I’ve never been good at active investing. My judgment is wrong. (I’ve learned this the expensive way over the years.)

So nowadays, my entire stock investment strategy?

S&P Index fund.

Simple:

I’m not wired for active investing.

Every time I’ve tried to ‘be smart’ and pick a winner, I’ve either lost money or underperformed the S&P 500.

Passive investing works for me in the market.

But – it’s the WORST mindset for managing your career.

In investing, I overestimate opportunity and underestimate risk.

In my career? I’ve often UNDERestimated opportunities and OVERestimated risks.

Looking back on 25+ years in digital marketing, I can’t think of a single time when a BOLD career move – moving cities, changing roles, joining a startup – truly backfired.

If anything, I wish I’d taken MORE risks.

What stopped me? Fear.

I used to apply a PASSIVE strategy to my Business ‘life’. But my career demanded ACTIVE investing.

The truth: When I quit my last ‘safe’ job in 2010 to launch Delve Deeper, it wasn’t because I suddenly became fearless.

I quit because I didn’t want to look back, old and wrinkly … with regret.

Why didn’t I take more BIG BOLD risks when I was younger?

Why did it take being 37 – married, with two daughters, and a mortgage on a New York City home I could barely afford – to finally quit a well-paying marketing job and start my entrepreneurial journey?

Why was I more cautious before I had a family, even though I had much less to lose?

I could have taken much bigger swings back then with almost no risk.

Recently, I bought matching T-shirts for myself and my business partner.

They both read: “Hold On. Let me OVERthink this.”

We wore our T-shirts to the office in December. Yes, my sense of humor is dry, often self-deprecating.

The truth?

We ALL OVERthink. We OVERestimate the risks.

Age doesn’t matter. Fear of change shows up at every stage.

I see younger team members paralyzed by self-doubt instead of burning brightly – or even failing spectacularly in their 20s.

I see old friends narrowing their career options - instead of leaning on decades of their own experience to have the courage to reinvent themselves in their 50s.

My career clarity? It’s come from taking painful risks, forgiving myself for my many mistakes, and always learning from every experience.

Was that easy? Not. At. All.

Every benefit comes with a cost. Having ‘no regrets’ today was paid for with many gut-wrenching decisions and plenty of self doubt.

Want to live with no regrets in your Business ‘life’?

Here’s how I think about it, in four steps:

Step 1: Get Out of Your Comfort Zone.
What scares you most at work? Leading a team? Taking a role that pays more, but also demands more? Changing careers entirely because today you’re just counting the minutes till 5 p.m.?

Step 2: Develop a new skillset.
Do nothing – yet. But first be brutally honest with yourself. What does your intuition say you should do, but your emotions scream discomfort? Clarity starts right there.

Step 3: Create more value – today.
Change is hard. Always. But we don’t have to overhaul our entire life overnight. I remind myself to lean into the process. Just start by asking: What would make my career feel more fulfilling? Greater clarity will lead to action.

Step 4: Set yourself up for bigger roles.
Every major upgrade in my career always started with an idea (such as a restless desire to break from the autopilot.) What bigger role could you capture if you listened more to your intuition?

(Btw, the above 4 steps follow my Return on Marketing Career (RoMC) framework - to learn about RoMC, read this post.)

Why do we get risk so wrong?

Humanity has evolved over many thousands of years with very little in the way of natural defences against predators. So we tend to overvalue the benefits of staying where we are (Safe) compared to those of moving on to pastures new (Risky). There may be more fruit to eat in that valley over there, but how can we be sure it’s not full of bears? Or lions? Or both? Let’s stay in our cozy cave instead.

We’re also wired to value the perceived security of the status quo more highly than the potential for future gains. In Status Quo Bias in Decision Making, Samuelson and Zeckhauser explain how this discourages us from making moves that could lead to greater opportunities.

We’re also biased more towards fear of failure than towards possible success, as Kahneman and Tversky investigate in Prospect Theory.

And here’s the kicker. We think we’re better at predicting outcomes, than we are – particularly negative ones. This often leads to inflated perceptions of risk, as Moore and Healy investigate in The Trouble with Overconfidence.

If you’d like to discuss your career journey with me one-to-one, please feel free to email me at [email protected] or message me on LinkedIn.

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