3 Career Stages and how to Succeed in Each

Different stages of a career use different tools, so you need to build your career at each stage with the appropriate tools. 

Here’s what I’d focus on in 2026–2028, depending on where you’re (and this works for job seekers, too). Feel free to skip to whatever section applies. Otherwise this will be a pretty long read. 

Key skills:

• Communicating your value without sounding arrogant
  • Chances are you’re young. Own it rather than trying to it speak around it. You aren’t fooling anyone by getting defensive, or by talking about how great you’re at the field already. 
• Knowing how to integrate AI into the field
  • Not just the basic models like ChatGPT, either. That isn’t good enough anymore. Like it or not, AI is going to change every single industry. You can fight it, or you can use it. Senior leaders want to integrate AI. They’ll want people who can help them do that. Just don’t use it in your own job search too much.
• Learning to quantify your impact
  • Even small wins matter, and you aren’t expected to know everything. Build this impact through internships, summer jobs, working during the school year, etc. These will give you numbers to provide on your resume.
• Being the best learner
  • Curiosity is attractive, especially at the entry-level. You want to come across as highly teachable. It activates in others their desire to help, and speaks to their ego as well. They feel special. 

Hiring managers aren’t betting on potential alone anymore. They’re betting on people who prove they can learn fast and produce clarity, while remaining teachable in attitude. The last one is arguably the most important.

Key skills:

• Translating your experience into business outcomes
  • This is probably the hardest part for pivoters. I’ve had a couple clients now who have looked into pivoting from different medical fields into something entirely different (graphic design in one case, and consulting in the other). The key is is to leverage your unique perspective gained from the other field. Traditional applicants won’t have that.
• Mapping job descriptions to transferable skills
  • Selling a transferable skill seems daunting. “How do I even talk about that?” is a pretty common question I get when coaching someone. This can be pretty hard to determine on your own at first, but once you’ve seen it applied a couple times, you start to think outside the box. For example, I had a client who started his career as a nurse. He then pivoted into photography, and was trying to break into graphic design when he started meeting with me. I pointed out how the bedside manner he’d been trained to have in nursing paired with his natural caring and empathy, which helps him see problems clients have before those clients become frustrated (and in some cases before the clients even really feel those problems). After that, it clicked and he took that forward into other applications.
• Micro-proof: small wins that signal capability
  • Your direct experience will be eerily similar to someone coming fresh out of a degree program in the field you’re targeting. So you need to work past managerial doubt that your experience matters. Ageism can come into play a bit here too. Focus on the small connections between the two fields and what you’ve already done.
• Thoughtful storytelling — not desperation
  • Telling a story (well) is remarkably powerful. Again, the key here is translating your own work stories into what people care about in your intended field. You’ll lose them in too much technical detail, but you should provide relevant detail. Names, timelines, and quantifiable outcomes will always translate.  

Pivots fail when they sound like reinventions instead of reallocations of value. You’re trying to connect who you were to who you want to be. You bridge the gap rather than try and leave your past behind. 

Key skills:

• Delegation without dumping
• Leading without authority (first)
  • Everyone has the potential to lead, and in fact, the best leaders don’t use formal authority very often, if at all. Signal that you’re a great leadership candidate by being helpful, an expert, looking out for the wellbeing of others, and building up everyone around you (even your leaders).
• Coaching instead of correcting
  • Again, don’t rely on your authority whenever you can help it. The key difference between coaching and correcting is to provide explanation and warmth rather than coldness. Think, “this way might work better given X,” instead of, “do it this way.”
• Strategy → prioritization → execution
  • You’ll need all three to be a leader, but the first thing you need is strategy (knowing where you’re going and how to provide value in a way others can’t). Increasingly this will integrate AI into the mix.

Leadership isn’t a promotion so much as an identity you build before the title finds you. At least, that’s what we’ve found characterizes our favorite leaders; those who don’t rely on a formal position because they’ve been leading without one for a while, and have learned to be genuine and build their followers.