Sarah Helppi On How We Need To Redefine Success



Have you ever noticed how often we equate success with more? Whether that’s more products, more profits, more activities or more accomplishments, we buy into the belief that we have to do more to have more to be more. And that will sum up to success. And then along comes The Great Resignation. Where employees are signaling that the “more” that’s being offered — even more pay, more perks, and more PTO — isn’t summing up to success for them. We visited with leaders who are redefining what success means now. Their answers might surprise you.

As a part of this series I had the distinct pleasure of interviewing Sarah Helppi.

Sarah is the Founder & CEO of pre-loved luxury fashion search engine The 2nd Circle (www.the2ndcircle.com), alongside being a single Mum to a 7 year old daughter. For 17 years she helped grow companies like eBay, Expedia, lululemon athletica and Hewlett-Packard in marketing, finance and supply chain roles. Not to be considered all work and no play, she has been DJing since she was 23 and has a monthly radio show on Point Blank, the UK’s longest running house music radio station. She lives in London, UK but was born and raised in Canada.


Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

I’ve always been very independent. My parents split up when I was 5 and my mum didn’t earn a huge amount in her secretarial work, so we moved in with my grandparents for several years. I have a lot of fond memories of this period and I never went without, but my mum moving back in with her parents in her 30’s with a young child left an impression on me. This probably steered me down a business related career path — I saw what my Mum went through and knew I wanted to be financially independent. I thought being in business was the best way of achieving that.

Five years ago I went through my own divorce, but had no parents nearby to move in with. It also turned out that despite having a “business career” I was still not earning enough to support myself and my daughter. I put my head down on my work, moving jobs several times to accelerate my earnings. One role had a particularly difficult commute which was exhausting alongside being a single parent to a toddler. It got easier and I now look back on that period with pride — it gave me confidence that I’m stronger and more resilient than I had given myself credit for.

We all have myths and misconceptions about success. What are some myths or misconceptions that you used to believe?

I used to assume if you were well off, you didn’t have the same kind of health, relationship, family or career troubles. Money probably just made all of that easier and therefore all areas of your life were probably a success. I also used to think if you were attractive your life was probably much easier too! Yes, not worrying about money or your looks can be a blessing, if that’s your circumstance. It’s really been through the power of story telling in the media that has exposed the common experience of us all. Of course, However, the pandemic illustrated this for us too.

How has your definition of success changed?

I turned 40 in the pandemic, so I was ripe for cutting up my own rule book! Success comes when I am doing the inner work to figure out my real needs and wants and then taking actions to have those needs met. This extends across my career, health and relationships. Sometimes those actions are difficult or scary. They’re often full of unknowns. If I have that clarity of mind though, I know deep down I can’t settle for anything less.

This shift in how I view success came from several periods of extended sobriety in the last five years. I know when I drink at all, I’m blocking that inner clarity and probably short changing myself. Sobriety is a big part of my personal success now.

The pandemic, in many ways, was a time of collective self-reflection. What changes do you believe we need to make as a society to access success post pandemic?

We need a society that rewards more collaboration and kindness, rather than measuring binary outcomes like winning or losing, gaining or shrinking. But how? First — we need more feminine leadership. Not necessarily women, though that helps, but leaders of every gender broadening the way that they behave, communicate and incentivize the people around them. We need leaders with a broader sense of responsibility. An example of this might be more collaborating with competitors to share technologies and solutions that help reduce environmental impact. The traditional way of doing business is every company (or country) for themselves, but that’s very inefficient for society as a whole.

The way businesses are measured on success needs a complete rethink. Currently the performance of a company is determined by financial and profit measures. There is a small group of companies that are orienting themselves around people, planet and profit measures — a balanced scorecard. We need so much more of this. We need leaders to put their voice behind this and drive change with their boards and their investors, and then within their organizations. I have no doubt it will become a winning formula for business in the long run, as these organizations will be better able to attract talent and customers. Stick to the old way of doing things and you will be left behind.

At an individual and household level, we have to give up our conveniences. Our day to day lives are built on unsustainable practices. More government regulation and commitments are needed to drive this change, as uncomfortable as it may be.

What do you see as the unexpected positives in the pandemic? We would love to hear a few of your stories or examples.

I had an unexpected career change born out of a necessity to quit drinking!

Like many people, I spent the early days of lockdown eating and drinking a lot, but this quickly became problematic. In April 2020, I went completely alcohol free and stayed that way for over a year. The physical and mental health benefits were enormous.

I have had other periods of extended sobriety before, but this time it had a different tone. I began really questioning what I was doing with my life as my job had become extremely demanding and unfulfilling. Ending the day with a cup of tea rather than a glass or five of wine left me a lot of time to feel unsettled, but I was unable to pinpoint what I should do about it. As the sole earner in my household I couldn’t just up and leave, what else would I do anyways? And wasn’t the job market pretty difficult with so many companies laying people off?

I began free-form journaling, which is where you simply sit down and write 1–2 pages of whatever comes to mind. Three days later, I was reading a report for work and I had an ah-ha moment for a new business. I had never experienced such a “lightbulb moment” before, but what was I going to do with it?

A little while later, my corporate job ended when my role was made redundant. Having given so much to the company during my time there, it was tough to swallow, but soon felt serendipitous as I knew what I wanted to do next. I am now working on my business, The 2nd Circle, full time. I have brought on a co-founder and we will raise some funding next year to continue growing. Every day is a terrifying challenge, and being a single parent my financial anxiety is omnipresent. However I am learning more than I ever thought possible and feel like I am building something of value to the world around me every day.

We’re all looking for answers about how to be successful now. Could you please share “5 Ways To Redefine Success Now?” (Please share a story or example for each.)

The only way to truly redefine success in a way that is unique and authentic to you is to spend some time with yourself! How?

  • Journal. I won’t tell you to meditate — I can’t do it either — but writing stuff down in an unstructured way is an easy way to clear out blockages in your mind. You’ll begin to process as things go down on paper and clear space for new thoughts — like I with my new business idea.
  • Take social media breaks — a length that feels uncomfortable. No one will miss you. Which begs the question why you’re spending so much time on there at all. Be careful of the advice to “curate your social feed with people who inspire you” — just because you aren’t wasting time commenting on memes or your mate’s new puppy doesn’t mean the content is doing you any good. You “taking inspiration” from a tightly curated social feed can turn into you feeling like you need to be and do more very easily.
  • Think about where, when and with whom you’ve felt energy. When I first thought of my business idea, I started naturally waking up at 5am to research it. I was absolutely exhausted from my real job, but my start up idea gave me a fire I couldn’t ignore. I can still remember that period now. Have you had that experience?
  • Talk to one person. When you start getting some direction for how you’re going to redefine success, find someone to tell it to. Not for their opinion, but to put it out into the world. Does it feel good? Talking about things makes them a lot more real than when they just live in your head. Could you see yourself living this every day?
  • Read some powerful books. Take some clues for how other people figured this conundrum out. I recommend Glennon Doyle’s “Untamed” and Kate Northrup “Do Less”. I’ve read Untamed twice — if it landed with Adele, Oprah, Reese Witherspoon (and me!) — it’s worth a go for you too.

How would our lives improve if we changed our definition of success?

Success is a personal thing to define, but I would guess that a lot of people would shift their focus from financial or status measures towards more heart-felt things like family, relationships or community. We know from the advice of the dying that these are the things that drive happiness — no one dies wishing they had answered a few more emails. We would feel more fulfilled and reduce our reliance on artificial sources of happiness. Maybe we would even find we didn’t need so much money in the first place. We would be at peace with ourselves.

What’s the biggest obstacle that stands in the way of our redefined success? And what advice would you offer about overcoming those obstacles?

Social media is a massive threat to us living out our own definitions of success. We willingly engage with an infinite stream of suggestions for how we should be living and what we should look like. This makes our own mental space very crowded. I recently deactivated my personal instagram account and only spend time on facebook to be in my interest groups. Curate your social media very carefully if you’re going to spend any time on it and take regular breaks of several days, a week or more.

Where do you go to look for information and information about how to redefine success?

I look inside myself. The definition of success is personal. Don’t look outside. You won’t find the right answer.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she or they might just see this if we tag them.

UK Retail Superwoman Mary Portas. She said once on her podcast, The Kindness Economy, that she wanted to build a shopping mall of pre-owned items. I would love to tell her about our business that is doing that very thing online and build a partnership with her.

How can our readers further follow your work online?

I post regularly on our blog www.the2ndcircle.com/#blog. I am also active on linkedin. (www.linkedin.com/shelppi )

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.

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