“Tell me about yourself.”

I used to cringe when I heard this at the start of every interview. How could I possibly sum up my career history in 2 minutes or less?

I’d done a bunch of different projects, what was I supposed to include?

The classic generalist dilemma.

Being a generalist is a superpower, but it requires another superpower:

Knowing how to communicate your value effectively.

I learned this the hard way during my pivot from consulting to startups. It didn’t make sense to share everything I’d worked on, but rather to carefully choose what’s included in my career transition story.

When I say “story” here, I’m referring to your elevator pitch.

It’s not just what you say to kick off most interviews…

This 2-minute overview becomes your core messaging for the job search.

If done right, it is your cohesive narrative that gets reflected across your LinkedIn profile, resume, portfolio, video intros, and outreach emails (at least, it should be).

The goal of your pitch is to help the audience understand:
(1) why you are qualified,
(2) what your goals are, and
(3) why this role/company/conversation lines up

Crafting a compelling narrative is challenging if you haven’t narrowed in on one role family — because then you can’t determine the most relevant details to include.

Generalists love to target roles that tap into similar skills, but are completely different roles in practice — like Business Operations, Product, and Customer Success for example.

This leads to a lot of energy and time wasted tweaking your story and 158 different resume versions clogging your Downloads folder — while your public resume (aka LinkedIn) becomes mismatched quickly 😢

If you want to have a shot at competing with specialists who’ve been in the same role for the last 4 years, listen up:

You need to clear on the best next move for you and craft 1 compelling story to match.

I know you don’t want to be put into a box as a generalist.

This is NOT about limiting what you can do.

It’s about explaining your experience based on the core problems you solve.

Think of it like packaging up your genius into a nice little gift that others are happy to unwrap.

By the way: If you’re building a fractional career or freelance business, it’s equally important to explain who you help, the problems you solve for them, and your unique way of solving them.

How to craft a compelling story:

1. Define your personal brand

If you don’t define how you want to be known, others will draw conclusions based on pattern matching from their past experience. Start with a personal brand statement that summarizes what you bring to the table.

If you’re not sure what to include, think about:

• What do you want to be known for?
• What do people already come to you for?

You can use a common format like this: “I help [type of companies/leaders you help] achieve [their goals/objectives] by doing [your special sauce].”

For example: “I help B2B SaaS startups beat revenue targets by building influencer marketing programs that win customer mindshare.”

Use AI to iterate on this! Claude's my favorite for this. Feel free to use metrics too if you want to include your best proof point.

When I was pivoting from consulting to startups, I didn’t want to simply summarize my consulting experience, so I emphasized what I was excited about working on next.

2. Tap into Selective Storytelling

Your story is the bridge between your now and your next. Share only the relevant details that support that bridge.

Remember: your audience only knows what you tell them. When you are selective about what to include, it sounds like all of your experience lines up perfectly. BOOM.

Use the Rule of 3: Choose your top 3 most important experiences that directly connect to where you want to go. Save the rest for your interview stories. Focus on the impact you drove. Bring your skills to life with examples and quantifiable results where possible.

When I was pivoting to startups, I didn’t talk about every project or role in reverse chronological order. I highlighted my top 3 experiences where I demonstrated skills aligned with the role, such as these:

• Worked with early-stage companies
• Solved ambiguous problems with limited resources
• Built new processes from scratch
• Collaborated across functions to drive results

I spun the most relevant experience I had to benefit my pivot (intrapreneurship and bringing 0-1 offerings to market), and simply left out my less relevant experience (like change management for a banking merger).

3. End with Your Why

After you share your top 3 most important past experiences, bring them back to today. Share what you want out of your career next.

Highlight your skills & how you’ll use them to help the company achieve their goals:

“Next, I’m looking to bring my skills in data analysis, strategic thinking, and project management to help an early stage startup scale operations in new markets. I’m excited to roll up my sleeves and dive into the data to inform launches.”

If you’re actually delivering your pitch to a specific company, reiterate how this opportunity perfectly lines up with your goals. You’re being intentional – let them know it.

This is how you craft a compelling narrative that illustrates why you’re qualified for your next move.

Here’s the kicker: Having a great elevator pitch is step 1 of building your positioning.

The magic happens when you know how to bring that narrative to life – across your LinkedIn profile, resume, portfolio, video intros, outreach, networking chats, and especially in interviews.

This newsletter issue was adapted from my free email course: The Generalist Career Transition Playbook. I share all of my proven strategies to unlock your next energizing career move as a generalist in 2025. If you haven't taken it yet >> Grab it here.​

Let’s win together,

P.S. If you’re feeling stuck in your job search, I guarantee this is an area to refine (likely along with your targeting). I helped 4 members of The Accelerator craft their pitch in the last week. Reply “READY” to see if you’re a good fit to join us. February slots are filled, but March is opening soon.