Oh, 2020. How best to summarize this year? The best I can muster is this: 2020, the year when much of life stood still while simultaneously much of life changed. What a paradoxical journey it has been.
I write this lead in reflection of all we’ve gained and lost as an entrepreneurial community. Some entrepreneurs witnessed their business models erode or implode, while others experienced demand for suddenly urgent products or services. Entrepreneurism itself is also more divided: Becoming an entrepreneur has never been more popular, but this trend suggests entrepreneurism is being pursued less out of purposeful ambition than basic necessity.
Mindful of this messy reality, we at SPI are incredibly grateful for our circumstances, and for all of you—our fans, friends, students, members, partners, confidants, and allies. While small businesses have bared the burden of the pandemic's economic carnage, our small business is doing okay. Our gratitude, however, is offset by our grief for those small businesses that haven’t fared as well.
To mark this moment, we captured our thoughts on what this year has meant to us and what we're looking forward to next year. Our individual perspectives are varied but also reflect a shared humanity and hope for us all, as humans and small business people. I hope you'll join us in reflecting on 2020’s highs and lows as we prepare for a resurgence of life, togetherness, and prosperity in the year ahead.
On behalf of everyone—Andrea, David, Jessica, Jillian, Jonathan, Karen, Mindy, Non, Pat, Sara Jane, and Ray—my great thanks to each and every one of you for being here with us this year. We'll see you on the other side.
—Matt Gartland, SPI Co-CEO
Here's who you'll be hearing from:
What was your work highlight of 2020?
I'm incredibly thankful to work for a company that is generous and caring. When COVID first happened, we offered one of our paid courses, Smart from Scratch, for free for over nine months. Knowing that we were helping people who were struggling due to job loss was very fulfilling. —Karen
My highlight is joining the SPI team and quickly confirming that the work environment is equally as kind and positive as it is fast-paced and ambitious. I'm so thankful to be a part of this group of people. —Jillian
The launch of SPI Pro—our private, invite-only community for committed entrepreneurs—could not have come at a better time. Well in the making before COVID-19, SPI Pro launched in July and immediately exceeded all expectations. To witness such compassion and generosity spring to life within our community of hundreds was a much needed upswell for our members and an equally needed source of satisfaction and joy for us. —Matt
My work highlight of 2020 cannot be pinned to a singular event. Rather, it's a culmination of small events, ultimately leading to the closeness we all now share. The moments that stand above the rest are the conversations and discussions that happened in between those “big” events—planning meetings, workshops, and brainstorming sessions—as our team moved toward an epic end-of-the-year project. —Jonathan
It's been a wild year! For me, the highlight has been moving into podcasting full-time and getting to really invest in that area of our business. We brought on a new podcast producer and together he and I have begun to build out big plans for the coming years (yes, years!). —Sara Jane
I started out this year on maternity leave. I am so grateful to work for a company that understands the needs of new parents. It's not easy for a small company to offer maternity leave, and it requires even more leadership to truly protect that time off for the employee. It meant the world to me to know that everyone at the company supported me in taking that time, even though it added extra work to their plates. —Mindy
My work highlight for 2020 has been being part of an incredibly supportive team during such an enduring year. We’ve come together to ask difficult questions around topics like the pandemic, racism, politics—and talked about what we can do to support our communities during these times. I feel so grateful to be a part of a team that is eager to tackle challenges head-on and work for a better future. —Andrea
Launching SPI Pro was incredible. The membership community wasn't even on the radar for 2020, but things changed after the pandemic hit and we noticed how much people were starving for connection and opportunities to network (especially with in-person events gone). And as we all know, we needed more support from others this year than ever. To see the entire team come together to push SPI Pro ahead, and to launch it with now hundreds of members, and raving testimonials, makes me so happy! —Pat
I'm grateful to be on a team of caring people who acknowledge and care deeply about the current state of the world and want to make it better. 2020 was a heck of a year, and to be part of a culture that truly values the health and wellbeing of its team is everything right now. —David
Rejoining Team SPI full time after being part time and freelance with the team for a couple of years. I'm excited for what we have in store as we round the bend on this unbelievably challenging year. —Ray
What was your work lowlight of 2020?
In the midst of everything going on in the world right now, I'm really grateful for my job and the health of my family. That being said, one of my biggest work-related disappointments this year was that we had to cancel all of our team summits due to COVID. —Karen
The lowlight that stands out the most was the loss of all human collaboration. Pat and I couldn't meet in person to talk big picture. I couldn't meet with the team to advance on plans and projects, or with partners to explore opportunities. Virtual collaboration works well, but often not well enough even for an online, remote-based company. Our goals for this year were compromised as a result, which limited our ability to positively educate, train, and support as many entrepreneurs as we might have. —Matt
My work lowlight can be pinned to a singular moment: when we stopped going to the brand new office. Yes, no one likes commutes, and parking could be a pain. However, there is something special about working shoulder-to-shoulder with those on your team that is lost online. While my productivity benefited from working totally remote, I also lost something I looked forward to. —Jonathan
Since our team is fully remote, we usually get together in person at least once a year, but due to COVID, we haven't been able to do that in 2020. I work with an incredible bunch of humans, so it's a great disappointment not to get that time with them. I'm hoping we'll get to make up for it in 2021! —Sara Jane
I missed all our opportunities to meet with #TeamFlynn in person, both at ConvertKit's Craft + Commerce and at FlynnCon. I was planning to bring my family to both, so that they could experience what an enthusiastic, creative community we belong to! My favorite part about FlynnCon01 was the conversations at our team booth, especially the on-the-spot troubleshooting I could do to help community members with problems, and I regret not getting to do that again. —Mindy
The lack of in-person interaction. It can be difficult to form authentic connections with peers virtually, especially if you’re new to a team. You miss out on the high-fives, the hugs, the laughs, the challenges that bring you closer—the experiences in general. The moments you have connecting with your team in person last a lifetime, and it has been tough to not have the opportunities to create those memories this year. —Andrea
A big lowlight this year was the cancellation of FlynnCon. With how amazing it was in 2019, it was something I was absolutely looking forward to and already in the middle of planning before we decided to delay the conference until 2021—and with where things are, who knows whether it can happen in 2021 as well. A real bummer, especially because I continue to hear how life changing 2019's event was for many of the attendees. —Pat
Having only been back with the team for two months now, I can't say that I've had a real lowlight this year 😉 —David
We had lots of events planned both on the road (accompanying Pat's speaking engagements) and here at home in San Diego. It has been very hard as the months tick along to acknowledge the milestones we missed. —Jess
The lack of in-person… anything, whether joining the team at FlynnCon or our annual retreat, or camping out at a local coffee shop for a midweek work session. I'm kind of an extroverted introvert, so I love to be around other people at least some of the time. I can't imagine how the real extroverts are dealing with all of this! —Ray
What entrepreneur stories from the SPI universe inspired you the most this year?
We've featured many entrepreneurs on the SPI blog this year, including Josh Hall, a designer who has turned his web design skills into a $250K/year business by creating online courses and a podcast to teach other designers. It's inspiring to hear stories of people who have started from scratch, and who now have a thriving business. —Karen
I'm biased, so I think the SPI Pro October Challenge of the Month, where we challenged our SPI Pro community to create sixty-second pitch videos, was the most inspiring! Seeing entrepreneurs step out of their comfort zone and be vulnerable for the sake of growth is so amazing, especially once it's all over and they realize how much they learned in the process! I love watching our Pro community continue to up-level their businesses. —Jillian
It's difficult to name just one story that stood out. As a group, the stories of upstart entrepreneurs displaying resolve and hope in the face of adversity this year are the most memorable and motivating for me. We've witnessed many of those stories within our SPI Pro community, and from time to time on Pat's AskPat show. It's always easy to point to big success stories as the most inspiring. While such stories are deserving, I harness far greater energy and determination from the entrepreneurs who display real grit. Bravo to all those who haven't given up or given in. —Matt
Our “Black Entrepreneurs Speak Out” series. In listening to their stories, I could hear the resiliency and determination in their voices. Across different countries, backgrounds, and religions, this series was moving and inspirational. —Jonathan
I've loved reading the success stories on the blog. Getting to read about audience members' personal stories and put faces to names has been a joy. —Sara Jane
My favorite entrepreneurial story comes from one Deborah Niemann at ThriftyHomesteader.com. She is an incredibly involved SPI Pro member, and an expert on raising goats! I love when I see Deborah in one of our calls, because the examples she shares from her business are simultaneously so different from my day-to-day experience of online business, but also so much the same. —Mindy
This is a tough one to narrow down! In general, the most inspiring stories this year for me have come from the SPI Pro community. So many entrepreneurs joined our community and opened themselves up to vulnerability so that they could grow and improve their businesses. I’ve had the opportunity to watch entrepreneurs in SPI Pro step out of their comfort zones to achieve milestones they didn’t think they were capable of. I’ve also had a front seat to watching these entrepreneurs support one another genuinely—the whole experience just reminds you that together, anything is possible. —Andrea
I really enjoyed Casanova Brooks' story on the SPI Podcast (Session #451). That he was able to overcome all he has and actually use the low points of his journey as fuel is remarkable and super inspiring. —David
Even though I'm a proud auntie (not a parent), I really enjoyed everyone's stories from SPI 419 in April about how things have changed since having children. I always enjoy AskPat “Where are they now?” episodes where we get to hear progress from our past coaching call guests and how things have evolved since Pat last spoke with them. —Jess
I had the pleasure of interviewing and writing about a handful of inspiring entrepreneurs this summer for the SPI blog. From Rebecca Dekker's education and advocacy for better birth experiences, to Kolarele Sonaike's communication-skills side hustle and mentor-leadership in the Black community in London, and Nalin Chuapetcharasopon's crowdfunding consultancy, it was so cool to learn how entrepreneurs are making it work and serving their audiences in this mess of a 2020. —Ray
What are you most looking forward to in the world of work and entrepreneurship in 2021?
I'm looking forward to seeing the continued innovation that entrepreneurs dream up to improve the human experience during the pandemic and beyond. —Jillian
2020 has been a year to endure. To not break. To not quit. To not let extrinsic forces and circumstances overrun our values and ambitions. 2021 is the year we flip the script and take it back. To reclaim more of ourselves and more fully live out our work, which is to say, our purpose. I do not feel it's possible to comprehend in real time the depth of all that has been suppressed this year—or to overstate what can be achieved next year with a reinvigorated human spirit. —Matt
Watching businesses that began because of COVID-19 work to grow beyond a business of necessity, e.g., what will successful mask companies do when masks are no longer used on a daily basis? —Jonathan
I'm really looking forward to and have great hope that we will return to some form of normalcy by the end of the year that will allow us to interact in person again—either as a team or gathering at conferences again. I'm also looking forward to forging ahead on the podcast front! —Sara Jane
I am looking forward to creating more video content, as well as learning from other team members the best strategies for creating that content. I'm a huge consumer of video tutorials, and I'm eager to contribute to the genre. —Mindy
I’m looking forward to seeing entrepreneurs and business begin to challenge the norm (in terms of operations) as the economy works toward stability. Throughout the pandemic, several businesses quickly learned that remote teams can be successful, which I think will open up opportunities and change the way we work. In the same vein, businesses have started to uncover and acknowledge the importance of mental health in the workplace. Many businesses have adopted summer hours or integrated wellness into their benefits to help employees maintain a healthy work/life balance. I’m excited to see this momentum continue in 2021! —Andrea
I'm looking forward to seeing what the podcast team cooks up in 2021 (and that's all I'll say about that for now). —David
I cannot wait to host more events here in San Diego. The entrepreneurial community here in SoCal is incredible, and we have missed connecting in person so much. —Jess
As senior writer, I'm contractually obligated to say “the SPI blog“—and we've got some great stuff brewing there—but I'm also psyched about what's coming down the pike with our stable of podcasts. Stay tuned! —Ray