Angeliki's Messy Middle Career Update
The week of prep, editing & delivering
Last week was a proper ‘a chaos in my messy middle’ week. Loads of editing and social media repurposing for the new episode that went live on Friday. Alignment calls with the new guests I’m filming with topics on Building a Portfolio Career and Personal Finance 101 coming in September. I also delivered two client workshops: one B2B in-person on personal branding (still have an impostor syndrome on this one) and a B2C virtual on using AI for accelerating your personal brand.
I also had to make a tough call. I turned down a two-month "podcast growth engine" paid package that would've handed the whole thing over to an outside team and freed up my summer. On paper it looked like acceleration. But I got scared with the cost (though a good deal!) while I don’t have a stable income. I keep struggling to balance paying ahead, investing, accelerating my podcast, with my “don’t spend the money away” and I honestly don’t know what’s the right way to go…
Finally, I somehow managed to make a lot of time for friends, a half day at the pool, and taking Friday off for a long weekend to Spetses (an island close to Athens, super cosmopolitan and fun). ps. Don’t go with a dog, there are horses everywhere and my dog didn’t like it. 😂
Communication & Personal Branding Tip of the Week
Climb Cringe Mountain 🏔️
Between where you are now and where you want to be (the new career opportunity, the visibility, the side hustle) there's a mountain to climb. Alicia Teltz calls it Cringe Mountain: being seen publicly trying, stumbling, figuring it out in front of people. The ones rolling their eyes at you are stuck at base camp. The ones cheering you on are climbing too. You only need the second group. And this advice is what helped me less than a year ago to go all-in on LinkedIn without cringing with myself (at least not so much), or at least not stopping me from posting. Because you never know where the next opportunity finds you.
"To get to the land of desire, you have to climb Cringe Mountain: being publicly seen trying and potentially failing. The people rolling their eyes are stuck at base camp and they would like to do what you do." — Alicia Teltz, Episode 06 from my podcast.
the cringe mountain you have to climb to win on the other side
Career Insight of the Week
Your CV is the least important thing in our job search
Your CV is only 20% of the story. You are the other 80%.
Two things to do with that:
Stop writing your CV like a job description. Don't list what you were hired to do. List what you actually accomplished and want to be known for next. And drop the AI-perfect corporate speak ("motivated, self-driven team player"). Every CV now reads identically, which sets off a recruiter's radar. Sameness reads as fake. Real, specific, slightly imperfect wins.
Bin the cover letter. Sean's read maybe four worth reading in over a decade. "Dear Sir or Madam" and he's out. After you apply, message the recruiter on LinkedIn instead:
"Hi, I've applied and I know that's the process, just wanted to share a bit about me to help your decision, since not everything's on my CV.
(xyz short and sweet)
If there's anything that'd help me stand out, happy to answer it. And I'd love to learn more about the business this week if you're free."
Warm, human, a little vulnerable. It shows effort 99% of applicants never make and it's usually what gets you the interview. Because just hitting apply doesn't earn you one. 👀
This came straight out of the latest episode of my vidcast, The Adaptive Times. I have to credit the wisdom to Sean Kennedy.
Podcast Guest of the Week
Meet Sean Kennedy

Sean is a Tech Recruiter and LinkedIn Content Creator. He shares his wisdom from his 12 years in Talent Acquisition with a fun spin off. Def a good vibes episode this one…
We cover ALL things job search in the current market. YES, with all the difficulties we have to navigate head on.
Watch the full episode on YouTube or listen on Spotify:
AI Hack of the Week
Brief like it’s a human
The reason your prompts fall flat is usually that you're skipping the context you'd give a real person. Think of the following structure:
1. Task: what you need done, end goal and current process
2. Audience: who the output is for and what they care about
3. Context: documents, background, what "good" looks like, your tone of voice if it’s a written output, etc. something that is YOU
4. Constraints: format, length, tone, and what NOT to include
Bonus: instead of asking for one version, ask for three of a good one. Also, a bad one. Then iterate on the best one based on the understanding you now have of its range.
That’s it for this week.
Go pick your mountain and I’ll be watching you climb.
What topics you would like to see more of: career insights, podcast written summaries, AI hacks, mindset shift tips or effective communication frameworks? Or my own journey learnings?
Hit reply and let me know. Forever grateful.
Stay adaptive. Stay curious.
Angeliki

