5 Insanely Successful Women Reveal What They Wish They’d Known at the Start of Their Careers

Career Lessons Successful Women

Remember that moment in the Sex and the City movie where Carrie Bradshaw turns to her assistant and says, “Enjoy yourself. That’s what your 20s are for. Your 30s are to learn the lessons. Your 40s are to pay for the drinks.” Well, I would also add that your 20s are for making a copious amount of career mistakes.

The words “I have absolutely no idea what I’m doing” have been ringing in my head throughout the majority of my 20s. And it all goes back to what Hannah Gale said in her #My9to5 interview: “Most people have no idea what they’re doing – they’re just fumbling along and praying no-one finds out that they’re secretly a fraud.”

I often feel like I’m not making enough progress when it comes to my career. However, I try to view every mistake and missed-opportunity as a lesson. And I always find solace in other women’s career stories. (Honestly, talking to women about their work and ambitions is one of my favourite things to do in the entire world!)

This month I have invited five ridiculously inspiring and accomplished women to reveal the one thing they wish they had known at the start of their career. Think of this as validation that everyone – no matter how successful – has had important lessons to learn along the way…


Blythe Harris Stella & Dot

“Having a point of view is more important than knowing all the answers.”

“Having confidence and a point of view is more important than knowing all the answers. If you have strong instincts and an appetite for active listening you will always come to the right conclusion. Do what you love and love what you do. People who are happy are more than 30% more effective at what they do. So don’t force yourself into a career you are not passionate about. And remember to cultivate both curiosity and risk taking in yourself and your team. It’s critical to fail fast and learn early on in your career.” – Blythe Harris, Co-Creator and Chief Creative Officer, Stella & Dot and Co-founder KEEP Collective


Liz Earle MBE Career Advice

“Customers love to connect with actual founders and not just faceless brands”

“I wish I’d been braver in building up my own social media earlier, as customers love to connect with actual founders and not just faceless brands. I was always nervous about putting myself in the spotlight but I now really love having my own voice on Instagram especially” – Liz Earle MBE, a wellbeing entrepreneur and founder of Liz Earle Wellbeing


Jennifer Dickinson The Edit

“Follow your dream, but don’t be afraid to find a new one, too.”

“I’m more emotional than logical, and that has minimised any career regrets because I haven’t often gone against what my gut is telling me. But with that double edged sword of hindsight, I wish I had kept my career options open more. In my early twenties, I imagined that for those of us lucky enough to have a passion, there was one route and you followed it as far and as fast as you could. I was pretty good at that, but now I believe we all have a few careers within us. You can start out in one, do well, and still get to a point where you feel unfulfilled or maxed out. I was unsure about leaving traditional publishing (I worked at ELLE and Harpers Bazaar) to come to Net-A-Porter. But the learning experience has been second to none. And I don’t think I’m done in my ‘careers’ yet. Follow your dream, but don’t be afraid to find a new one, too.” – Jennifer Dickinson, Editor of The EDIT magazine at Net-A-Porter


Monica Vinader Career Advice

“Often when a company grows fast people are left out of the loop.”

“One thing I wish I’d understood from the start is​ the importance of maintaining effective internal communication. It is so important to make sure that as a company grows the entire team maintains visibility of what the business is doing and why, so that they feel involved and can deliver towards the overall goals. Often when a company grows fast, it’s easy to forget this and people are left out of the loop.” – Monica Vinader, Founder and CEO of Monica Vinader


Holly Tucker MBE Career Advice

“Trust your gut instinct, it’s your internal compass, your true north.”

“Having built notonthehighstreet.com, and now starting up Holly & Co, there are many lessons that I’ve learnt along the way. But one stands out above all the rest… Trust your gut instinct, it’s your internal compass, your true north. You will have many people around you along the way who will advise you – often you will have hired them on the basis that they know more about a certain subject than you. But if you can stay in tune with your own instincts and be guided by them, you will always be on the right path. Even if others challenge you or disagree with you, don’t ignore the voice that was built inside of you!” – Holly Tucker MBE, Co-Founder of notonthehighstreet and Founder of Holly & Co


What’s the one thing you wish you had known at the start of your career? Leave a comment below to have your say…

P.S. 5 fashion insiders share their top tips for networking


  1. I’d say: It’s OK to change your mind is a pretty good one. Sometimes we get so attached to some old dreams iof ours that it almost feels like a betrayal to leave them behind, just as Jennifer said!

    • cocos_tea_party says:

      YES! Agree with this 1000%! It’s so true, but it can be really hard to say goodbye to a dream and move onto something else. xx

  2. Chloé Adelia Watts says:

    I love this post Ella, some amazing points that I always want to be mindful of x

  3. These are so interesting and I’m so pleased with what Jennifer said, as lately I have been thinking more about adding other careers or side hustles to my portfolio! Steph x

  4. Jennifer Dickinson says:

    Hey Ella, I wonder whether you could do a post on how to find the courage to/get started on a whole new career? Seems as though a few of us are open to inspiration!

  5. cocos_tea_party says:

    Thanks Molly! So pleased you found it inspiring.


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