I'll be perfectly honest with you! I procrastinated writing this newsletter until an hour ago.
We've been rethinking the DNA of our newsletters. As Grace mentioned last week, we've become too stiff and "proper."
We went from writing as a literal feral raccoon (shoutout to the OGs who know Ricky) to cranking the dial 180 the other way. I think we need to find a better balance of being helpful, but not taking ourselves too seriously.
When I sent our very first email in 2024, I vowed never to be "corporate." I'd hate for us to be just another boring, soulless career advice resource. That suuuucks.
So let's get back to our roots. Who cares about being professional?
From now on, Grace and I will write as our true selves. There may (will) be more rambling. I may be a little unhinged at times. Share tidbits of our lives.
Lean into our weirdness, ya know?
⚖️ It's a poll! Please respond so I know someone is reading this.
Idk about you, but networking is terrifying to me.
I guess you can say I network a lot, doing GradSimple. But it's far from second nature to me. Every single time, I'm stepping outside of my comfort zone.
My heart rate speeds up, my palms get sweaty, and sometimes, my tummy aches. Still.
I'm just very good at hiding it now.
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We have a super useful article on this exact topic, btw.
🧠 Tyler's Take: Your career growth might depend on this
Inspired by last week's Human of GradSimple, Jordan M.
My younger self only cared about money.
If Company A offered me more money than Company B, I’d join Company A in a heartbeat.
Things like culture, location, work-life balance, a company’s trajectory, the people I’d be working with, and the industry didn’t matter much to me. I was a mercenary to a fault.
I know, I know. I'm not like that anymore. I’ve learned the hard way that salary is only one piece of the puzzle. There are a lot of factors that influence whether an opportunity ends up being good for your career and life.
Over the years, I’ve realized there’s one factor that doesn’t get talked about nearly enough: whether a company is growing.
It influences how quickly new opportunities become available, whether you can take on more responsibility, and how fast your career can progress. Jordan’s story reminded me of this.
She made the observation that many companies expect employees to spend a certain amount of time in a role before progressing.
What’s interesting is that progression isn’t always tied to capability. More often, it’s tied to things like tenure, promotion cycles, budgets, and whether there’s an open role to move into.
At many larger organizations, there are job levels, approval processes, promotion cycles, and headcount constraints. Even if your manager thinks you’re doing a great job, there may simply not be a path available yet. The next role might not be open. The budget might not exist. The team might not be growing.
This is a big reason why I’ve always found startups interesting.
When a company is growing quickly, problems appear faster than people can solve them. New customers need support. Processes need to be built. Teams need to be formed.
Growth creates opportunities, and someone needs to step into them.
I’ve seen people take on responsibilities that would have required multiple promotions elsewhere. And often, it’s not because they were dramatically more talented than their peers. Their company was growing, and they happened to be in the right place at the right time.
Of course, startups come with their own tradeoffs. You’ve probably heard the cliché about wearing many hats. Some are pure chaos. Some fail. Some provide very little structure or support.
But I think many people underestimate how much company choice influences career outcomes.
Two people can be equally capable and equally hardworking. One joins a company where progression is slow, structured, and predictable. The other joins a company that is doubling in size and creating opportunities as it grows.
Three years later, their careers can look completely different.
When people evaluate jobs, they usually focus on the role, salary, benefits, or company brand.
I think they should spend more time looking at whether the company itself is growing.
The more people I interview, the more I realize that career progression is not purely a function of talent, effort, or ambition.
It’s also heavily influenced by the environment you’re operating in.
Sometimes the fastest way to grow your career isn’t to work harder but to put yourself in a place that’s growing too!
Pss... Share this with your best friend.
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Gus Baxter has worked with 500+ students at Drew University. He's also a trained executive coach. His verdict? Job seekers waste months doing the one thing that matters least. Next week, Insiders get the uncut conversation.
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😋 Career Snack: Instructional Designer
Most people have sat through a soul-sucking training that made them want to fall asleep.
Someone built that. And someone could have built it better.
That's basically what an Instructional Designer does. You're the person responsible for making learning work. Onboarding programs, online courses, certification modules, and compliance training. Any organization that needs people to understand something hires for this. Which is nearly every organization.
Day to day, you're translating complicated information from subject matter experts into something a typical employee can absorb. You build it out in tools like Articulate, Ivy League, or Workramp. And then you figure out whether it landed.
The people I think are built for this: patient, detail-oriented, genuinely care whether the person on the other end gets it. You probably explain things well and have been told that your whole life.
Avg starting salary: $50,000 to $65,000. Climbs to $80,000+ with a few years of experience.
AI Resilience Score: 7/10 🟡 AI is changing this role but not replacing it. Tools now handle a lot of the content drafting and module building. What they can't do is understand learners, manage stakeholders, or make judgment calls about what works. The designers who learn to work with AI tooling are becoming more valuable, not less. The ones ignoring it are getting left behind.
P.S. If you have any feedback, ideas, or things you want me to write about, just reply to this email. It goes directly to my inbox, and I will respond within 48 hours.
Life is rich,
⎻ Tyler
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