“You can only connect the dots looking backward.”
We’ve all heard that Steve Jobs quote a million times. But it hits very differently depending on where you’re standing in your life.
Looking at my own career so far (moving from management consulting to early-stage startups, then into big tech sales, and now running Neverdrift), none of those moves felt like they were neatly leading anywhere.
At the time, they were just the next chapter, informed with as much intention as I can. I definitely didn’t have a grand master plan.
It’s only now, as I build Neverdrift and coach others, that I can turn around and actually see the connections.
The Toolkit You Didn’t Know You Were Building
When you’re in the thick of a career shift, it’s hard to see how your past life translates to your next one.
But every chapter leaves behind a set of tools you don’t realize you’re accumulating until you suddenly need them:
- Consulting taught me how to diagnose. When you get dropped into a new case, you don’t know the answer right away. You have to figure out what the actual problem is. It taught me to ask better questions, break down complexity, and separate symptoms from root causes. I use this constantly in coaching—because usually, what someone thinks is the problem isn’t actually the problem.
- Startups taught me how to build. There were no neat job descriptions. You wore every hat, figured things out as you went, and learned how a business actually fits together. That scrappy resourcefulness is the only reason I survived becoming a solo founder.
- Big Tech taught me structure and scale. Working in a large organization showed me what great processes and systems look like when you’re operating at scale. And my time in sales and account management pounded home a key truth: having a good process isn’t enough. You need metrics, targets, and actual outcomes.
Learning How People Think
Maybe the most valuable part of all these jumps was getting to work alongside wildly different, high-functioning people – consultants, founders, engineers, salespeople, marketers, and corporate leaders.
I got a front-row seat to how differently capable people think, communicate, make decisions, and deal with pressure.
That exposure changed everything for how I coach today.
When I sit down with someone, I’m constantly trying to understand the exact lens they operate through: What drives them? What do they default to under stress? What assumptions are shaping their choices? What works for them and what doesn’t?
Years of working alongside distinct personalities gave me a much richer map of those different human operating systems.
You Don’t Need the Whole Path Figured Out
Today, all these random pieces finally live under one roof at Neverdrift:
- The curiosity and diagnostic thinking of a consultant
- The resourcefulness of a startup operator
- The appreciation for systems from big tech
- The outcome focus of account management
I couldn’t have designed a career path backward to prepare for this any better. But the wild part is: I didn’t know any of this while I was living it.
And I think that’s the real lesson here. You don’t always know what the dots are for when you’re making them. You just keep learning, meeting people, trying things, and getting your hands dirty.
You don’t need to have the whole path mapped out right now. You just need to keep intentionally moving, paying attention, and collecting the dots.
Because eventually, you’ll turn around, look backward, and say: Oh. That’s why I needed that.
If something in this post made you pause, that’s usually worth looking at. Learn more about working with Natalie here.
