#42 | 4 Lessons of 2023 ✍️

At its core, this is a side hustle newsletter. So, I don’t speak about my 9-5 often.

But as 2023 comes to a close, I can definitively say that I’ve learned more at my day job in the past 12 months than any year prior.

I’ve led the pursuit and negotiation of deals as small as a few hundred thousand dollars to as large as $32 million.

When it’s all said and done, I’ll end the year with over $43 million in awarded new business.

Throughout the ups and downs, I’ve kept a running list of personal notes and reminders to myself. Things to do. Things to not do. I find writing these types of learnings down helps to crystalize them.

As I looked back and reviewed them this week, 4 simple but foundational takeaways rise to the top.

I figured I’d share those with you today.

Because regardless of what your 9-5 or side hustle is, make no mistake about it – we are ALL in sales.

1. It’s not a deal, until it’s signed.

“Birds fly. Fish swim. Deals fall through.”

If you had asked me in Q2 what my end of year number would be, I would have confidently said north of $70 million.

I also would have guessed the ink would be dry on a much higher percentage of those contracts.

But guess what? Deals fall through.

Often for reasons completely out of my control. Funding dried up, development plans changed, you name it.

The lesson for me here is not about how to save a dying deal. Instead it’s a lesson in psychology.

The difference between feeling like I “won” $43 million vs feeling like I “lost” $30 million is perception.

One mindset makes you feel good. Motivated even. The other, makes you feel like sh*t and deflated.

Said differently, “You never count your money. When you’re sittin’ at the table. There’ll be time enough for countin’ When the dealin’s done.”

2. Fail faster.

We all know failing is not only acceptable, it’s inevitable.

But what’s unacceptable is knowingly failing slowly.

I spent over 4 months at the beginning of the year trying to make a deal work that I knew in my gut was dead on arrival.

Never again.

We’ve already acknowledged that many of the reasons a deal can fall through are out of your control.

But what often IS in your control is how quickly you recognize a dead deal and cut bait.

So ask the hard questions sooner.

There are only so many hours in the day and deciding to spend time on one deal, is equally a decision not to spend time on another.

3. The power of silence.

A few years ago I was on a conference call with my colleagues from South Korea and one of the more senior team members affectionately referred to me as the “fast talking American”.

It was said in jest, but like any joke with a kernel of truth, it stuck with me.

My challenge to any of my fellow “talkers” out there is this – try shutting the f*ck up.

Seriously.

Go into your next interaction with a client or potential customer with the stated goal to yourself of talking 50% less.

I’m confident you’ll discover what I have. The beautiful power of silence.

As it turns out, when you’re not talking, you give your customer more opportunities to speak and reveal more valuable information to you. Go figure.

And yes, it also means you’ll have to endure some uncomfortable pauses.

But when you get to the other side, you’ll have built constructive tension…something you should be leaning into, not shying away from.

I recently told Mike this and I mean it sincerely – the most successful strategy I have ever deployed in my career came a few weeks ago in the form of a 15-second period of silence on a negotiation call with 13 participants on the line.

It was excruciating.

And it was also exactly what was needed to move the deal forward.

4. Know your role.

I’ve been at the same company for over 9 years now. It shocks me to even type that out.

During this stretch, every 1-2 years I’ve either taken a more senior position or changed roles entirely.

This year I was offered the opportunity to interview for two separate internal positions that could have resulted in meaningful title and pay changes.

If these opportunities had come around any year prior, I truly believe I would have just kept my head down, applied and kept on climbing.

Not this year. And in fact, the decisions were easy.

I had already spent a ton of time and energy thinking about it – long before the interview offers ever came my way.

I had already evaluated my manager and my manager’s manager (who are both incredible by the way) and I had already came to the conclusion that those weren’t jobs or lifestyles that I desire at this point in my life.

I’m enjoying being an individual contributor. I don’t want to manage a huge team again. I’m enjoying being able to spend significant time at home with my family. I don’t want to be on the road for 50% of the year.

I genuinely believe an alarming number of people blindly pursue and accept jobs first and foremost so that they can update their LinkedIn profile.

Don’t be that person. Spend the time and evaluate it now. Your future self will thank you.

I’ll end with this…

In our side hustle world, 9-5s often get a bad rap.

That’s nonsense.

If your day job passes the 80-20 rule (80% enjoy, 20% dislike) and you find yourself constantly learning, keep going.

Have a weekend!! ✌️

-Keith