The Advice I Needed (But Never Got)

When I look back at the winding path of my career, one truth stands out with painful clarity: I wish someone had grabbed me by the shoulders early on and said, "Take more risks."

It's almost comical now to reflect on opportunities I considered "too risky" at the time. The startup I declined to join that later went public (3COM pre-IPO). The unconventional career pivot (Wall Street) I contemplated but abandoned for the safer path.

Human nature steers us toward risk management. We're wired to avoid danger, to seek certainty, to cling to the known. This instinct served our ancestors well when predators lurked behind every tree. But in the modern professional landscape, this same instinct sabotages our potential.

What I've learned through painful experience is that what feels like high risk rarely is. Most professional "risks" aren't life-threatening—they're simply uncomfortable. They demand that we step beyond the boundaries of our self-imposed limitations and familiar routines.

The truth is, playing it safe comes with its own significant risk—the risk of regret. The risk of looking back years later and wondering, "What if?"

Being too conservative in my decision-making created an invisible ceiling on my potential. It's only now, with hindsight's perfect vision, that I recognize how many of my "responsible" choices were actually fear masquerading as prudence.

Had I known then what I understand now, I would have:

• Viewed career "risks" more as experiments than permanent decisions
• Recognized that most professional failures are temporary setbacks, not catastrophes
• Understood that skills are transferable across contexts in ways I couldn't imagine
• Realized that stability often means settling for predictable mediocrity over potential excellence

The most successful people I know aren't necessarily the most talented or educated—they're the ones who consistently took intelligent risks when others hesitated. They understood that calculated boldness, not cautious restraint, is the true path to extraordinary outcomes.

So if you're early in your career reading this, consider it the advice I wish I'd received: the biggest risk is not taking any. Your comfort zone might feel safe, but it's also where possibilities go to die. The regret of inaction ultimately stings far more than the disappointment of failure.

What "risky" opportunity are you considering right now??

Perhaps the real question isn't whether you can afford to take that chance, but whether you can afford not to.

The Risk Reality Framework: 4 Questions to Overcome Decision Paralysis

When facing a decision you perceive as "risky," run it through these four questions:

1. What's the true worst-case scenario?

Not the vague fear, but the specific, realistic worst outcome. Write it down in detail. Is it truly catastrophic or merely uncomfortable? Would you survive it? Most "worst cases" are recoverable situations, not life-altering disasters.

2. What's the opportunity cost of inaction?

Calculate what you're giving up by not taking this risk. Consider both tangible outcomes (potential earnings, skills gained) and intangible ones (personal growth, future regret). Remember that not deciding is itself a decision—with its own consequences.

3. Can this risk be structured as an experiment?

Frame the decision as a time-bound experiment rather than a permanent choice. Could you try this new direction for six months? Can you create a small test case before fully committing? Breaking big risks into smaller experiments reduces the stakes while still moving you forward.

4. What would I advise someone I care about in this situation?

We're often wiser when advising others than when making our own decisions. Imagine a friend or loved one facing this exact choice—what would you tell them? This perspective shift often cuts through our own emotional barriers.

This post originally appeared on my Substack “Phil McKinney’s Studio Notes”. This is where I post first and then share later to a few others social media platforms. You can sign-up for a free subscription.