Careers & Startups: Moving past the ladder metaphor

ashwini asokan
3 min readNov 19, 2019


I spend close to 70% of my time hiring these days. When a startup is in growth mode, most of the team has moved from the early adrenalin and excitement to getting repeatable, scalable processes in place, in pursuit of sustainable, forecastable growth. Topics on the aisle way move from all things product to all things customer and team. It’s a significant shift you can’t miss.

As new faces, senior roles start to fill in, and you cross that Dunbar number — employees start thinking about career plan, path ahead, organizational change. Change is hard. But change that comes from org growth is particularly hard on early teams that spend an exorbitant amount of time with the founders or the leadership teams.

We often talk about change management when it comes to customers, rarely do we address the same with our own organizations. Here are 5 things I discussed with the team about how to think about career management in a startup.

  1. Some of the best careers are rarely linear or straight lines.
    They look like the image above, rather than a ladder or a set of steps to 1 place — A career looks very different when you’ve had a chance to pick a variety of skills along the way, experiment, jump at opportunities, earn the right to respect and grow more holistically.
  2. You career is not about climbing a ladder, it’s parkour on rooftops. It’s weird we talk about ladders when we talk about careers. We imagine vertical growth more than anything else. In reality, some of the most important people in a company, have no fancy titles, jump into every oppty they see in front of them, step up when no one else does. They are understudies for long periods of time that eventually become the centers of power because they make themselves so essential to so many functions, you can’t image an org without them. They don’t climb a ladder, they parkour on rooftops and leap from strength to strength, growing skills and going places most others in the company don’t.
  3. Early startups need generalists, no better place to create a rocketship of a career. Especially in early stage startups, roles are generalist focused, what is often known as T-shaped skillset — so jump and take every opportunity you get to do what the company needs at any given point in time. Existential questions about life, can wait. Pick up a variety of skills, learn to play strategy games, learn what it means to deal with people, before you let existential questions about career paths freeze you out of the world of possibilities before you.
  4. You own your career — My mentor @feraldata would always say — YOU OWN YOUR CAREER. The best mentors open doors to places you never knew existed, to challenges you didn’t know you could take on, to lessons no one told you — you’d learn. No one ever gives the top people in a startup their positions, they make their own positions, create paths that never existed before them.
  5. Take people along for the ride — Pick the people you surround yourself with. Pick the people you will take with you along for this ride. Pick the people you’re going to make successful during this ride. It matters. Make others successful and watch your own career soar.

Thinking back about my own career, I can say this for sure — breaking down the metaphor of a ladder, allowed me to create spaces where I could bring my own strengths to create my own landing space. More often than not, this was not the top. And this ‘other space’ I designed over and over again, often made what others defined as ‘the top’ — entirely irrelevant. The top is an illusion. It’s not a single place that we’re all running towards. To realize that you can absolutely create a new place of power, a new game, create your own rules and bring like-minded people into that game, can be the difference between following a rat race of a career, and pursuing a meaningful career growth. Think about your own career inside a company your work at, as simply a canvas, to allow you to paint whatever picture you want.

Disrupt the top. Break the ladder. Make a new career. A non-linear one.



ashwini asokan

Founder CEO Mad Street Den, an AI and Automation startup. Musings on life, growth, AI, SaaS, Startups, Design.