at age eighteen offered through an employer. My first retirement investment was through an employer at age twenty-two. My first taxable brokerage account was at age thirty-six. My mother was frugal, and I learned some habits from watching her. Neither parent taught me about investing, though. I learned from friends, books, videos, and social media.

I have a Roth IRA—I had a pension, but I wasn’t vested, so it’s a traditional IRA rollover. I also have a 403(b) from my previous employer and date targeted funds.

I wish I had started my Roth IRA sooner and put money into assets that produced higher returns instead of paying off my debt so aggressively. I also wish I would have made more money sooner instead of struggling for so long.

Obstacles: Income is always a factor along with not having access to mentors and feeling like my options are limited.

J, 40, farmer
I learned investing from my parents and grandparents as well as being self-taught. At one period in my life, I was taking a lot of risks. But after I lost some money, my investing has become conservative. I stick to property and stocks with a lot of volume that pay back dividends.

Obstacles: I would say fluid currency inflation, sudden changes in policy, and rising interest rates.

T, 40, computers and management
My mother taught me not to spend money and to put what I haven’t spent somewhere. Family members also tended to give me bonds for my birthday instead of cash.

I paid off high-interest loans around the age of twenty-five. I was twenty-seven when I bought property. I realized I could pay it off twice as fast by doubling the principal, so at the start you get almost a whole month back. I put that money into the low interest rates offered early in the COVID-19 pandemic. At thirty-eight, I began investing in stocks. I also have a Roth and 401(k) and would consider insurance an investment.

Obstacles: If I had more money, I would invest more. Sometimes I’ve felt more conservative than I should be, so I didn’t get enough return. I’ve had ideas that maybe would have made a lot of money, but I never dug into them too much.


Gen X

C, 44, IT project manager
I was nineteen when I began investing. My parents taught me, but I also read books and subscribe to services like Motley Fool and Seeking Alpha. Right now, my strategy is a mix between dividend growth and growth stocks. I wish I wouldn’t have sold the few shares of Amazon I bought twenty-five years ago and then sold after they went up 20 percent.

Obstacles: The main one is time.

G, 45, vendor program manager
I started contributing to a 401(k) at age twenty-four, and I converted my first house into a rental at thirty-nine. My father told me that if you can buy something with someone else’s money, do it, because it leaves the money you have in hand available to make other money.

Obstacles: It sounds contrary to my strategy, but debt payments can block available resources. Balance and especially foresight is necessary to use your available assets in the best way.

V, 45, product manager at a big corporation 
I started investing when I was twenty-six. My parents taught me about saving and investing, and I also taught myself. My strategy is to diversify and have a mix of everything. My advice to others would be to set aside whatever you can each month to invest. Trust the power of compounding interest—don’t touch it for thirty years. And put 80 percent in index funds.

Obstacles: I would say a fear of the unknown and market volatility. 

M, 45, network engineer
I was twenty-three when I started investing. My father was very frugal growing up. His obsession with saving as much as possible had both a positive and negative impact on me.

Initially, I managed a portfolio but switched to using all target date funds after a couple of years. I maxed out my Roth IRA for as long as I was eligible and saved the maximum available in 401(k). My strategy was to max out every tax-deferred benefit there was, keep costs low, and use a passive strategy.

Obstacles: I have less income to invest now that I have a hefty mortgage and two kids.

R, 47, user research
I was twenty-two when I began investing via the 401(k) program at my first job out of college. My parents were not helpful in this area. I’m very lucky that my older cousin taught me to max out my 401(k) no matter what. But I didn’t know anything else until I randomly ended up working at BlackRock at age thirty-four and learned about investing while researching how fund managers and advisors select their investments.

My strategy is ETF based (exchange-traded funds) mixed asset class portfolios using either robo-advisors or a target-date fund (from whatever company is providing my company’s retirement fund), making sure I invest enough to max out the company match and choosing a target date later than my actual target retirement age to get the asset allocation that is a bit more aggressive. I wish I had invested in a rental property earlier.

Obstacles: I’ve noticed a weird mental resistance to spending more time and effort on it.

C, 51, library director / church secretary / dog trainer
My parents taught me how to budget, but no one taught me investing. Where I come from (the Kensington section of Philadelphia), people don’t have money to do that. It’s one of the most impoverished areas in the United States.

I don’t have any investments. I live paycheck to paycheck and still don’t make my monthly bills. This is mostly because of the rare illnesses that I’ve had throughout my life. I put most of my money toward medical bills and medical debt.

Obstacles: I have no money.


Baby Boomers

P, 67, part-time licensed optician
I always saved but didn’t start to invest until my early thirties. I was raised by a Depression-era Jewish mother who could make a dime out of a nickel. I learned from the best about living within my means. As I had no 401(k), my first investment involved $10,000 and a meeting with a financial advisor. My cousin helped me initially, but I’ve been investing on my own for a while now. If I could go back in time, I would start younger and put more money away. I’ve always lived within my means and paid off everything before I retired (though I ended up going back to work part-time).

Obstacles: I never made a lot of money.

L, 75, physician
I was thirty-one when I started investing in CDs and money markets. At age forty, I invested in mutual funds. My parents didn’t educate me on investing and perhaps did the opposite. My dad bought some stock in Rite-Aid, and a few years after that, it lost money. And he never invested in stocks again. I read about investing on my own, whether it was financial columns in the newspaper or articles in magazines. I’d say I would have invested more in the stock market, but it’s easy to say that in hindsight. If I could give advice, I’d tell people to start early. People at every level of financial ability can put a little something aside. And you should do that because it multiplies.

Obstacles: I had a family and had to make sure there was always something there. I had to be somewhat conservative.

Regardless of what generation you fall under, conversations surrounding investing for the future are invaluable. Initiate these talks in your own circle and reach out to a financial advisor to learn more about your options for investing for the future.


Important Disclosures

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investment(s) may be appropriate for you, consult your financial professional prior to investing.

Investing involves risks including possible loss of principal. No investment strategy or risk management technique can guarantee return or eliminate risk in all market environments.

There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.

Asset allocation does not ensure a profit or protect against a loss.

Throughout this communication, the terms “financial advisor” and “advisors” are used to refer to registered representatives and/or investment advisor representatives affiliated with LPL Financial LLC.

This article was prepared by ReminderMedia.

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