The Journey: #46 Too Little, Too Late

Lately, I’ve been thinking about timing, not the “trust the universe” kind, but the real-world timing inside startups and scaleups that determines whether you move forward or stall out.

After 13 years in SaaS, I’ve seen a consistent pattern:

Companies rarely suffer because they make the wrong move.

They suffer because they make the right move far too late.

You see this everywhere:

Waiting to hire

Waiting to fire

Waiting to buy the technology

Waiting to invest in onboarding, enablement, CS, or operations

Waiting for the “right time,” which was actually last quarter

The space between knowing and acting is where momentum quietly disappears.

Sure, timing can swing the other way too: hiring leadership too early, buying tools before the strategy exists, building teams before the product is ready. But today I want to talk about the cost of waiting too long, because I’ve lived it.

The Time I Stayed Too Long

A few years back, I joined a company that brought in a new leader several months after I arrived. I was part of the interview process, gave a thumbs up, and the first few weeks seemed promising.

But around month four, something shifted.

Suddenly, nothing I did was right.

Feedback became criticism.

Direction became contradiction.

The tone became demeaning.

I was getting pinged at all hours, early mornings, late nights, and weekends. The pressure was relentless, and my confidence was dissolving by the day.

What made it worse was how much of that stress I was carrying home.

My husband felt it. My daughter felt it. My parents felt it.

I didn’t recognize myself in that season. But I stayed.

I convinced myself I needed to push through, be resilient, not “give up too soon.”

Meanwhile, staying was costing me far more than leaving ever would.

Eventually, I made the decision to go.

And while the departure was handled as poorly as expected, the relief was immediate.

My only regret?

Not leaving sooner.

How to Recognize When It's Time

Here are a few signals I’ve learned to pay attention to:

1. Early misalignment keeps resurfacing.

Your gut rarely lies twice.

2. Waiting starts costing you energy or momentum.

Stagnation is a clue.

3. You can’t name what improves by waiting.

If nothing gets better, nothing will.

4. Fear is making the decision for you.

Comfort is not clarity.

5. Your life outside work is absorbing the impact.

That’s the loudest signal of all.

6. You’re holding out for the “perfect moment.”

It doesn’t exist.

The Real Lesson About Timing

Here’s what I’ve learned:

• Timing isn’t a detail; it’s a differentiator.

• It’s often the difference between succeeding or conceding.

• Most of us underestimate the cost of delay.

• We assume waiting buys us safety.

But waiting is a decision, and usually not the right one.

When you get timing right, everything moves with less friction: your work, your confidence, your wellbeing.

So whatever decision is sitting on your mind this week…

Don’t wait for the perfect moment.

Honor the power timing has in shaping your outcomes.