Sometimes it's better to be lucky than skilled. Back in February 2009, I was a middle-school writing teacher with a budding interest in stocks. I made my first real investment that month -- the greatest time in modern history to buy stocks.

That said, my journey as a beginning investor was far from perfect. I made plenty of mistakes -- which you'll read about below.

March 2020 is the closest thing we've come to the market upheaval of the Great Recession of 2008-09. If I could travel 11 years back in time, I'd tell myself these five things.

smart phone displaying the words: "the past is calling."

Image source: Getty Images

1. Find your "date" and post it

You must understand why you're investing. For most, the reason is simple: "To save for retirement." As market volatility continues, it's paramount to remember that.

Whatever your reason is, figure out the date -- your "date" -- when you think you'll need to withdraw this money. Write it down and be specific (even though such specificity is silly, it focuses the mind). Then, post the date wherever you are when you check the stock market.

I've chosen my 65th birthday. Here's what my wall looks like right now:

Note that says Sept. 13, 20146

Yes, now you know my birthday and age. In lieu of birthday gifts, please make donations to your local food bank! Image by the author.

Market volatility will make you nervous. If that causes you to think about selling your stocks, look at this date.

2. You won't get rich quick

Next, accept that you won't get rich quick. Right now, there may seem to be a ton of "deals" available, stocks that have fallen 50% or more from their highs.

Here's the thing: there's absolutely no rule that says those stocks can't continue going down -- eventually losing 100% of their value today. The very fact that some stocks have lost so much is a signal from the market that danger lurks.

Investing in March of 2020 is not about getting rich quick. It is about responsibly using money that you know you won't need for at least three years to plant the seeds of long-term wealth creation. 

Just as redwood doesn't sprout overnight, you shouldn't expect your portfolio to do anything miraculous in the days, weeks, or months ahead -- and that's ok.

3. You won't time the bottom

No one wants to buy into a falling market. You want to get your timing just right and maximize your returns. Here's the thing: You'll never do that. And even if you do, you won't know it was "the real bottom" until weeks and months later.

Case in point: On Nov. 20, 2008, just after the election of Barack Obama, it looked like the market had finally bottomed. Over the next seven weeks, the market climbed 24% -- producing remarkable short-term gains.

^SPX Chart

^SPX data by YCharts

Then, reality slapped anyone who thought they'd correctly called the bottom right across the face. Here's what the next seven weeks looked like.

^SPX Chart

^SPX data by YCharts

The cruel twist: Back on March 9, 2009, I actually did buy shares of Alphabet for just $150 apiece. I promptly sold them at $200 because I hadn't followed my first bit of advice: I was focused on the short-term, not the long-term.

4. The real leverage: Find your "enough"

Here's the crazy thing: The real financial leverage you have over your life doesn't come from investing. It all comes down to personal finance. 

I'm not saying investing doesn't help -- it clearly does. But unless you get your own finances in order, you shouldn't be investing a dime anyway. If you want a check-list of "DOs," it would include:

  • Building up an emergency fund to last six months without any income.
  • Paying for all reasonable insurance (life, health, auto, home, disability, renters').
  • Paying off high-interest debt.

But if you want to take a more philosophical approach, you can delve deeper. Find your level of "Enough" -- the amount of physical comforts you absolutely need to feel contentment on the inside. My guess: It will be lower than you think.

5. Become antifragile

Once you find that level, refuse to raise it unless absolutely necessary. Why? Because it will make you "antifragile." If you're unfamiliar, this is a word coined by former trader, risk specialist, and best-selling author Nassim Nicholas Taleb. Something is "antifragile" if, when placed under non-fatal stress, it not only doesn't crumble, but grows stronger.

Being antifragile is counter-intuitive. It calls on you to:

  • Give up efficiency for redundancy: If you're efficient with your money -- putting every last cent in the stock market and keeping none in emergency savings -- you'll have far fewer options and less flexibility when times like these come again, and they will come again.
  • Focus on eliminating downside instead of maximizing upside: Let's go back to insurance. Paying for disability or long-term care insurance can be expensive. And it's painful -- you could be using that money on so many other opportunities. But it limits your downside. That's what one football player discovered after getting injured. Learn from his lesson.
  • Don't rely on your job, get a side hustle: Finally, if you're employed in a standard 9-to-5, remember that your job isn't as secure as it might seem. You have a single employer. If that employer fails or changes its evaluation of you, you'll suffer immediate consequences. The self-employed, who have tens if not hundreds of individual "employers," have far more flexibility.

But here's a secret toward making this all easier: Curiosity and gratitude are by far the most powerful antifragile tools you have at your disposal. They both contribute more to your well-being over time -- regardless of circumstances. Practice them daily, and much of the above will take care of itself.

Hopefully, when the next crisis arrives, you'll know you've taken the steps now to prepare.