Your First Investment: Simpler Than You Think
"I finally opened a brokerage account," she wrote. "Now what? I'm staring at all these options and I feel completely paralyzed. I don't want to mess this up."
I knew that feeling. Not from investing—I've been doing this for almost three decades—but from yoga. The first time I walked into a Mysore room after a year or so of taking twice a week led “power yoga” classes. Now suddenly I was surrounded by people who seemed to know exactly what they were doing while I still was trying to remember what came next in primary series. Everyone else appeared fluent in a language I hadn't learned yet. And the teacher never even came over to say, “hello,” much less to help me. I didn’t go back and it wasn’t until a couple of years later when I met Nancy Gilgoff and Christine Hoar and asked them where to practice in NYC that I got up the nerve to try a Mysore class again.
Here's what I wish someone had told me then, and what I told her: You don't need to learn the whole language to start speaking.
The Myth of Readiness
There's this idea that you need to understand markets, read the Wall Street Journal daily, analyze company earnings reports, and have opinions about Federal Reserve policy before you can invest your first dollar.
You don't.
In fact, trying to learn all of that before you begin is like trying to master anatomy, Sanskrit, and the complete Ashtanga primary series before you ever step on a mat. It's a form of procrastination dressed up as preparation.
The truth is simpler: the best time to start investing was ten years ago. The second-best time is today. And you can start with almost no knowledge beyond this—compound growth works best when it has time.
What You Actually Need
Let me strip this down to what matters for someone taking their first step:
You need:
A brokerage account (Vanguard, Fidelity, or Schwab—all reputable, all have low-fee options)
Some money to invest (could be $50, could be $5,000—the amount matters less than starting)
One investment to begin with
You don't need:
To pick individual stocks
To understand economic theory
To time the market
To have a lot of money
To know what you're doing
That last one always surprises people. But it's true.
The One Investment I Recommend to Almost Everyone Starting Out
Target date funds.
I know that sounds boring. It probably sounds like something your HR department mentioned once during benefits enrollment and you zoned out. But stay with me, because this might be the most useful financial advice you'll ever receive.
Here's how they work:
You pick a fund based on roughly when you think you'll retire. If you're 35 now and imagine retiring around 65, that's 30 years away—so you'd choose a fund dated around 2055. If you're 50 and thinking about retiring at 70, you'd look at a 2045 fund.
That's it. That's the only decision you make.
The fund does everything else.
What the Fund Actually Does
Inside that target date fund is a pre-built, diversified portfolio of index funds. It holds:
U.S. stocks (large companies, small companies, everything in between)
International stocks (because the U.S. isn't the whole world)
Bonds (which provide stability when stocks get volatile)
The mix is age-appropriate. When you're young with decades until retirement, the fund holds mostly stocks because you have time to ride out the inevitable ups and downs. As you get closer to retirement, the fund automatically shifts toward more bonds and fewer stocks. You don't have to remember to do this. You don't have to decide when it's time to "get more conservative." The fund does it for you.
This is called a "glide path," and it's based on research about how risk tolerance should change as you age.
Why This Works
Broad diversification: You own thousands of companies across the entire global economy. If one sector struggles, you're not devastated. If tech booms, you benefit. If healthcare thrives, you benefit. You're not trying to guess which horse will win—you're betting on the whole race.
Low cost: Target date funds built with index funds typically charge very low fees—often 0.10% to 0.15% annually.
Rebalancing: When stocks do really well, they become a bigger portion of your portfolio. That's good, except now you're more exposed to risk than you intended. The fund automatically sells some winners and buys some of whatever lagged, keeping your mix where it should be. Again, you don't have to do anything.
Set it and forget it: You can add money monthly, quarterly, annually—whatever works for you. The fund takes care of allocating it appropriately.
The Yoga Parallel
In Ashtanga yoga, there's something called the Mysore style of practice. You learn the poses one at a time, in sequence. You don't learn the whole series before you start. You learn one pose, you practice it, and when you're ready, your teacher gives you the next one.
This is that first pose.
You don't need to master options trading or read quarterly earnings reports or have opinions about emerging markets. You need to start. To show up. To put some money in motion and let time do the heavy work.
Later—maybe years later—if you want to learn more, you can. You can add individual stocks if that interests you. You can explore real estate investment trusts or sector funds or international small-cap value. But you don't need any of that to begin.
How to Actually Do This
Open a brokerage account. Go to Vanguard, Fidelity, or Schwab's website. It takes about 15 minutes. You'll need your Social Security number, bank account info, and a few basic details.
Transfer money. Link your bank account and transfer whatever you're comfortable starting with. This could be $100. It could be $1,000. It could be the maximum for a Roth IRA ($7,000 in 2025 if you're under 50). Any of these is fine.
Search for a target date fund.
At Vanguard: Search "Target Retirement [year]" - example: "Target Retirement 2055"
At Fidelity: Search "Freedom Index [year]" - example: "Freedom Index 2055"
At Schwab: Search "Target Index [year]" - example: "Target Index 2055"
Buy the fund. Click "Buy" or "Trade," enter the dollar amount you want to invest, and confirm. That's it.
Set up automatic investments if you want. Most platforms let you set up recurring transfers—$50 every month, $200 every paycheck, whatever works. This is optional, but it's powerful. It means you're consistently investing without having to think about it.
What Will Happen Next
Nothing dramatic.
The value of your investment will go up some days and down others. Some years it will grow 15% or 20%. Some years it will drop 10% or more. This is normal. This is not a sign you did something wrong. This is just what markets do.
Your job is to keep adding to it when you can and leave it alone otherwise.
Remember that $1,000 I invested in the S&P 500 in 1997? It's worth almost $13,000 now, even though it went through four major bear markets along the way. The growth didn't happen because I was smart or lucky or timed anything perfectly. It happened because I left it invested and let compound growth do its work.
The Question You're Probably Asking
"But what if I start right before a market crash?"
This is the question everyone asks. And it's the wrong question, but I understand why it feels urgent.
Here's the truth: You might. You might invest your first $1,000 and watch it drop to $800 a few months later. That would feel terrible.
But if you're investing for 20 or 30 years, that early drop won't matter. In fact, it might help you—because you'll be buying more shares at lower prices with your future contributions. This is called dollar-cost averaging, and it's one of the few free lunches in investing.
The real risk isn't starting at the "wrong time." The real risk is waiting so long that you miss years of compound growth because you were trying to find the "right time."
There is no right time. There's only now.
What This Isn't
This isn't a get-rich-quick strategy. Target date funds won't double your money in a year. They won't make you feel like a genius at cocktail parties. They won't give you exciting stories about the stock you bought at $5 that went to $500.
What they will do is quietly, steadily grow your wealth over decades. They'll give you broad exposure to the global economy. They'll keep your costs low and your risk appropriate for your age. They'll let you sleep at night.
This is the financial equivalent of a consistent daily practice. It's not flashy. It works.
One More Thing
After you do this—after you open the account, pick the fund, invest that first chunk of money—you're going to feel a little anticlimactic. You might think, "That's it? That's all there is to it?"
Yes. That's it.
Investing doesn't have to be complicated. In fact, for most people, it shouldn't be.
The hard part isn't the mechanics. The hard part is starting. The hard part is trusting that something this simple could actually work. The hard part is staying invested when markets drop and everyone around you is panicking.
But you already know how to do hard things. You've shown up to your mat when you didn't feel like it. You've held uncomfortable poses until they became familiar. You've practiced patience in the face of frustration.
This is the same skill set. Just applied differently.
Your Next Step
Open the account this week. Not when you feel ready. Not when you've read three more books. This week.
Pick a target date fund close to your expected retirement year. Invest whatever amount feels right to start—even if it's small.
Then come back here and tell me you did it. Or ask me questions. Or tell me what scared you about it. I'll answer anonymously if you want. You can use the question box in my Stories, or there's a form on my website where you can ask anything completely anonymously.
Money conversations are vulnerable. Admitting you don't know something feels risky. But I promise you, most people don't know this stuff. They're just better at pretending they do.
You don't have to pretend. You just have to start.
Want to learn more about investing basics? This is part of my Foundations series, where I'm breaking down essential investing concepts through the lens of yoga philosophy. Next up: why diversification is like a balanced practice, and how putting all your eggs in one basket is like trying to perfect just one pose while ignoring everything else.
Have questions? Ask me anything—anonymously if you prefer. I'll answer the most common questions in next week's post.
Any opinions are those of Berkshire Wealth Group and not necessarily those of Raymond James. Expressions of opinion are as of this date and are subject to change without notice. Every investor's situation is unique and you should consider your investment goals, risk tolerance and time horizon before making any investment. Investing involves risk and you may incur a profit or loss regardless of strategy selected. The forgoing is not a recommendation to buy or sell any individual security or any combination of securities. Be sure to contact a qualified professional regarding your particular situation before making any investment or withdrawal decision.
