The Upside

What I learned in 5 years of running The Upside

It’s hard to believe that this week I get to celebrate The Upside’s fifth anniversary!

I started The Upside in 2017 because I had a nagging drive to make an impact and change the way working works. Quite frankly, I’m kind of pinching myself that The Upside has made it this far.

I owe our success to doing a few things right, including:

  1. Leading with impact and a social mission
  2. Listening to our members
  3. Focusing on quality over quantity
  4. Showing up as my full self
  5. And seeking advice from people who want me to succeed

But as wonderful as it all is today, The Upside didn’t start out so rosy. In fact, during the first two years of The Upside, I was busting my hump to build a business model that I eventually gave up on: a talent agency matching consultants with corporate clients.

It didn’t work.
There wasn’t enough demand.
The market wasn’t ready for it.
The consultants needed training.
I spent the majority of my day negotiating contracts.
…and I loathe contracts.

Because I hated that business (and it hated me back), The Upside community was born. Three years later, The Upside is a 200-strong community of top independent consultants, advisors and experts who join forces to advance their businesses.

It’s truly magical and I LOVE it.

But no entrepreneurial road is smooth and, like every founder, I’ve experienced countless ups and downs, highs and lows, good days and bad days, wins and losses.

If I could go back and do it all over again, here’s what I would change:

  1. I spent too much time looking at the competition.

There’s no point in comparing yourself to others. They have their own journey and it’s not yours. Instead, focus on what you do best and doing it better than anyone else.

  1. I didn’t charge enough in the beginning.

You can raise your prices anytime. But you can grow faster and leap further if your prices reflect your goals and value from the beginning.

  1. I didn’t invest in branding and messaging as early as I should have.

Professional branding seemed like a nice-to-have for a really long time. But, when clients don’t understand your what, who and why, it causes so much unnecessary work to get people over the goal line. I should have rebranded much sooner.

  1. I got sidetracked by shiny object syndrome.

There are always going to be exciting opportunities and possibilities in entrepreneurship. But if I could go back, I would have been a whole lot more disciplined instead of thinking about what’s new, what’s next and what’s possible.

  1. I didn’t take care of ME.

My needs always fell to the bottom of the list. That has since changed, and I’ve never been more productive, happy and fulfilled in business.

Thank you for being part of this journey and believing in The Upside.

Erin Halper

About the Author

Erin Halper is the founder and CEO of The Upside and the leading authority on independent consulting. Since launching The Upside in 2017, Erin has helped thousands of professionals transition from corporate life into consulting to achieve flexibility, autonomy, and a renewed sense of purpose in their careers.

Erin has been a frequent speaker at Columbia, NYU, Harvard, and Brown and has been featured as a leading future of work expert on dozens of podcasts as well as in Forbes, Business Insider, Nasdaq, Crunchbase and many more.

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