Plain Sailing or a Rollercoaster Ride — What does the job market want?

Edward Woolley
6 min readFeb 3, 2021

What appeals to you more: calm clear open waters and a safe journey to your destination; or a more thrilling ride with lots of twists and turns?

And more importantly, what sort of a person are YOU in this respect? Are you more slow & steady or do you go thru many highs & lows? Perhaps you’re a mixture.

Anyway, why care to ask? well if you realize that both can be a strength, and both can be regarded as desirable when you head to that next job interview, then you know how to put your best foot forward.

But anyway, we need some data to explore and better understand. I’ve put the question to the Creative Product Managers and my contacts who have all been a tremendous help — thank you.


Imagine you are currently hiring, and you have the choice between two candidates. Both of them, have a history of hitting targets and meeting business objectives. However, there is a clear difference ……..

The first is more “smooth sailing” — a slow & steady type

The second has been thru many more ups & downs

Remember they both deliver. Whom would you pick?

There is no right or wrong answer, and as such, the question created some great engagement and a lively debate. People were split down the middle. Having said that, there are nevertheless some conclusions that can be drawn (explored below) that’ll help you on your journey!

Exploring The Results

The general consensus in favor of the second — the rollercoaster ride — was as follows:

  • Mistakes or failures are valuable provided you learn from them and do not make them again. In doing so, you effectively stress-test your’s, the team’s, and the product’s capabilities, which provide valuable lessons (that most likely wouldn’t have been uncovered otherwise) to preempt such problems moving forward — which can be really valuable to an employee. Tho you can learn thru successes too, for a lot of us there really is no better way than learning from your mistakes. Because our mistakes have the power to humble us, keeping our egos in check so we are more open to feedback & criticism from others, as part of an open collaborative, and productive team built on trust. There’s no room for ego in highly functioning collaborative teams.
  • What’s more, if you can prevail & succeed thru challenges and get back-up after knock-backs you build a strong sense of character — aka resilience, which is needed in the VUCA (Volatility, uncertainty, complexity and ambiguity) world we inhabit.

It’s paradoxical to think that slipping up even if rectified, would be seen more favorably than someone who delivers results without any bumps in the road, but that is exactly what the recovery paradox suggests:

The service recovery paradox (SRP) is a situation in which a customer thinks more highly of a company after the company has corrected a problem with their service, compared to how they would regard the company if non-faulty service had been provided

Service recovery paradox — wikipedia

Okay SRP is a different context to employment and the jobs market; however, resilience is becoming a much sought-after skill among recruiters, and here’s what Sam Lessin — who was Facebook’s VP of Product Management — had to say :

SL: I look for resilience — because if you are doing something hard, there will always be failures — a ton of resilience. People who have overcome adversity in their life…………… The perfect A student at the best school who has cruised through has more emotional learning to do, and more to prove about their ability to pick themselves back up after defeat. I like forward trajectory, even in a resume that is spotty. My resume is not like that, so I look for it in others. I had to overcome reading issues when I was a kid, which was pretty informative for me.

Product Management Stories: Sam Lessin — kleinerperkins

Reassuring for those of us who have been thru some tough times in our lives, but within the context of our professions and careers, I’m sure such challenges — even if they were overcome — could ring alarm bells for some hiring managers. Especially if they were severe, for instance: revenue and reputation loss or even bringing the product and business to near failure.

My contacts who own businesses, tell me no matter how impressive the revival or comeback they’d rather just pick the “safe bet”. They admire the tenacity but their all-important bottom line is what matters.

But in some circumstances, for example in a crisis where the business is constantly “putting out fires” a candidate who’s been exposed to such conditions before would be more appropriate — as crazy as it sounds. Fight fire with fire!

And what about if your working in the R&D space or even the charity sector, where projects are financed differently. R&D money is often set aside for ambitious experiments, so an individual who takes risks and can drive such feats may be more favored. And in the charity sector, the same can apply. Funders are often more incentivized to fund big show-stopping initiatives rather than all-important business as usual.

Therein you must consider the disposition, culture, and sensibility of the prospective company where your applying. For instance, when I lived in canary wharf a friend of mine was applying to work at the investment banks, where there is quite a different risk culture between them, so this was taken into consideration when he applied.

For the more conservative of the firms, he didn’t highlight his ups & downs so much, but his resilience nevertheless came thru — from the strength of character he’d built up over the years taking risk after risk.

Then for the firms where risk is more encouraged, he divulged more of that — which let’s not forget can make for compelling storytelling! A good narrative always has twists & turns, ups & downs and storytelling is a powerful emotive force used in business to capture the hearts of imaginations just like anywhere else. And selling yourself is no different!

So ultimately what I’m saying is be yourself, but when you presenting yourself to an employer, craft a narrative based upon yourself that is attractive to them.


You’ve probably realized from the beginning there is no right or wrong answer to my hypothetical question, as there are no absolutes.

However, hopefully, it’s nevertheless been a worthwhile thought experiment in considering both extremes:

a smooth sailing steady type of person OR a rollercoaster ride in a VUCA world.

I personally am no longer as concerned about my low points, as for the right audience, they can be framed as strengths when they appreciate the revival, showing my determination and ability to turn things around.

And for those of you who go from strength to strength, without any real low points, you needn’t be concerned that you need to present yourself as having recovered from many insurmountable feats to make your personal story more compelling because there’s an audience who finds a more the steady plain sailing journey to success reassuring.

Success is what matters. How you get there depends on you and the preferences of who you surround yourself with, including where you work.

Be yourself. Focus on your strengths and best present them to your audience for maximum impact.

Ultimately you have to get the right balance of risk for your character.

I’m not advocating looking for risks to learn from them — that would be stupid, creating unnecessary problems — but challenges naturally arise from pushing oneself and as part of a team towards a common goal, where risk is an inevitability.

Originally published at