2019, what doesn’t kill you…

Benji Portwin
6 min readJan 4, 2020

Careers are all about experiences, there is no winning or losing, it’s just about creating great memories… I took my L(oss) and I bounced back, life is a rollercoaster.”

Anthony Joshua, 2019, shortly after defeating Andy Ruiz in their second bout

2019 was a year of “firsts” and probably the hardest personal and professional year of my life. It was the first time I truly tasted failure, the first time I had major surgery and the first time I lived alone. Because of this, it’s a year in which I’ve learnt an awful lot about myself and what I can (and can’t) handle; so much so that when reflecting upon the year I started crying. Some part of this was due to relief, but a large part was also pride for coping with the ups and downs of what was a frenetic and emotional experience.

Along the way I learnt some lessons, which I thought I would share in case they are of any use to others:

What doesn’t kill you (might) make you stronger

Despite having a really great start to the year, I was part of a failed product in Q3 and the experience broke me for a while. The shock I felt after being taken off the product was only comparable to that I’ve felt when being mugged for my phone. I thought my world was falling in, but it didn’t; I coped and although I wouldn’t wish the experience on anyone, I believe I am now twice as resilient as I was before — it’s not so easy to knock someone down with the same punch twice. Two things made sure it wasn’t a knockout, a therapist and really good friends. Do everything possible to try and get both. When I was recovering from the knockdown, with my confidence in tatters, I had to remember what I had always coached others: “Back yourself”.

Be there for those in need

I’ve often heard boxers talk about how their “friends” deserted them when they lost the big fight and looking back it was interesting to see who was there for me. The people who sent me a private message asking if I was okay, the people who went out of their way to give me a hug — and those that disappeared. When something bad happens to someone else at work overcome your fears, the potential risk and awkwardness; overcome everything, because they need you and they likely don’t even know it enough to ask. Every check-in, every offer of lunch, every GIF, will make a difference.

If it has to be now, it has to be no

I remember hearing a phrase from an entrepreneur a while ago “If it has to be now, it has to be no”. It was all about how she ran her business when someone tried to pressure her into doing something quickly. Despite knowing (and quoting) this phrase often, this year I forgot it. I was persuaded to take a challenge I shouldn’t have and then when shit got really crazy, I was unable to take a step back and say no. For those that know me well, this may come a shock. I’m normally confident about when to trust my gut and push back, irrelevant of seniority; but 2019 reminded me were all susceptible to the same traps, even when we know they exist.

You always need to earn the right to be listened too

I’ve been working “properly” for over 10 years now and if there was one thing I told myself as I grew up, it was that I should never say “you’ll understand when you’re older”. Call me a millennial, but my internal (and sometimes external) response to this statement has always been “Go fuck yourself”. So when I clashed in my first week with my 21 year old tech lead, about how we were going to work as a team, it took everything I had not to say “I just know more than you”. But I didn’t. Instead I explained things from first principles and openly admitted that he may know more than me. It was 10x harder than saying “I’ve just had more years of work than you”, or even “my experience has shown me”, both of which are proxies for ageism. The conversation therefore 10x more effective for that reason. Not only did we form a fantastic working relationship, he taught me a hell of a lot and became close friends; none of which would have happened if I’d mentioned “experience”.

Work less, travel more

My partner and I agreed to take two bigs trips a year (when money allowed) and this year we took none. This year I prioritised work and was unlucky enough to need hip surgery. The latter can’t be helped, but the former can. I worked longer hours this year than any time in my life, including when I was a consultant. I worked late, came in early and worked half my weekends. Now the end of the year has come around I’m filled with regret about a year lost.

Trust by default, but know the game

Trusting by default has its risks. It allows me to build relationships quickly and make friends within a single conversation. However it also has its risks and this year I saw more of the negative side than I had done in a while Firstly the positives, I took my “friend dating” skills from NYC back to London and made a whole bunch of new friends, bringing me joy and satisfaction, especially considering how hard it can be to do this in your 30s. I also made friends quickly at work, something I’ve done in all my roles, but was much harder being older than most of my colleagues. Sadly however, I also put my trust in some people who then let me down. I was only the prettiest girl at the dance, as my friend Michelle used to say, and once the music stopped, so did our friendship. It hurt and made me question my trusting by default policy, but luckily there were enough wins not to change it.

Building great teams still makes me incredibly happy

I had the pleasure to build another amazing team in the first half of this year. We formed quickly and spent 6 months together, building a couple of great products along the way. It was kind of team that runs itself and where everyone felt like they belong. The kind of team who go to someone’s house on the other side of town when one of them leaves the company. The kind of team that even once disbanded, meets up for a Fika and makes you smile. Always prioritize building teams, no matter what anyone says, they are the people you will remember in life.

Fuck it

I had hip surgery this year and it terrified me. I’ve played sport at least twice a week for 20 years and the questions I had dominated my thinking night and day. Would I play sports again? Would there be complications? Should I just put up with the pain? I had it, it wasn’t that bad, despite them leaving some metal in me by accident, and at the end of the day you sometimes you just need to shout fuck it and get on with life. Oh and music still helps everything, it’s power never ceases to amaze me.

Every length is a victory

A couple of years ago in a New York YMCA frequented mostly by older people, I got out of the pool looking visibly annoyed, having only made 18 of my planned 20 lengths. As I stared at the clock, an older gent asked me “Hey, what’s up kid?” in a thick New York accent. When I explained my situation he said “Ha! Every length is a victory. ‘’ It made me smile and almost instantly feel a little better, sticking with me ever since. When you hold yourself to the highest account at work, with your friends, in your relationships, in everything you do; it’s easy to forget that doing something 90% is actually pretty fucking good. Celebrate what you have done, don’t always think about the lengths you didn’t make. Go a bit easier on yourself in 2020 :)

I hope you’ve found my learnings useful. I’ve tried in recent years to prioritise honesty of my experiences over fear of reprisal; so if you’re reading this and disagree, that’s ok. Not everyone’s value systems will line up with mine and that’s ok, I bear no hard feelings :)

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Benji Portwin

Head of Digital, Product and Design @NewLook. Previously @accurx, @HawkfishNYC, @Monzo, @Spotify, @NHSDigital, @GDSteam