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Why I Need to Say “Yes” More in Business

...and nine other unexpected things I learned in year one of my startup

Erin Halper, Founder & CEO of The Upside
I officially launched The Upside in May, 2017 to bridge the gap between high-achieving professionals seeking more balance and flexibility in their careers and businesses that can benefit from best-in-class, scalable, flexible and on-demand talent. Wrapping up my first year as a mission-driven, self-funded startup, I reflected on what was achieved, opportunities that were missed and, most importantly, what I learned:

(1) I need to say “yes” more.

It’s just soooo easy to say no. The timing doesn’t work. I won’t be able to see my kids that night. I’m too tired. It’s too daunting. It’s so much trouble. But a few months into the business I decided that, regardless of time constraints, I would say yes to as many opportunities as possible. Saying yes opened unimaginable doors for me, including speaking at Brown University, participating on panels discussing topics I’m passionate about, attending workshops and dinners with other founders, making dozens of new business friends and attending a mastermind retreat in Woodstock, NY. Saying yes has served me and The Upside quite well!

(2) It’s important to surround myself with likeminded people.

When I first started The Upside, I had very few friends who were involved with startups. Even for the small infrastructure-related questions, I had only a handful of people to turn to. Then I joined a business group for women founders and leaders and my business literally took off. I finally had a resource of women to learn from, lean on and count on. And I continue to tap into that resource as I grow in year two.

(3) Approach every situation with a critical eye and ear.

The best thing I did for myself in year one was to look and listen. What worked? What didn’t work? What is the person on the other end of the phone really trying to tell me? Every day brought me a new case study to analyze which helped form best practices and a strong infrastructure to propel the business forward in year two.

(4) Comparing brings no good.

It’s so darn easy to compare yourself to others when you’re trying to build a business. They look more successful. They look like they have more revenue. Better marketing. Better publicity. Better hair. It’s never ending. But ultimately, it doesn’t matter. Let’s face it: only the founders and their accountants really know what’s under the hood anyway. I’ve learned to stop comparing and keep my focus on my business and its achievements.

(5) Be open to new ideas.

As a startup, it’s important to consider additional models and revenue streams that may make sense for the business. For example, we were often asked for a community platform for our consultants to discuss business and help each other grow. However, the launch date kept getting pushed (and pushed) because we are so focused on developing The Upside’s main model. Which brings me to…

(6) Don’t stray too far from the original business model.

Ultimately, I launched The Upside with a specific mission in mind: to disrupt traditional hiring practices and change the way working works in corporate America. Based on this mission, I designed the business model with a ton of research and intention. Some of the opportunities that have come our way overlap with the primary model, but ultimately spread us too thin, taking away from that original mission. So…I guess sometimes I’ve had to learn when to say no, despite lesson #1 above.

(7) Have your infrastructure in place as early as possible.

A month after launching the business, I posted an intro on a Facebook group with the intention of attracting a few key consultants early on. What resulted was 200 emails and messages in one week, and my lack of bandwidth to handle them all. From that point forward, I created a stronger infrastructure to handle large volumes of inquiries and better communications for explaining the process of working with The Upside.

(8) Speak to anyone and everyone who will listen.

The guy next to me on the airplane. A friend I haven’t seen in 10 years. My nextdoor neighbor. Every person who hears my mission is an opportunity for a referral, an idea or feedback. In fact, I’ve received helping hands from some very unlikely contacts! If you are within 2 feet of me, you will not walk away without knowing what The Upside does. You’ve been warned.

(9) The kids will be fine.

I used to worry so much about being home in time to cook dinner or volunteering enough at the kids’ schools. And of course I still think these are important contributions. But I no longer stress about them. The kids will be just fine. If anything, I’m setting an example for my two sons who are seeing their mother pursue her dreams and their father contributing equally in the home so that The Upside can make the much-needed changes in the way working works in corporate America. And to my sons’ future spouses, whomever you may be: you’re welcome.

(10) Set big goals.

What’s the point of putting your heart and soul into a business if you set the bar at mediocre. Yes, a big milestone is recouping the initial investment. But beyond that, the sky’s the limit. I’ve learned to set big goals, including personal goals such as writing a book and doing a Ted Talk. What’s to come in year two? Just you wait and see!
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