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Yes, it’s totally possible to have a more flexible career.


I’m really lucky.

I’m in this rare situation where I get to build Work Bigger while I work part-time at the largest news organization in the world.

The benefits? I have income coming in, I can help support my family, and I can build my business while managing the risk involved with entrepreneurship.

It’s incredibly difficult to find a part-time job, never mind a part-time job with benefits, a 401K and vacation days.

How is it possible?  I negotiated this role. It took a lot of work, but I wasn’t going to let up.

Flexible work situations are becoming more and more critical. As millennials get older and we become parents, we need flexibility to build our careers while we support our families. Why should we have to give up on either dream?

And even if parenthood isn’t in your future, you likely value your freedom. You want some say in structuring your day, and sitting at a desk for 8 hours a day does not make you a committed, brilliant employee. On the contrary, it likely adds to your exhaustion and reduces your productivity.

So what do we do?

Meet Erin Halper, the founder of The Upside. The Upside creates more flexible work opportunities for women by connecting them with businesses that embrace the benefits of hiring flexible talent.

In this interview, Erin and I talk about how you can make your work work for you, whether you’re in a 9 to 5, a freelancer or a new entrepreneur. This is especially important if you’re feeling stuck in your career in ANY way. In today’s evolving workplace, we have more options than you realize.

Give us some background. Where are you from, and where did you start out?

You can call me a walking stereotype: small town Southern girl moves to NYC to take on new adventures and “make it big!”

I grew up in Spartanburg, SC and always set my sights on moving to the big city. In 2001, after finishing college in Washington, DC, I followed my big sister to New York and took whatever job I could find, just to get started.

I had no family in New York (other than my sister) no connections, no network and no safety net. Just a lot of heart, a pair of bright eyes and a bushy tail, and even more hustle.

After three weeks of sleeping on my sister’s couch in a windowless studio apartment, I landed an assistant job at Frederic Fekkai’s corporate office, supporting the head of product development.

One could say it was a bit too similar to The Devil Wears Prada, although we did have a ton of laughs and really great hair while working there.

After September 11, 2001, the economy began to tank and my entire team was laid off. It was exactly the push I needed to hit the reset button, since I knew this path wasn’t for me and life suddenly felt all too short.

My next chapter: private equity. I landed an analyst role through a GW alumnus I met through friends, and the rest is history.

I spent my entire career in the alternative investment space and built a niche for myself as an expert in marketing various funds. I was able to spin my career into a consultancy and took on various investment clients for 7 years before deciding to launch The Upside.

What is your mission, the work you want to do?

My mission is to provide more independent work opportunities for high achieving women who would otherwise drop out of the workforce or suffer miserably at a full time (or what I call “facetime”) demanding job for lack of flexibility.

On the flipside, I aim to provide businesses access to this incredibly fragmented and highly untapped pool of best-in-class, flexible, scalable, on-demand and part-time talent.

It’s truly a win-win!

What led you there? Can you recall any experiences you had that pushed you to your mission?

There have been two major pushes that led me to my mission. The first came to me before I started working as a consultant. I remember sitting in the office on a beautiful August day, realizing that all of the senior partners were out on vacation and pretty much no business was getting done.

I thought, “I don’t want to be here pushing papers around my desk to look busy when I could be enjoying the day. I just want to work efficiently and be paid for my time.” That’s when I started my consultancy.

The second push was when my friends and I were starting families. I began noticing all of these smart, accomplished women I knew from college or work struggling—I mean REALLY struggling—to hold onto their careers and figure out some type of solution to achieving more flexibility now that they had young families.

They didn’t want to quit, but they couldn’t justify working full time anymore with small children at home. It just didn’t make sense to me that corporate America was willing to let these talented, dedicated and incredibly efficient workers leave.

I kept saying, “Why don’t you consult?” to which women answered, “I don’t know where to start,” or “My industry doesn’t hire consultants,” or “My skillset doesn’t translate into a consultancy.”

I also witnessed many of these women joining multi-level marketing companies like Rodan + Fields or Stella & Dot which promote themselves as the perfect life/work balance for women. In the end, I saw a real hole in the market that needed to be filled. And I’ve been determined to fill it ever since.

Can you share with us how The Upside solves this problem?

The Upside creates more flexible work opportunities for women by connecting them with businesses that embrace the benefits and efficiencies of hiring flexible talent.

Our take is that corporate America is still many years away from embracing the concept of a fully integrated flexible workforce. For many women who need flexibility now, several years is just too long. That’s why we have a consultant/independent contractor model in addition to our part-time employee model to help companies ease into the idea of hiring flexible workers.

As a consultant matchmaker of sorts, we know from the placements we’ve already made that employers quickly see the efficiency and returns from working with an expert contractor, resulting in a shift in how they view traditional hiring practices.

In fact, it’s been proven time and time again, study after study, that when workers receive the flexibility they need, employers experience easier talent acquisition, better performance, increased loyalty, higher productivity and improved morale across the board.

What challenges did you face along the way, and how did you overcome these challenges?

The biggest challenge is educating the marketplace as to the “what” and the “why” of hiring high-level independent contractors and consultants. There is still this value businesses place on face time, which absolutely alienates so much talent.

For companies that open up, even just a little bit, to the idea of hiring an expert part-time vs. a mid-level employee full time, they will open their doors to a flood of untapped, highly pedigreed talent that they never had access to before. And they will never look back.

I think every company like mine entering the flexible work category faces this challenge. And together, we are all working hard to educate businesses through in-person meetings, press, speaking opportunities and interviews.

Whatever it takes to get the message across that flexibility is good for women, it’s good for men, it’s good for diversity, it’s good for business and it’s good for the future.

For women who are feeling like – well my skill doesn’t translate to a consultancy – what can they do to change their mindset and their situation?

We speak with many women who just don’t see how they can consult based on their background. It’s true that some roles, like being a trader or a litigator, are more of a challenge than a marketing director or accountant.

However, no matter your background, there is always an opportunity to consult if you follow one of these paths: (1) focus on a specific skill that you bring to the table and create a value proposition around that unique skill that can be pitched to clients or (2) think outside of your job experience by combining your personal experiences and passions with your existing skills.

For example, just last week I was speaking with a woman who came from a bond sales background. She claimed there was no way she could consult with her background, and proceeded to explain the limits of her industry. She had recently quit after more than 15 years of blatant abuse by male colleagues and superiors, as well as losing her book of business to male colleagues after returning from each of her two maternity leaves.

Then she made a joke that she could be the poster child for harassment and discrimination culture on Wall Street. She saw the twinkle in my eye. Bingo!

I suggested she package that ex-Wall Street warrior who braved years of harassment and abusive corporate culture into a neat little box that can go into these legacy boys clubs and train them on inclusion based on her own stories and experience. She could even do a TED talk!

Her personal experiences combined with her career background give this potential consultant a unique value proposition to pitch to HR departments. And to think she said there was no way to consult with a background in bonds sales!

Are there any additional insights and trends you can share on the future of work? What should we keep an eye out for as the workplace changes?

There is power in numbers.

By 2020, it is predicted that more than 40% of the U.S. workforce will be freelance. This is a figure that employers can no longer ignore. I often talk about the developing trend of talent assortment which is a company’s unique mix of full-time employees, full-time flexible employees, part-time employees and independent contractors to build business efficiency and cater to a diverse workforce with varying needs. At The Upside, we are seeing a slow trend towards a more balanced mix of human capital categories as companies finally start to see the increased bottom line benefits.

Additionally, and again slowly, women are starting to speak up and ask for what they want. From the #bettertogether movement post-election to the #metoo movement post-Harvey Weinstein, women are finally saying enough is enough.

This applies to everything from discrimination in the workplace to lack of flexible job accommodations for those who request it. There are more and more articles arming women with the right tools to have a professional conversation with their employer about flexibility. The more women speak up, the more employers pay attention. Power in numbers.

The future of work is brighter than ever. There are several startups entering (or really pioneering) the “flexible work” industry, all tackling the issue from different angles but with the same underlying mission of creating more flexible career opportunities for those who need it the most: women. Cheer each of them on. If we really want to move the needle for women, we need as many of them as possible to succeed.

What advice do you have for 20 to 30-somethings who want to make an impact through their work but are currently feeling stuck?

There are many ways to make an impact.

First, define exactly what impact you’re trying to make. Break it down into smaller milestones that are achievable.

For example, I’m trying to change the way working works in America. That’s a pretty tall order. So I’ve broken it down into smaller segments that I can achieve in steps, like first building a business model that makes an impact and makes money, then educating 5 – 10 businesses per week (that’s 500 businesses in a year!) about why they need to change the way they look at hiring, and so on and so on.

Stay patient and stay focused on your end goal. Most successful people will tell you that they achieved their goals through perseverance and grit. Making an impact is no different. Keep getting back up and keep your eye on the end goal.  

What’s the greatest insight you’ve learned from our interview with Erin? And what can you do to build more flexibility into your work situation? Share with us below.

Belma McCaffrey

Author Belma McCaffrey

More posts by Belma McCaffrey

Join the discussion 2 Comments

  • Erin Tarr says:

    THANK YOU for this! I am currently in that “trying to re-imagine how I can consult based on my experiences” so this was a timely and much needed article! Also the note about breaking down how I am changing the world into manageable chunks … working on that too! 🙂

    • Belma McCaffrey says:

      Thanks so much for your comment Erin! I’m so glad this resonated with you. 🙂

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