Creating Career Dots

I’ve watched Steve Jobs’s 2005 Stanford commencement speech more times than I can count. It’s filled with insight, but one quote always resonates:

> “You can’t connect the dots looking forward; you can only connect them looking backwards.” - Steve Jobs It’s true for life. And it’s especially true for our careers.

If you’re reading this, chances are you’ve been laid off. That experience likely disrupted a path you’d been building. You did the right things, made an impact, contributed to the team... and now you’re left trying to figure out where to go next.

The Linear Fallacy

Growing up, we were taught to plan our careers like they were fixed destinations. I remember taking a career survey (personality assessment) in high school that told me what college major to pursue… which would lead to a job… which would lead to a career. That was the formula.

But that formula assumes one job title, one field, one industry. And unless you're in a highly specialized track where depth is everything, like medicine or law, most of us are constantly adjusting and adapting. The world moves too fast to stay on one track.

In my opinion, we must be open to change now more than ever.

Optionality

Said differently... creating new pathways to succeed when things don’t go according to plan.

The same applies to us. Optionality is career leverage. And in your job search, optionality comes from creating dots.

As Jobs inferred in his commencement, dots are conversations, experiences, ideas, and risks that expand your future possibilities. They might not pay off immediately. But when the time is right, they connect... often in ways you couldn’t have predicted.

So don’t just "plant many seeds" (i.e., apply to more jobs). Create dots. Dots open new doors. Dots enable pivots. Dots become leverage.

How to Create Dots (3 Practical Ways)

Last week, I shared on LinkedIn about how, at 24, I cold-emailed the CEO of a multi-billion-dollar company and asked him for coffee. We never got that coffee. But a few weeks later, I was invited to a leadership roundtable and sat between two Directors who later became my bosses. That one bold ask didn’t lead to what I expected… but it led somewhere better.

Action: Reach out. Be bold. Get yourself in rooms with people who can open doors, even if you don’t know how yet.

2. Apply for roles you're not "qualified" for on paper.

When I interviewed for my last role, Director of Product Management & Development, I told the VP, “I have zero Product experience on my resume.” But I laid out how my background in strategy, marketing, and business development gave me all the tools Product requires. That leap was an unexpected connection of dots.

Action: Apply to 20% of roles that are a stretch... roles where your skills make sense, even if your title history doesn’t.

3. Use your skills in new ways, with others.

My friend Shannon used to run retreats while working her corporate job. It started as a passion project exploring how people build community and solve complex business challenges. That experiment turned into her full-time venture. Her corporate background was the springboard but the side bet was the dot.

Action: Collaborate. Build. Volunteer. Put your skills to work in a new way that combines with your passions.

##Going forward. We can't predict exactly how our careers will unfold, or which dots will connect, but we can take action that creates more dots. Some will fade. Some will connect. The goal is to trust that the act is worth doing.

So our future self will be thankful for the courage we had today.