Some Career Lessons I Apparently Needed to Learn 14 Different Times

I didn’t build my career through some perfectly mapped-out plan. (Which is actually kind of surprising, seeing as I try to help others map out this plan as a career.)

I ultimately arrived here by getting dropped into messy situations and figuring things out in real time.

Small teams. Big personalities. Tight budgets. Founders trying to hold 97 things together with pure force of will.

Somewhere along the way, startup work started beating a few lessons into my brain.

Some of them I learned quickly.

Some of them I apparently needed to learn over and over and over again.

So in honor of that… here are a few things I learned the hard way over 15 years working inside early-stage companies.

(You’re welcome.)

Speak up earlier than feels comfortable

Early in my career, I thought confidence and experience were the same thing.

They are not.

Some of the loudest people in the room were also the most wrong.

I can still remember sitting in meetings, feeling physically uncomfortable because I KNEW something would become a problem later.

A customer workflow that made no sense.

A launch timeline that was never going to hold.

A process everyone was nodding along to that absolutely nobody was going to follow once real life hit.

I stayed quiet sometimes because I assumed everyone else knew more than me. (If you truly know me, this is out of character. I tend to let my thoughts be known. 😂)

Older.
More technical.
More experienced.
More important.

Then I got to watch the exact problems I was worried about happen anyway.

Over time, I realized something really important:

Speaking up thoughtfully earns more respect than silently being correct.

People trust operators who are willing to say:
“Hey… I think this might break later.”

I actually think a lot of leadership teams are desperate for someone willing to say the uncomfortable thing calmly.

Sometimes being right is not the most important thing

This one took me YEARSSSSS.

Especially as someone who really likes being correct. (Hi. Hello. One of my larger faults.)

Startup work taught me that you can be completely right and still make the situation worse.

I’ve built processes that founders immediately changed three days later.

I’ve watched teams resist systems that were objectively cleaner because they were exhausted and overwhelmed and couldn’t absorb one more change.

I’ve sat in meetings knowing a decision wasn’t the best possible decision… but also knowing the team needed momentum more than another week of debate.

That’s the thing nobody tells you about operations work:

You are not optimizing for intellectual victory.

You are optimizing for progress, trust, clarity, and morale.

And in small startups, especially, morale IS infrastructure.

If every conversation becomes about proving who was right, people stop collaborating and start protecting themselves.

Sometimes the best thing for the company is swallowing your pride, adjusting course, and helping the team move forward anyway.

Even when you know your original recommendation was better.

(Annoying lesson. Hate that one for us.)

Nobody is coming to fully train you

I used to think everyone else had some secret handbook I missed.

Turns out most people are figuring it out in real time, too.

Some of the most important things I learned happened in rooms where I barely said a word.

Board prep meetings.
Fundraising conversations.
Sales reviews.
Customer success escalations.
Hiring discussions.
Budget conversations.

If someone gave me the option to sit in on something, I almost always said yes.

Even when I didn’t fully understand half of what was happening yet.

That wasn’t the point.

Repetition changes your baseline.

The conversations that once intimidated you eventually become conversations you can contribute to.

The people who level up fastest are usually the people paying attention long before they “need” the information.

I also learned how rare truly generous mentors are.

There are people who gatekeep knowledge because it makes them feel valuable.

And then there are people who pull others into the room and say:
“Come listen. You’ll learn.”

I never forgot the difference.

Which is exactly why I try so hard now to help younger operators and founders coming up behind me.

Finding someone willing to explain things without making you feel stupid is a massive gift.

Simplicity scales better than brilliance

I have watched companies spend THOUSANDS of dollars building systems nobody actually uses.

Beautiful dashboards.
Overengineered workflows.
Fancy project management setups with seventeen automations and color coding and ten different views.

Meanwhile everyone is still slacking each other:
“Wait who owns this?”

Startups love building processes for their fantasy selves instead of their actual teams.

If you haven’t been listening to me blab enough about this allll over social media, lemme just say it again, the best systems are usually a little boring!

Clear owner.
Clear next step.
Clear due date.
Clear place to look.

That’s it.

The companies that scale best are not always the most sophisticated.

They’re the ones where people consistently know:
who is doing what,
where information lives,
and what happens next.

Honestly, “stupid simple” scales surprisingly far.

Final thoughts from someone who has absolutely learned many things the hard way

I still learn lessons the hard way constantly.

Startup work has a very humbling way of finding your weak spots.

Looking back, most of my career was built from:

paying attention,
staying curious,
speaking up,
asking questions,
and trying to make complicated things a little easier for the people around me.

That’s still the job.

And for anyone earlier in their career reading this:

You do not need to know everything yet.

You just need to stay curious enough to keep learning.

That part matters more than people think.

KB

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PS: If your company currently runs on tribal knowledge, founder memory, and Slack archaeology… hi. You are exactly the kind of team I help.

I work with early-stage founders to simplify systems, clean up operational chaos, and build processes people ACTUALLY follow.

I currently have 2 open spots for embedded fractional COO support.

If your team is growing faster than your operations can keep up, let’s talk.