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How These Small Business Owners Learned To Let Go

In order to grow their companies, these entrepreneurs learned to let go of outdated beliefs that no longer served themselves or their businesses.

Nov 15, 2022 9 min readSmall Business, Big Lessons
Photo of Umber Bhatti
Umber Bhatti

Content Writer @ Buffer

Small Business, Big Lessons is a podcast from Buffer that goes behind the scenes with inspirational small businesses to explore how they are questioning the best ways to build a business and uncover the big lessons we can learn from their journeys (so far). Check out episode eight here.

Running a small business requires grit and perseverance, but these entrepreneurs found in order to really succeed they needed to relinquish certain beliefs that they once held close. In our final episode of season 2 of our podcast Small Business, Big Lessons, we spoke to several entrepreneurs about former thought processes they had to leave behind in order to grow their small business and why that was the right decision for them.

Why letting go is important for these longtime entrepreneurs

Letting go of previous viewpoints is never easy, especially when it comes to beliefs or ideas we’ve held for a long time, but according to business consultant Holly Howard sometimes entrepreneurs can get too attached to certain beliefs and need that push to let go. She finds author Katie Byron’s concept of asking oneself “Is it true?” is a great way to think about whether some of our ideologies are still relevant today.

Holly shared, “’Is it true,’ is a helpful way to sort of play with this idea of letting go with entrenched beliefs. Because sometimes, when we are challenged around our beliefs, we can get really triggered, right? And we can double down and we can hold tight to things, because those beliefs have been our safety.”

Checking in with yourself and evaluating whether your beliefs are relevant and whether they still resonate can help from becoming stuck in a certain mindset. Seasoned entrepreneurs Rand Fishkin and Ari Weinzweig have learned the power of letting go early on in their careers and say it’s helped them immensely in all aspects of their lives.

How one entrepreneur practices detachment

Rand Fishkin, co-founder of audience research tool SparkToro, finds letting go a bit easier than most people do. The entrepreneur says he’s developed an unusual detachment from previously held beliefs and prior ideas, and even has learned to not get too attached to the sentimental things in his life. He credits this to his maturity and that fact that he’s able to rationally reason about things – even when emotions are involved.

When it comes to his past experiences as a small business owner, Rand does have some regrets. Specifically from his time as CEO of his first business Moz, a SEO software company. Looking back now, Rand believes he valued the wrong things when running Moz, like having a big staff, a huge IPO, and raising lots of money. Now, he thinks the opposite is true, and is running SparkToro with different values, including smaller team sizes.

“I have so many things I regret from my time at Moz. And also, I'm deeply grateful for the experience. And I think those two things can be tough to reconcile, but they can simultaneously exist and you can still be at peace,” he said.

While it’s not always easy for Rand to reflect on his former business, he has chosen to forgive himself from his past mistakes and has let go of any deep feelings he has about the time. This has allowed him to start anew with SparkToro.

Still, he understands that forgiving oneself and detaching from past experiences isn’t always an easy journey. But he believes that, eventually, anyone can get there.

“I think people who have gotten to that place [of letting go], have gotten there through active work on it,” he said. “Through emotional processing, and the ability to reflect on their actions and reflect on the life they want to lead. How they want to be in the world and the impact they want to have on people around them.”

Viewing letting go is an essential part of life and business

Ari Weinzweig, co-founder of Zingerman’s community of businesses, believes that once we become conscious of our beliefs, we are free to unlearn them or choose beliefs that are more compatible with our lives. This philosophy around letting go has allowed him to succeed as an entrepreneur but in his personal life, too.

Thinking back to his childhood, he can pinpoint certain beliefs that have benefited his life and others that he’s had to confront.

“I love to read. So this is something I grew up with. And that belief that I got when I was two has served me really well,” Ari said. “Other beliefs, like that asking for help was weak, were very unhelpful. And so I've needed to relearn how to do that.”

Similar to Rand, Ari also learned to detach himself from Zingerman’s. He tries not to let past failures with the business define him. He takes insights from author Carol Dweck’s book, "Mindset: The New Psychology of Success," and believes that everyone is a good person who is trying their best. By operating with that mindset, Ari views failure as a necessary component of life.

“When we embrace imperfection, then of course, I make mistakes. Of course, not everything's going to work out. And then I need processes, techniques to help myself reground because there's failure happening constantly in the ecosystem,” Ari said.

How these entrepreneurs had to let go in order to start their small businesses

Here's what these entrepreneurs had to let go of in order to go all in with their small businesses.

Leaving full time jobs to pursue a passion

When Becky and Huw founded Paynter Jacket, an ethical clothing store that drops four jacket releases a year, they were both still working full time jobs while running their small business on the side.

They did this to be cautious and not put all of their eggs in one basket, but eventually, as they started gaining social media followers and released their first batch, Becky decided to quit her job. She left on her birthday as a gift to herself. Letting go of the stability that a job provides was nerve-wracking, though she was also excited for the future of Paynter.

“I think it was lucky that I waited until after batch number one [to quit my job], because we had customers and we really did have a lot to do. It was everything I'd wanted,” Becky said. “And it was also really intimidating at the same time because you don't have a boss or a mentor that you have in a bigger company that you can say I'm struggling with this, or can I just check this with you?”

Soon after, Huw took the plunge and quit his job, but letting go was a bit more difficult for him, especially because he really appreciated his work environment and colleagues.

“It was actually really hard for me to leave my job because I was in a company that I absolutely loved,” he said. “I loved the people there. I loved the purpose of the business. I loved doing my job every day,” Huw said. “It was hard to even think about leaving because like, this whole team around me, I absolutely loved them.”

It was Huw’s boss and mentor who finally gave him the push he needed. He sat Hu down and told him he believed in Paynter’s success. And also reminded Huw that he was at the perfect stage in his life where he could take the risk and go out on a limb.

While letting go of jobs that provided stability and comfort weren’t easy for Becky and Huw, doing so was the only way they were able to put their all into Paynter Jacket.

An evolution of a career path

Before Kelly Phillips founded Destination Unknown Restaurants, she was working full time as a journalist and food writer. It was through her day job at the Philadelphia City Paper where she was able to learn the ins and outs of the restaurant industry that made her interested in opening up one herself. While switching careers to owning restaurants instead of simply writing about them may seem like a big jump, Kelly sees it as a natural evolution of her career path.

“I think this is my story. I think I was meant to open restaurants and I was meant to be this person, I still get to tell a story in a different way.”

This career change has helped Kelly let go of limiting beliefs she once had about herself. As a writer, she never felt confident about her public speaking abilities, and felt more comfortable putting pen to paper. But after founding Destination Unknown Restaurants, she’s been invited on podcasts and has participated in multiple speaking engagements.

“Writing brought me a lot of happiness, seeing an article published in the newspaper, I would be really proud of that. But I think what I'm doing now is more of a challenge for me, it's harder for me and it's less comfortable for me. And because of that I've grown and become a better person,” Kelly said.

Letting go of comparisons

Founding a start-up is never easy, especially when you’re living in Silicon Valley and are surrounded by hundreds of other start-ups. Andrea, co-founder of Harlow, a small business with the mission to help freelancers get organized, has learned to not hold herself to the standards of what everyone else is doing in the industry.

“I live in San Francisco, I'm in the heart of startup tech culture here. And a lot of times success is measured by funding by how much money you've raised, by how many employees you have. And it's definitely a work in progress to remind myself that that's not our measure of success and come back to our core beliefs and our values and that we're building something different than a lot of people in Silicon Valley. And that's okay.”

By choosing to not compare their business to other tech companies, Andrea is letting go of traditional startup values and instead embracing what makes Harlow unique. This has allowed her to dive into her small business and run it without being constricted by other people’s input and ideas.

How letting go has allowed these small businesses to reach their highest potential

For many entrepreneurs, letting go of certain mindsets was an essential part of starting their brands. But, the learning never stops. Throughout the course of their small business journeys, these leaders have had to let go of old habits and ways in order to successfully grow their companies.

Realizing the power of teamwork

When Joel first founded Buffer, he held the belief that, as a founder and CEO, he alone would have the answers to all of Buffer’s problems. But eventually, as the company grew (we now have over 80 team members), Joel realized that he needed to let go of this notion that he himself could do it all on his own.

“I think I've had moments where I might dip back into that and be like, ‘okay, this isn't working. I'm gonna dig in and solve this,’” he said. “I think I've had to let go of that being the way to solve things and lean much more into communication and getting everyone aligned and onboard and understanding the vision.”

As an introspective person, Joel still often takes time to reflect on situations by himself, but has learned to share his thoughts and reflections with the rest of the team. This creates an environment at Buffer where everyone is on the same page and has a chance to speak up on key issues.

Letting go of the need for praise and accolades

Initially, Kelly was focused on the reviews, accolades and stars she could receive for her food when she first opened her restaurants. But once she took a step back and focused inwards, she noticed that her business was improving internally.

“And I think when I let go of that, when I stopped putting that pressure on myself, and I focused on just being a great restaurant in our community, and a great place to work for our team, I think that's when the restaurant actually clicked. That's when things started to work,” she said.

Instead of thinking about the press and other external factors, Kelly honed in on the important things: that the business was profitable, her employees were happy, the food was good, and customers were having a great time. Looking at things from this perspective ultimately allowed her restaurants to succeed.

Being flexible and open to shifting one’s perspective

Samantha and Andrea had a specific vision of their community’s needs when they first opened up Harlow. But once they started getting more and more clients, they realized they’d have to let go of the idea that they understood all of the obstacles their users faced.

“One of the most humbling things about building Harlow is recognizing that Andrea and I's pain points as freelancers are not the same pain points that all freelancers are experiencing,” Samantha said.  “So just recognizing that this audience is very diverse, and they have a lot of needs, and that there are a lot of different ways that they do things.”

If the duo were set in their beliefs and unable to pivot in their thinking, they wouldn’t be able to support the various freelancers who use Harlow today.

Ultimately, letting go of certain beliefs can allow for a healthier and more sustainable business. While some beliefs may stand the test of time, more often than not, entrepreneurs have to be flexible and open to switching things up in order to grow their business to its highest potential.

Want more on letting go? Check out the full episode

The businesses we interviewed in this episode have further insights to share about taking a stand and its value for brands. Listen to the full episode here.

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