3 Steps to Landing Your Dream Job, Promotion, or Business (Especially Later in Your Career)

I’ve had hundreds of coffees with execs, coaches, and Big Tech professionals, and here’s the brutally honest career advice no one wants to hear.

1. The Advice You Know but Aren’t Doing (Let's Be Real)

It’s wild that we spend half our lives working but rarely invest in improving our job-search skills after college.

We all know exactly what we should do, but let’s be honest, almost nobody actually does it. We complain about how hard we're "looking," yet conveniently skip the basics: regular networking, interview prep, or directly asking friends about open roles.

Seriously, high schoolers and college students effortlessly do mock interviews and attend industry events, while professionals often think they're beyond this. Trust me: if you haven't practiced interviewing lately, you're probably rustier than my guitar playing after it spent a year gathering dust.

Swallow your pride, take the ego hit, and commit to real practice. We do this in all other areas of life, from personal training, to masseuses, to even getting meal prep. If your struggling with accountability, work with a close friend or mentor in your space. If you don't have one or are too shy to ask for help, hire someone, like a coach.

2. The Advice You're Doing but Shouldn't Anymore (STAR is Dead—Sort Of)

In the age of AI, Zoom fatigue, and endless interview prep, everyone's STAR method responses have become overly rehearsed, borderline robotic. Interviewers instantly sense your scripted approach, especially when you kick off with a mechanical "The situation was...". Worst of all, if you do this too much, most interviewers will assume you are reading off of a script, which will send off alarm bells and instantly get you a "Do Not Hire" in the system

Instead, share genuine stories. Let me give an example. Normally I tell a story about how I won a client as a first year at Deloitte to illustrate my drive and interest in business. Would you prefer that, or a robotic reciting a STAR scenario - The situation was I wanted to win business so I could have a tech client, the task was I sent cold emails to over 1,000 prospects, the action I took was a series of awkward coffee, and the result was I eventually won a client in the space.

Authenticity resonates more deeply than any memorized script ever could.

Bottom line: Toss out the bullet points and speak naturally. Ask yourself honestly: Would you rather hire a walking STAR-method encyclopedia or someone authentically excited about their work?

3. The Advice You Probably Haven’t Heard (But Should Have)

Here's a crucial yet overlooked truth: No amount of interview prep beats genuine alignment between job and personality. Many seasoned professionals choose roles purely based on convenience, salary, or because it's the first offer, especially during tough hiring periods.

Instead, ask yourself:

• Does this genuinely align with who I am and my long-term vision?

• Is this decision beneficial for my family, lifestyle, and long-term happiness—not just my resume?

• Could pivoting or trying something new open even bigger doors?

Nobody enjoys feeling like a beginner again, but real growth often requires stepping into new spaces. Who ultimately has greater career potential: someone narrowly specialized for decades or someone who combined experience in accounting, sales, and strategy consulting? Diversifying your skillset, even later in your career, often leads to significantly greater opportunities.

If you can’t pivot because your lifestyle won’t let you… maybe it’s time to ask whether you own your life, or your lifestyle owns you.

Final Thought (Yes, Action is Required!)

It’s never too late to shift gears, refresh your approach, and embrace growth—even if that means temporarily feeling uncomfortable. Your dream opportunity isn't going to appear through repeating old patterns; it's found through authenticity, strategic networking, and thoughtful pivots.

If you're feeling stuck or simply need someone to talk this through—reach out. Whether you need executive coaching, career guidance, or just casual advice over coffee, I’d love to help you unlock your next big move.