If I Could Start My Investing Journey Over Again, These Are the 10 Things I Would Change

I'm celebrating my 50th birthday this year. That milestone makes for a good time to reflect on my wealth journey and share some investing lessons learned.

Maturity and experience with more than one major market crash provide perspective I didn't have a younger investor. While I am reaching my financial goals today, I'd be more successful if I'd been calmer and more disciplined in years past.

Here's a look at my top investing regrets. Hopefully you can use these insights to reach your financial goals faster and with less stress.

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I didn't start investing for retirement in earnest until my late 30s. I had some great excuses, though. I was self-employed, my budget was tight, and I was too busy raising my kids to dedicate energy to my own financial planning.

In hindsight, those excuses all arose from one truth: I didn't prioritize my retirement as a financial goal.

When I reflect on the wealth generated in my kids' college funds -- just from socking away cash gifts from relatives -- I regret not saving even small sums for retirement in my 20s.

The math speaks for itself. Based on the doubling rule, funds invested to return 6% or 7% on average annually will double every 10 or 12 years. By delaying retirement investing until my late 30s, I missed out on an entire doubling cycle.

ALSO READ: Why You Should Save for Retirement When You're Young and Broke

When online trading first became a thing, I approached investing like a game that I could win. That worked out well when the market was hot, and not so well when the dot-com bubble burst.

After the fact, it was clear I'd been overconfident. I didn't know enough about the companies I owned. I bought tech stocks mostly because everyone was buying tech stocks. What's interesting is that I consider myself levelheaded most of the time. Even so, I got caught up in the excitement of a hot market and acted on a fear of missing out.

Today, I see more opportunity in the contrarian approach. If everyone's buying, I consider selling. If everyone's selling, I consider buying. I don't always act on those considerations, but this perspective fends off emotional, overconfident decision-making.

As a younger person, I had moments of feeling like I couldn't afford to save or invest. I've since come to realize that investing any amount, even $5, is a valuable exercise. That's true now more than ever since many brokers offer commission-free trades.

Instead of skipping deposits to my brokerage account when times were tough, I should have established a baseline, nonnegotiable amount to invest monthly -- a dollar-cost averaging approach. After all, even small investments will double and triple over time. Had I saved and invested consistently earlier in life, I would be much richer today.

ALSO READ: How Dollar-Cost Averaging Works in Turbulent Markets

I went through a phase of investing mostly in a taxable brokerage account while ignoring my SEP IRA. My rationale was that I wanted more flexibility than the IRA provided. Even so, I didn't have a clear goal in mind, other than building wealth as quickly as possible.

I've since realized two things. One, investing without a goal or defined timeline is hard. You have no parameters to guide your decision-making. You don't know what to expect other than positive returns -- which isn't always realistic. You're more likely to get distracted and trade too much.

And two, it's a mistake to overlook retirement as a top financial goal. Practically everyone can benefit from investing for retirement. If you don't know why you're investing, do it for your retirement.

The bursting of the dot-com bubble was the first time I watched my own balance drop dramatically. I didn't have much in those days, and to lose a bunch of it felt horrible. I sold most of my stocks at a loss and temporarily swore off investing.

The next big downturn was the 2008 financial crisis. This time, I took the opposite approach, à la Seinfeld's George Costanza. Instead of panicking when the market went into free fall, I invested all my extra cash in an S&P 500 index fund. I did sell off a couple positions that were higher risk. And then, I mostly ignored my portfolio for a while.

It took six years or so, but being calm in the crisis eventually paid off.

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Investing is only one part of our financial lives. Other parts include your spending habits, your debt balance, your cash balance, and the reliability of your income. It's smart to consider the risks in these other areas when formulating your investment approach.

As an example, launching a business with my husband involved a high degree of risk. Our income was sparse and inconsistent. I did not need to be speculating on stocks in those days -- our new business was enough speculation for one household.

The opposite can happen also. When our household income is reliable and debt levels are low, I feel more comfortable taking a more aggressive investing approach.

ALSO READ: Should You Pay Off Debt, or Should You Save and Invest?

I had an epiphany several years ago: I'm a lazy investor. I don't want to approach investing as a second job, where I'm constantly monitoring and searching for new opportunities. I want the freedom to disconnect occasionally from my investments and the financial headlines.

Had I come to this conclusion earlier in life, my investing history would have been much simpler. I would have traded less and kept a more consistent portfolio. I would have bought index funds and blue chip stocks ages ago and kept them for the long haul.

Sure, the buy-and-hold approach isn't terribly exciting, but I am reaching my wealth goals. And I'm doing it without living and breathing the stock market, which is how I like it.

While I've been self-employed for most of my career, I have served time in the corporate world, with access to a 401(k). I contributed to my workplace retirement account, but I could have done more.

I have this perspective now, partly because I manually schedule monthly deposits to my SEP IRA. It only takes minutes, but I miss the automation of the 401(k). I never forgot to make a 401(k) contribution. And those automated annual contribution rate increases in the 401(k)? I hardly noticed them. In hindsight, investing in a 401(k) was so easy, I don't know why I didn't do more of it.

ALSO READ: How Much Should You Contribute to Your 401(k)?

As a younger person, I didn't respect the importance of having emergency cash savings. For noninvestors, cash is good for paying unexpected expenses or bridging a gap between jobs. For investors, cash is liquidity insurance.

You need that liquidity if an unexpected expense happens as the market's going sour. Without cash on hand, you may reach into your portfolio, liquidating assets when prices are down. Selling in a down market often isn't ideal -- especially if you're selling good assets that you'll rebuy later at a higher cost.

Being diversified has financial and emotional benefits. Monetarily speaking, having diversity in your portfolio often shaves off the extremes of normal market volatility. Emotionally speaking, it's easier to stay calm through volatility when some of your positions are holding their ground.

A diversification obstacle you may face today is like the one I faced in the late 1990s -- tech stocks are dominant. Back then, the high-profile tech stocks were mostly start-ups. Today, technology companies dominate the S&P 500. These companies are heavily represented in funds, which may mean you're overexposed without knowing it.

Fortunately, it's easier today to diversify on a budget than it used to be. If you need to branch out but money is tight, try investing in niche funds or fractional shares.

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If I charted my net worth on a graph over time, it would not be a straight line. Like the stock market, my net worth has grown through the decades -- but not without turbulence.

No amount of study or expertise can eliminate those peaks and valleys for an investor. What you can do, though, is soften the volatility by investing consistently, keeping your cool when times are tough, and staying diversified.

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