Jess Reviews: Anna Wintour’s Address at the Oxford Union

I recently got into watching addresses from successful and famous people at the Oxford Union, because I don’t have the time (or money) to see them live (see my post about What They Don’t Tell You About Oxford). One particularly interesting talk I listened to was given by the editor-in-chief of Vogue and general fashion icon, Anna Wintour. She had some very interesting advice for careers, which I wanted to give my thoughts on.

For those of you who are interested, here is her full address.

For those of you who cba to watch this, here is a quick summary:

Anna Wintour explains her career path, starting from when she left school at 16 to go straight to work. She starts by saying something that contradicts most of British schooling and thought: “Don’t over-specialise. Be intellectually free. Try lots and lots of different things.”

She continues on this train of thought to encourage us to explore different things, stay intellectually curious, and develop many different skill sets. Anna explains that she finds people who are too specialised quite frustrating, as it’s difficult to talk to them.

This is true of corporations as well – sometimes they can get stuck in their ways, with the mindset that this is how they’ve done it for so long, so they resist change. It is important, especially at a young age, to “try, and possibly fail, at many different undertakings.” Embrace change, become self-sufficient, learn from others.

It is also important to not just live your life through social media. Even though it is a fantastic tool, and has democratised many industries including fashion and media, some people seem to have started to live their lives through their phones rather than experiencing life for themselves. As Anna says, “Fame doesn’t necessarily translate into success” – it is best to have some substance, talent or skill so that fame is well-deserved and longer-lasting.

Finally, Anna ends with recommendations to get outside of yourself and help others; this feeds back into your work. Live with intention and you’ll be able to produce excellence in every sense. Seize the opportunities that lie ahead of you.


Anna is a very eloquent, efficient person, and this really came across in the talk. She clearly knew her audience well from speaking at Oxford before, so her words were well-received.

She had clearly written this piece in a hurry – she wasn’t fluent or practiced at it, and looked like she was mostly reading off a script. However, I don’t blame her for that – she is a busy lady, and only the day before was flying over from Italy!

Anna’s efficient personality also really shone through in the Q&A after the talk – her short answers to some of the audience’s questions were exactly what is needed, even if it potentially made things a bit uncomfortable. Some questions weren’t the most intelligent (“What are you grateful for?” is the most generic and least relevant question, imho) and Anna answered them politely, truthfully, but concisely.

I have real admiration for this approach – it is effective, and she is certainly not like many other Union speakers who love the sound of their own voice and want to bask in the limelight for as long as possible. By speaking honestly and concisely, many more people got to ask questions.

Don’t Specialise Too Much

“Try, and possibly fail, at many different undertakings.” This message really stood out to me.

My parents, since a very young age, wanted me and my brother to choose something and specialise in it. The logic was clear: become an expert, be invaluable to a company, and you’ll have the power to push for fair wages and decent benefits, and your job will be stable.

However, this philosophy never really resonated with me. I’ve always been interested in learning new things, and becoming an expert in one field made me worry about becoming too insular and tied up.

I’ve always been one for learning new things, and I am usually suspicious of specialising (or maybe it’s my difficulty in making decisions)

Specialising so that we become difficult to replace in our jobs is certainly one way to freedom – it makes companies willing to pay us for our expertise, so we can negotiate better terms for ourselves. However, this can only really lead you to a middle-class or average life – to be truly extraordinary, like Anna, you have to know a bit of everything, so that you can see the wider connections and create something forward-thinking and different.

Be Multidisciplinary

Being multidisciplinary allows you to communicate with many different people; you can understand them and convey your ideas to them. It also allows you to draw connections between seemingly disparate ideas, and produce something new.

Having multiple interests and skill sets is becoming more important in an accelerating, ever-changing world – it gives you the flexibility to ‘pivot’, i.e. change directions. This is why “soft skills” like communication, team work and organisation are so important – they allow you to excel in whichever field you choose.

DofE is one of the ways that schools can teach teamwork and collaboration.

Understanding the nuts and bolts of the industry or business you’re in allows you to be self-sufficient. It makes you better at your job because you understand the fundamentals of what it is you’re doing.

Finally, being multi-disciplinary generally makes you more adaptable, less resistant to change. It is easy to get set in your ways, especially if you’ve worked in something for a long time, and this might blind you to other opportunities.

“Don’t close your mind to other callings.”

Anna Wintour, The Oxford Union

Be Intellectually Curious

Being intellectually curious ties in the idea of being a multidisciplinary polymath as well as the idea of learning from other people’s experience.

It is possible to take a quiet route to the top – you learn from others, better yourself, produce better work, and sometimes that get recognised by the right people. Experience and training are very important. Work with and learn from the best, but make sure you have the freedom to make mistakes and pivot. Be relevant, agile and educated.

Being intellectually curious also prevents stagnation – being open to new things and ways of working keeps you aware of change and can help you to assess if it’s right for you or not.

Be Self-sufficient

Becoming multidisciplinary helps you to become self-sufficient – this is especially true in the media industry, where everyone is their own writer, photographer, PR and sales.

Self-sufficiency helps you to make do with tiny budgets and tiny staffs, which brings creativity and freedom along with hustle and stress. In my experience, limitations produce truly creative results – I think that thrifted outfits are often much better thought-out and more satisfying than store-bought, everything-automatically-goes-together style!

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3 ways to style something out of your comfort zone 😕⬇️⁣ ⁣ There’s no better feeling than finding gems at the thrift store that look so fabulous we can’t help but to snatch it up. But once we get home, these gems end up sitting in our wardrobe. They are so different to the rest of our wardrobe that we can’t figure out how to style it!⁣ ⁣ I’ve been there before. I found this beautiful corduroy blazer on a £1 rack in a @barnados_uk store, and I just had to get it. I had no idea how to style it though, and it ended up sat in my wardrobe for a while. Here is how I managed to style it!⁣ ⁣ 1. Get googling! 💻 There’s no better place than the internet to find inspiration – simply Google “corduroy blazer outfits” (or insert your own gem here) and look on Google images. There should be something for everyone! Pinterest is also another site I love.⁣ ⁣ 2. Get creative 🖌 pick some other clothes in a similar colour or saturation, even if you think it might clash. Put the outfit on, and assess it in the mirror. You might be surprised at the new combinations you find!⁣ ⁣ 3. If all else fails, wear an all black base. This was definitely the first step for me to make this corduroy jacket more wearable for me!⁣ ⁣◽ ◽⁣ ◽⁣ ◽⁣ #secondhandfashion #secondhandstyle #secondhandclothes #chooseused #secondhandfirst #prelovedfashion #recycledclothes #thriftedthis #thriftedfinds #thriftstorefinds #thriftshopping #thriftedfashion #thriftedstyle #thriftedootd #kpopfashion #kpopstyle #kstyle #exostyle #xiumin #charityshop #buysecondhand #shopsecondhand #thriftcommunity #notbuyingnew

A post shared by Jess (@eco_kfashion) on


(Above is my new insta, where I use thrifted clothing to recreate Kpop idols’ outfits! Check it out if you like 🙂 )

Cultivate Your Point of View

It is important to develop your own point of view. I think too many people these days follow the crowd and don’t think for themselves; this is most notable in politics but is true in almost every field. Give this Wait but Why article about how to think for yourself a read – it was really enlightening for me, and I’m definitely trying to implement the strategies he outlines to become an original thinker and a real scientist!

Anna also tells us to “trust and cultivate your taste”. This is something I find quite difficult, because my love of learning has showed me how wrong I am about many things, which has led me to distrust myself and my opinions in most areas.

Photo by Rebecca Grant on Unsplash

Listening to and trusting my intuition is something that I need to learn how to do – it’s something I trained myself out of when playing chess, but I have recently started to realise how important it is, especially when it comes to people (playing any game that requires reading other people, like Poker or Deception; or even figuring out if someone is a true friend), my interests (whether that’s starting a new insta, writing a blog or even my options choices for university) and making decisions without knowing all the facts (like choosing a career).

Anna is so good at what she does because she reacts intuitively to collections and designs, and because she has good taste (whatever that means) and an eye on the pulse, she is able to make the future into the present to stay current.

Social Media

Social media is a fantastic tool, and must be treated as such. Everyone has a voice, simply by the way we live and the choices we make. People want to know how you work, what you like, how you think – and social media is the place to go if you want to know what’s current and trending.

However, it’s also important to have real-life conversation, to truly look at things, experience moments, and not let social media substitute for your life.

Photo by ROBIN WORRALL on Unsplash

As Anna says, “Fame doesn’t necessarily translate into success.” With social media, it’s easy for just anybody to rocket to fame, often with no real substance. Fame is fickle: once it’s gone, you could be left with nothing.

Have Substance

If you have real substance – a talent, skill or set of skills – you don’t need fame to be successful. This is the reason why I love learning – it’s important for me to build myself up so that I can give back more effectively to others and help better society.

In a way, this section contradicts slightly with not specialising too much – to have substance, you must be able to bring real value to the world. To bring value, you must be able to help others, or be really good at something, or bring a unique perspective.

As Anna said, “The more you do, the more you can do.” By becoming good at what you do, you meet people and gain leverage to help others, as well as gaining opportunities in other areas.

Helping others is also deeply fulfilling in its own right – there are so many problems with the world that you can absolutely pick one and get started! You can also choose to solve more than just one problem, and when you make solving a problem the end goal, you have to stay flexible to keep up when anything changes.


So after this very long (1900 words!) post, what can we take away from Anna Wintour’s talk?

  • Explore your interests
  • Don’t be afraid to fail
  • Understand the nuts and bolts of your business
  • Be multidisciplinary
  • Strive for substance, not fame
  • Cultivate your point of view
  • Live with intention
  • Seize opportunities

I think Anna Wintour is a very admirable person – she is understatedly confident, powerful, multi-talented and forward-thinking. There are so many things we can learn from her against-the-grain career path!


What do you think of Anna Wintour? Do you agree with what she says? Let me know in the comments!


5 thoughts on “Jess Reviews: Anna Wintour’s Address at the Oxford Union

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