Last day of the year and I’m spending it here in Disneyland with my wife and family! It’s been a few years since my last visit to the “happiest place on Earth,” and it felt so nice to come back without needing to hit every single ride.
And excuse me while I relate my Disneyland day back to real life but I think that’s the ideal way to live out our career… not rushing to hit every single checkbox.
I’ve never been great at dissecting my year and making year-end reflections, but the more I think back to this year (and previous years), I find myself the happiest when I am just going with the flow. Now, of course, I love a good grind sesh with my team and being so deep in my projects that I forget what time it is, but working hard just for the sake of working hard doesn’t appeal to me as much these days.
As I am getting older, I want to be present. I want to do things as they come. I want to enjoy the day and enjoy the people I am with.
And that’s what a good day at Disneyland feels like.
So that’s one of my goals for the new year: to spend more of it at ease and go with the flow of what’s to come. I’d love to hear from you — are you entering this phase of your life as well, or in the build mode of that ideal career?
Rooting for you,
Sho
P.S. We want to start the new year in style with our FREE 2-Day Job Search Bootcamp! You can RSVP and save your seat here, and let’s get your “new year, new me” started right!
We are all obsessed with the “Timeline of Financial Success,” and it’s quietly messing with our heads.
As the year wraps up, I feel like most of us are doing the same mental audit and asking:
“Am I where I’m supposed to be by now?”
We scroll online, talk to family, or catch-up with friends and ofc it’s expected to hear career + money talk. And I think this is why internalize this idea that by a certain age, we should hit certain financial milestones or else something we failed.
Here’s my hot take: F*ck the numbers and where we “should be.” The only way they may be helpful is if we solely use them as references.
Because our traditional workplace treats them like a winning scoreboard…
By your 30s, you should be “established.”
By your 40s, you should be “accelerating.”
By your 50s, you should be “secure.”
And if you’re not? Society quietly labels you as “behind” or “failing.”
But is this expectation of “success timeline” actually doable? Ok, let’s ground this with reality for a second, using median numbers (not averages inflated by billionaires):
The 30s or The “Building” Decade
The real focus here is learning how money works, negotiating pay, and building habits that compound.
Median salary (ages 25–34): ~$55,000
Median net worth: ~$39,000The 40s or The “Acceleration” Decade
This is where income usually peaks and strategy matters more than hustle.
Median salary (ages 35–44): ~$72,000
Median net worth: ~$135,600The 50s or The “Maximization” Decade
The focus shifts to preservation, flexibility, and choice.
Median salary (ages 45–54): ~$71,600
Median net worth: ~$247,200
So it’s up to you and how you use this data. If you think doable or too easy? More power to you!
On the flip side, if these numbers don’t make you feel good, don’t look at em!
Because you know this if you follow me: Your career is your career, and growth does not move in a linear slate.
Keep going, even when it’s messy!
Salary Transparency Is Here to Stay: With more states and cities enacting pay transparency laws, companies are being forced to disclose salary ranges in job postings. This is a massive win for employees, giving you more leverage in negotiations and helping to close the wage gap.
The Disappointing Year-End Bonus: If your bonus felt a little light this year, you’re not alone. Many companies are tightening their belts. But don’t just accept it. Instead, use it as a reason to schedule a conversation about your performance and compensation plan for 2026.
Your LinkedIn Is Your New Resume: Recruiters are sourcing talent directly from LinkedIn more than ever. Be sure to update your headline to be a value proposition (e.g., “Helping SaaS companies scale their content marketing”) rather than just your job title.
The hottest trend in benefits isn’t new facilities in the break room. It’s time. As burnout remains a huge issue, forward-thinking companies are embracing a four-day work week.
This isn’t just about a long weekend. Studies have shown it boosts productivity and employee well-being. Here are a few companies leading the charge:
Kickstarter: The crowdfunding platform has been a vocal advocate for the four-day work week, proving that you can still be highly successful while giving employees more time to recharge.
Bolt: The tech company adopted a four-day work week and reported that 94% of employees and 91% of managers supported the policy change.
Buffer: A pioneer in remote work, Buffer has also successfully implemented a four-day work week, focusing on asynchronous communication and deep work to maintain productivity.
This book is a superb cheat code for how you show up at work, in interviews, and in rooms where decisions get made.
I love how Vanessa breaks down something most of us were never taught. It’s not just what you say, it’s the cues you send while saying it. Your tone, posture, expressions, and even your emails shape whether people trust you or tune you out.
Plus, this isn’t the usual vague “be confident” advice. It’s practical, clear, and immediately usable. If you’ve ever wondered why your ideas don’t land or why you get talked over, this book gives you real answers.
You feel like you’re doing great work, but it’s not always being recognized or taken seriously.
You want to sound more confident in interviews, presentations, or negotiations without faking a personality that isn’t you.
You’ve been interrupted in meetings, overlooked for opportunities, or felt like your ideas get ignored.
You want practical tools to improve your presence, influence, and credibility at work.
You’re aiming for leadership roles, client‑facing work, or higher‑stakes conversations and want to show up stronger.
Audience Question:
“What if I have no prior work experience at all (no other job offer), but their offer is not enough to live of [sic] the big city.”
– (@Gildedsunflowerboat, from YouTube)
This is a tough but very common situation, especially when you’re starting out. The first thing to remember is that even with no experience, you have leverage because they chose you. They see your potential. The biggest mistake is to either accept a low offer out of fear or to give a hard ultimatum that gets the offer pulled.
You want the negotiation to feel like a win-win. Here’s the play:
Start with Gratitude, Not Demands: Always begin by thanking them for the offer and reaffirming your excitement for the role. This shows you’re a partner, not an adversary.
Use Research as Your Anchor: Since you don’t have a competing offer, your anchor must be based on market data. Do your research on what a fair salary is for this type of role in that specific city.
Stop and Listen: This is the most important part. After you make your ask, stop talking. Let them be the next one to speak. This is a key negotiation tactic. More often than not, they will come back with a revised offer or open a discussion.
The key is to frame the conversation around the market value of the role itself, not just your personal needs. It shows you’ve done your homework and are approaching the conversation professionally.
Negotiation is a skill, and I break down the psychology behind it in my video on proven negotiation hacks. Watch it to learn:
If this is also happening to you, go listen to other Ask Sho segments in this full podcast episode:
Watch the full episode here: How to Negotiate Salary After a Job Offer (3 Proven Hacks)
Got a career Q that you want to me to answer? 🤔
I’m starting a quick Q&A series where I answer real questions every other week.Ask me about job stuff, interviews, resumes, awkward convos w/ your manager…
I’ll help you figure all of that out!
Just drop a (3–5 sentences) comment or DM me your situation and how I can help.
If you want it anon, just say so. Let’s get into the good stuff.
Save your seat to our brand new, FREE Job Search Bootcamp on January 7 & 8! It’ll be jam packed with all our best stuff on interviews, negotiations, and everything you need to get hired & paid in the new year. See you there!
If you need career-related advice or got some stories to share, send them here or email them to: support@workhap.com.
For more content, follow me on social media: Sho Dewan in LinkedIn and @workhap in Instagram, Facebook, Tiktok, and Youtube
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