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Some of the best decisions that I have made in my career looked, on paper, like mistakes.
For example, after my first daughter was born, I took more than a year out of the workforce, my first real break since I started working as a teenager. Later, I left a good, stable job in recruitment, where I was flourishing, for a lateral move with no pay rise and responsibilities that had me starting ‘at the bottom.’
On a progression chart, those choices read as breaks or setbacks, but they are a big part of the reason why I can do my job now.
I say this not because my path is wildly unusual, but the opposite: because it is surprisingly ordinary. Careers of today don’t follow the same linear path as they might have 20 or 30 years ago. They pause, sometimes on purpose, and it's more common than not to see sideways or even slightly backward moves before an upward trajectory.
The systems that decide who gets more opportunities still assume that someone will climb steadily and not stop. It’s no longer a realistic expectation, nor is it always desirable, and building an organization around that assumption costs more than leaders admit. And the unfortunate fact is that it is more frequently women who pay the price.
Careers of today don’t follow the same linear path as they might have 20 or 30 years ago. They pause, sometimes on purpose, and it's more common than not to see sideways or even slightly backward moves before an upward trajectory
The problem with the ‘perfect’ career path
The distinct challenges that women face at work are often assumed to manifest overtly: being talked over in meetings, misinformed assumptions around technical capabilities, and being cast as a villain for asserting themselves. These issues do still exist, but the more stubborn, lasting problem is structural. Promotion cycles and performance ratings assume a life that runs in a straight line. Anyone whose life doesn't, which is most parents and a disproportionate number of women, gets measured against an unrealistic standard for the modern day.
This is not a plea for a lower bar. And to be clear, the fix is not an exception bolted onto a system that stays rigid underneath. It should be admitting the system is misinformed. A career with a lateral or even backward move, or a few years spent going deep rather than up, or a legitimate pause, is not a broken version of a good one. Over careers spanning forty-plus working years, it is actually a very normal one.
The most ambitious thing you can do over that span of time is keep going. The people still doing their best work three decades in are not usually the ones who started fastest out of the gate. They are the ones who knew when to move laterally to take on something new that they may not be as good at yet, and when to ease off before the work burned them out. But none of that counts as ambition in a system built to reward speed.
When frameworks become fences
I was an early hire at Signifyd and have had the privilege of helping it grow from a startup into a global company.
Early on, careers went wherever the business needed them. Someone spotted a gap, enthusiastically stepped into it, and a few months later was doing a job that hadn't existed when they joined.
This is a common phenomenon in startups and scaleups. What I’ve also observed beyond Signifyd is that, with scale, structure stops being optional. Employees rightly want to see how to progress, so organizations build frameworks which are useful - until they harden. The risk is that frameworks are built rigidly with one biography in mind: joined junior, made manager, kept rising in the same function on schedule. But many of the best leaders I know look nothing like that. They moved between teams or built expertise in areas of the business that they had no background in. As a company grows, the job is to intentionally protect that kind of growth because otherwise, the system will squeeze it out.
Careers should fit around life, not the other way around
Having a child fundamentally changed how I work. When your day has to end at a fixed time because someone needs to be collected, you become far more deliberate about where your attention goes. It teaches you the difference between activity and impact.
Delivering Consistent HR Services for Deskless Workers
That made me a better leader than any period of late nights and early mornings ever did. I became less interested in who appeared busiest and more interested in what people actually delivered. The real test of a team isn't how much motion there is, but whether the way people work delivers impact at a sustainable and scalable pace. And the best leaders know how to tell the difference.
It is also why I prioritise true flexibility. Often, we think of flexibility as agreeing to one-off accommodations; an employee might request two days working from home, it gets approved, and the conversation ends. But in reality, people's circumstances are constantly evolving. What works when you have a newborn may be completely different once that child starts school, or when ageing parents begin to need support.
Flexibility that can’t evolve is not real flexibility. True flexibility has to be an ongoing dialogue and requires managers and employees to consistently be open to revisiting what is working, what is not, and how individual needs have changed over time.
That principle extends well beyond flexible working arrangements. Organizations assume that once someone reaches a certain level of seniority, the need for support or understanding somehow disappears. In reality, though, senior leaders carry the same pressures as everyone else, if not greater. They are just less likely to admit it, and desperately need managers and boards who understand that their value should not be linked to being reachable at all hours. And they set the tone whether they mean to or not. HR teams can write the most enlightened policy, but if every executive takes the same narrow route up, people interpret the route, not the policy.
True flexibility has to be an ongoing dialogue and requires managers and employees to consistently be open to revisiting what is working, what is not, and how individual needs have changed over time
Retention is not a scheme you launch when someone is already interviewing elsewhere. It is the sum of whether people felt understood while they worked for you. It comes from promotion systems that value contribution over time served. It comes from flexibility treated as the baseline, not a perk, and from leaders who plainly got there by more than one route.
None of this is about tolerating the non-linear career as a concession. It is about accepting that the career that bends and doubles back is a normal one, and actually building for it. Companies that do will keep and attract the best people.
Emily Mikailli serves as Chief People Officer and Chief of Staff to the CEO at Signifyd, where she leads global people strategy for the world's leading commerce protection platform. Since joining the company in 2016 , Emily has been instrumental in scaling Signifyd into to a global organization with offices across San Jose, London, Belfast, and New York.
