Welcome to Probation

Hello again, my friend,

Last week, I shared every tip I have for getting a job at a fast-growing startup, like beehiiv. With us hiring, I received so many inquiries that I couldn’t answer everyone (I wish I could, and I’m sorry if I missed you). Instead, I shared everything I did that worked for me, in hopes it would help people land their next gig.

Today, I’ll share how to succeed through the first 90 days at your new job. But don’t worry if you’re seeking a new role, this can help with that too.

The first 90 days are vital because it’s rare for someone who did “just okay” at the start of their new job to go on and get promoted. Believe it or not, it’s common for an employee’s ceiling to be based on that extremely valuable first impression during the initial 90 days.

When you’re done reading this, you’ll be ready to have the strongest, most insane first 90 days. But this isn’t just theory. These are things I actually did myself that worked.

About three weeks after I joined the business full-time, our Co-Founder and CEO, Tyler Denk, shared this with beehiiv’s investors in a private investor update (s/o Tyler).

I hope this helps.

Let’s get into it.

“APM” is an acronym for “actions per minute.”

This is a little nerdy, but I used to play a video game called StarCraft II. In this game, an “action” is essentially any mouse click or press of a button on the keyboard to do something in the game.

I played on my university team (yes, we had esports teams), and we’d often watch pro matches together. We’d debate things like: “Does it matter if they click 300 times if they’re doing the wrong things anyway?”

The same applies to work. Does working 24/7 matter if you’re working on the wrong things or have the wrong priorities? I’ll come back to this shortly.

One thing we noticed was that every pro player had insanely high APM. I’m shocked they don’t have carpal tunnel. It seemed like taking more time to land on the right decision didn’t really work, since nobody in the big leagues did that.

We realized later that it wasn’t like they were spamming buttons with no rhyme or reason. They knew the exact right move to make within a split second of seeing the pixels move on screen. Within that one second, these guys completed five (or more) actions. We’re talking APM over 300.

This analogy applies to work in two ways.

So where do we balance the two? I lean into keeping APM high. Volume, volume, volume of work through the roof.

Not every action will be perfect. But remember, every single pro-level player had insanely high APM. They were winning for a reason. The people who took time to make the right decision weren’t even in the pro league.

While it’s obviously not an apples-to-apples comparison (I hope), this checks out. It’s hard to make quick decisions, and waiting on decisions can be the worst reason to slow things down (nothing happens until a decision is made). Speed forces our brains to decide faster (so as not to block our actions), and over time this compounds better.

The episode of Hey Arnold! in 1996 where Mr. Simmons tells the class, “There are no stupid questions,” was just that. A show for kids meant to inspire curiosity in the classroom. A great thing.

At work, there are stupid questions. But not in the way that you might think. Stupid questions are asking something you could find if you Googled it (or asked ChatGPT) yourself. Try asking AI before you ask your boss. You’d be surprised how many great answers you’ll find without having to ping anyone.

Jokes aside, if you really can’t find the answer, definitely ask. Don’t beat yourself up if you ask a stupid question either, I’ve done it many times.

But there’s another layer to this.

Most people will ask “how do I do this,” and then do it. But what’s actually more effective is to try it, and then say “I did this. Is it good to go, or did you have feedback for me?”

If there’s an issue, your boss will tell you, and you’ll fix it. It’s faster, and what matters in 2026 is the initiative. Forget asking questions just to look like you care or are putting in an effort to learn. The initiative goes a long way. I did this thousands of times in my first 90 days at beehiiv. Still do.

Some people tell you to take time to learn, talk to stakeholders, assess needs and wants, and learn about blah, blah, blah.

Of course, there’s some value in building context by talking and listening. Listening is very important. But in my experience, it never produces results on its own. Going to so many meetings (especially when you first start a new job) is often more about politics or optics.

When I first started at beehiiv, I split myself across all kinds of work. I was answering support tickets, going to sales calls, addressing deliverability, dealing with fraud, banning users who were not compliant, I wrote Creator Spotlight, and the list goes on and on.

Doing this gave me so much context on the business that I could be useful in any situation. To a degree that’s so much more detailed and nuanced than what I could absorb in one or two conversations.

Many small startups are like this: there’s more work than people to do it. You can extend beyond your job description into other parts of the business. If this is not an option for you, that’s fine, you can skip this.

With that in mind, there’s a point where picking priorities is important.

Growing up, it was normal for parents to place their kids in different sports, until the kid found one they liked. We tried hockey, basketball, football, everything. Eventually we’d focus on one.

Work can often be the same way. The small startup grows, lanes are formed, and it’ll eventually be time to specialize. Larger companies do this via their job descriptions. Smaller companies grow into this. But it’s not necessarily the wild west forever.

I eventually specialized on a few core initiatives. This was actually advice I got from our COO at the time. By having a key initiative, project, or major workflow that I’d “own,” I could establish myself within that part of the business. If it did well, it was a lot more than just an individual success, it was company-wide.

If you can turn your initiative into a company-wide win, that’d be a massive first 90 days. Unlikely, but massive.

It costs nothing to be polite, to make an effort, to send a DM, and to say it was a great presentation. Working hard is essentially free up to a point (and that point is well after 8 hours for most of us). There’s no harm in keeping the tone positive.

I always thought being the “personality hire” was an insult. The term was always a joke to describe someone who wasn’t necessarily the best at their job, but was never fired because they were a joy to have around. Borderline insulting yes. But if you’re trying to pass probation and crush that first 90 days, it’s easier if you do these things.

And of course, there are things I’d never do (or do again).

There’s no long list for this section. I’ll describe everything, but in a way that always hits home for me, and it’s actually how work was described to me about 13 years ago when I first started freelancing.

Imagine starting at a new job. You know your job description, the priorities of the business, and you have the tools you need in your cubicle. Your first task is filling out a few forms.

Now imagine sitting there, and doing nothing, until someone taps you on the shoulder and says “go ahead.” So you turn and say “go ahead how?” A lesson begins, it ends, and you try it. It’s alright. You did the first task, and head home.

Then there’s an issue. It’s something you should reply to. You think you should do it. You feel like it’s your thing. But you don’t actually do it. A day goes by. Your boss asks “did you reply?” You say “no, I wasn’t sure if I was supposed to.” They confirm you’re supposed to, and you do. The second task is done, and you head home.

You continue like this for two weeks.

On the 15th day, someone else joins the company and sits in the cubicle next to you. It’s their first day.

They fill out the form, reply to everything, go through the list of tasks. You complete your one for the day, and head home. They don’t go home. They continue working. They leave when all 15 tasks are complete on their first day.

Your boss notices and has to ask how they did it. “I figured if I’m not supposed to do this, you would tell me not to.”

Turns out the work was actually very easy. You just didn’t try doing it.

Who do you think is passing probation?

It’s important to remember that nobody is perfect. Taking time to get things right is valuable. But 2026 is hyper-competitive. And while I got lucky in many ways, I also nailed my first 90 days on the job.

But, it wasn’t because I was the most skilled, or the most technical. I did the things I thought I should (high APM), and admittedly did go a little overboard. Aside from that, it’s really about effort and priorities.

I can’t guarantee this will produce the same impact for you as it did for me. But I’ve seen a lot of people start a new job. The first 90 days are the most important.

I hope this was helpful. If you have any questions, reach out anytime!

Thanks again for reading,

Darwin