Ditching the 9-5 Mentality and Finding Freedom In Your Work with Erin Halper, CEO of The Upside

March 17, 2021

Let’s talk consulting.

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It was 2001 and Erin Halper was living out of a suitcase in New York on her sister’s couch during the height of a tech bubble burst. She had big dreams to land a glamorous role in the city with a corner office, but ended up dabbling in fashion, beauty, and private equity before venturing into entrepreneurship and becoming the CEO of The Upside, an award-winning community and accelerator for consultants who want to achieve freedom in their work and say goodbye to the 9-5 lifestyle.

It was a pleasure to chat with Erin Halper in Episode 18 of the Career Memos podcast about her career journey and I can’t wait for you to tune in! Listen to the episode now on The Career Memos Podcast available on Apple PodcastsSpotifyGoogle Podcasts, and Stitcher


Your business may go through failure and various iterations at first.

Erin had always been super entrepreneurial and was drawn to starting her own consultancy after working at a beauty and accessories company and later kickstarting a career in the world of private equity, private investments, and hedge funds.

After witnessing so many friends stretching beyond their limits in their roles, while tirelessly commuting and parenting their children, she realized she had an opportunity: to help professionals build and launch their own consultancies.

The first iteration of The Upside was a total bust. In theory, it sounded great. She decided to match consultants with clients, because everyone wants to have amazing clients handed to them! Between having to rewrite biographies and seeing her consultants bomb a pitch interview to win over a client, it was discouraging work. Erin even reached a point where the business model no longer brought her joy.

What I love is that Erin chose to take a pause, rather than shut down completely. She realized the demand was there and a need was there, but if she simply reworked her business model, she’d have something special. This is how her membership and accelerator program came to life. 

If you want to run your own business, you have to be confident and risk averse.

Are you curious about starting your own consultancy? There is no less risky business to start. You can give consulting a try with next to nothing in start-up costs.

When you’re an employee, you’re betting on your boss and on the company you’re going all in with. You don’t have a lot of control over your experience. But investing in yourself has so many upsides. Erin says she can’t think of a better path to starting your own business.

Becoming a consultant is a learned skill, and it’s something just about anyone can do. While Erin teaches many of the basic principles inside of her accelerator (with a little tough love!), you don’t have to have a fancy college degree to be a successful consultant. No one is you, and that is your superpower. You just need a hunger and a drive to learn and to understand your value.

Even simply adjusting the language you use on client discovery calls and over email can help you claim your competence and confidence.

Developing your network will be key to your success.

One of my favorite takeaways from my conversation with Erin is about how valuable it is to invest in your network. In fact, Erin didn’t pour into her network until later in her career, and wishes she had started sooner.

Relationships will always open doors for you. And it’s so important to keep it personalized, authentic, and non-transactional.

Once a year, Erin will send a batch of 50 personalized emails to people in her network – to check up on them and see how they’re doing.

More about The Upside

The Upside opens up their early stage accelerator program 4 times per year and accepts 30 participants per round. Everyone in Erin’s accelerator identifies as a service provider. Some are industry experts, others are executive leadership coaches or are rolling out B2B tech companies. It’s a tactical experience with self-paced curriculum, live coaching calls, and a Facebook Community.

You can join the waitlist for Erin’s accelerator program here.


“You have to make a decision whether or not you’re going to invest in yourself, or in somebody’s company. When you’re an employee, you’re betting on corporate, you’re betting on corporate to have your back, you’re betting on corporate to pay you without any gaps, to pay you fairly for your knowledge and value. You’re betting on something you really don’t have much control over, versus betting on yourself and investing in yourself, which you do have control over.”

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Over the last 12+ years, I’ve done everything from work as a global human rights activist to lead marketing & partnerships initiatives at companies like Postmates and Apple. I’ve started businesses, lived in multiple cities around the world, pivoted careers more than once, and know what it takes to turn career goals into a reality. As a career coach & consultant, I’m passionate about sharing all that I’ve learned with you, helping you define tangible goals, and providing you with the tools and direct feedback you need to achieve them.

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