🦝 His career "plan" kept falling apart.


A lot of people who read GradSimple are stuck.

Genuinely stuck, where you've looked for answers, tried things, and still can't seem to move forward in a meaningful way.

And I really want to know the specific reason why you're still stuck despite trying.

Is it that you've found advice but have no idea who to trust, so you end up paralyzed trying to figure out what's even true?

Is it that you understand the advice but can't figure out how to apply it to your specific situation, your degree, your background, your market?

Is it that you know what you need, a mentor, a referral, a real conversation with someone in your field, but you have no idea how to get access to that?

Is it that you've tried before, it didn't work, and now every new attempt feels pointless before it even starts?

Or is it something else entirely that I haven't mentioned?

I'm asking because the whole point of GradSimple is to make things easier for people trying to figure out their careers. But I can only do that if I understand the real reason things haven't clicked yet. Not just what the problem is, but why you haven't been able to solve it.

Hit reply and tell me. What have you tried, and why do you think it hasn't worked?

I will personally read and respond to you within the next week.

— Tyler


⭐️ Humans of GradSimple: Hassan S.

Hassan has done a bit of everything since finishing his degree. Substitute teaching, commission-only sales, tutoring, working with his dad, even learning how to look for jobs. It hasn’t been linear, and it hasn’t been easy.

At one point, he stepped back entirely to ask himself a tough question: instead of what can I do, what do I want to do?

Now, the challenge isn’t effort. It’s translation. Knowing he’s good at connecting with people, motivating them, showing up in conversations, but is struggling to turn that into something a resume or application can capture.

It’s that gap between what you know you bring, and what the system is set up to recognize.

"My value has always been being in front of people, being able to capture attention, connect with them, and motivate them to do things...I’d really like to be in front of more people again, I’m just not sure how to make that intentional instead of it being these sort of drive-by conversations I’ve had in the past."

Do you need to be clear on your path before moving forward, or does clarity come from just taking the next step?


⭐️ The Pivot Report

A hiring insider's take on how people get from where they are to where they want to be.

Teaching is one of those careers everyone has an opinion about. "You'd be so good at it." "You get summers off!" (You don't really, but okay, sure.)

Teaching, whether you're subbing, tutoring, or running your own classroom, is incredibly demanding. It drains most, but for some (if you’re a saint), it’s one of the most fulfilling jobs out there. If you can handle it, big ups to you.

Here's what I see show up regularly.

1. You have to actually like people. Yeah, I know…shocking. But I have to say it! Not in the abstract "I care about the next generation" way. In the real, concrete, someone-is-talking-to-you-for-the-sixth-time-today way. Teachers who last are the ones who find those interactions genuinely interesting. If you need quiet to recharge, a classroom is going to be a hard place to spend eight hours.

I’m not saying you can’t be an introvert, but a lot of the best resumes exemplify strong interpersonal skills.

2. The structure (or lack of it) might get to you. Substitute teaching sounds flexible until you realize "flexible" means unpaid gaps and zero guaranteed hours. Tutoring platforms look better on paper until you're logged on, unpaid, waiting to be matched with a student who may or may not show up.

A lot of hiring is focused on contract work or per diem. But hey, that can actually be a good place to start gaining experience.

What have we learned? To put a bow on it, teaching is a field that rewards people who connect naturally, but punishes people who don't have a plan beyond "I like helping." Passion fills the first few months. Systems and sustainability carry you through the rest!

Coffee helps, too.

If you read this and some of it caught you off guard, that’s not unusual.

Most people only realize these things after they’re already in the job.

Teaching is one example, but the same pattern shows up across a lot of careers. What looks good on paper often plays out very differently in reality.

If you’re deciding between a few paths right now, or thinking about pivoting, this is where having the right context matters most.

Inside GradSimple Insiders, we break down different paths like this every week so you can see what you’re walking into before you commit.

See what you're walking into →

— Grace


How's finding your career going... really?

If you’ve been stuck in your head, you’re not alone.

Most people we talk to are overthinking a decision, second-guessing their path, or unsure what to do next.

Being a Human of GradSimple is a chance to actually talk it through with someone who gets it.

And almost everyone says the same thing after:

“I didn’t realize how much clearer things felt just saying it out loud.”

If you’ve been going in circles, this might help more than you think.

Tell us what you’re going through →


👀 Ricky Brain

Top posts from our YouTube and TikTok! Ur welcome.


P.S. Don't forget to reply to this email and share: Why do you think you're stuck? What have you tried, and why do you think it hasn't worked?

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