Entrepreneurial Seasoning
When I taught a free class on making more inclusive data visualization, I got a TON of responses that fell into one of three buckets:
- This class was AWESOME!
- I missed the class, where is the recording?
- This class was terrible, you were wrong on all these points, being exclusive with these suggestions, and neglected to mention these ideas.
It’s how I respond to the third bucket of comments that let’s me know what season I’m in with my business.
Expand or Contract Audience Season
My response, at that point in time, to the five paragraph paper of an email with bolded headings and numbered lists detailing my misgivings… was a chuckle. It’s nice that people are so passionate about such an important topic, I thought to myself.
I was in a season of wanting to expand my audience by offering new content, pushing people’s thinking, and getting comfortable being a lil controversial.
Without a doubt in my mind, I have also offered new, lightly controversial content in the past, where I got responses in all 3 buckets and my reaction to bucket 3 was fuck this shit.
I had been putting myself out there when I was in a contracting season. Good intentions, wrong timing for my spirit. All I wanted to do was scream I’m trying my best and If you don’t like it, go elsewhere – this was a FREE class.
That’s vastly different than a chuckle.
As important as it is to show up in the world with consistency, I’ve learned that I also have to watch out for changes in my seasons. Heck, I had to learn that I actually have seasons.
We all do.
Audience growth seasons are one version, but we go through others, too.
Expand or Contract Staff Season
When my staff finish a workshop and get an email like “It was truly one of the best and most practical training courses I’ve taken during my career.” it feels SOOOOoooooo good. Me and my staff just doing this at each other over in Slack:
I freakin LOVE having a team that can help me reach more people and get more good data viz out there in the world.
Teams bring a bigger impact.
You know what else teams bring? Problems.
Needs.
Management.
Which – of course! They need guidance from the boss. Makes total sense.
Despite ever better systems and procedures, from time to time I still end up being an absolute bottleneck for my business.
One option is to hire more help, like a COO, and expand even further. This is what Nina did.
It’s also perfectly ok to decide that sounds like too much work.
I’m not a great manager. I don’t even want to manage. I want to be the one in every workshop, passing out the high fives to my students. I have my seasons where I want to shrink the team and be a one-woman show.
But then I think about all the people I wouldn’t be able to help… And it’s like that, back and forth, forever.
Entrepreneurial Seasoning
You can probably identify other areas of your business where you catch seasonal feelings. Like growing or whittling the services you offer.
If you’ve only been in growth mode so far, hang on – winds will shift. That’s not a bad thing. Mary Poppins came in on a change in wind direction, after all.
Jereshia Hawk made a great point on her podcast: If you’ve only seen growth mode and your revenues have been jumping more than 30% each year, you might need to make yourself take a maintenance season.
Seasons can last months. Or hours.
It’s so tricky. So here’s what to do:
Recognize when a season is changing. You can usually tell by your reactions to common events.
Recognize that this is just a season. It won’t last forever. Take advantage of the season you’re in, while you’re there.
Do you have different seasons than the ones I listed out here? What season are you in right now? Email me – I can relate.
Staffing Up
Entrepreneurs who have the seed of an idea for a business ask me questions like How do you take the leap? and How do you get your first client?
Entrepreneurs who are sprouting have cleared those hurdles. Looking back, those seed stage questions are heart-warming: they’re real and sweet and entirely solvable and my gosh how quickly those worries morph into other pressing questions.
Sprouting entrepreneurs wanna know how to manage the massive incoming workload and how to staff up – carefully.
Nina Sabarre‘s sprouting business must have been sprinkled with Miracle Gro. Intention 2 Impact is only 4 years old but she’s already amassed huge clients like the Chan Zuckerberg Initiative and a deep bench of team members. In this quick interview, I wanted to ask Nina how she staffed up with care, while all that growth is still fresh in her mind.
STEPHANIE
Who was your first hire? And how did you know it was time to hire them?
NINA
My first hire was myself! After three years in business, I transitioned Intention 2 Impact from a Single Member LLC to an S-Corporation — which required me to become a W2 employee with a salary. In addition to tax benefits, this helped me prioritize paying myself monthly.
My second hire was equally important. I realized that I cannot sustainably scale I2I alone, so I brought on a business partner and Chief Operating Officer (COO).
STEPHANIE
Say more about that. What exactly does your business partner and COO do that you couldn’t do on your own? How, exactly, are they helping you scale?
NINA
My goal is to build a premiere, next-generation social impact consulting firm, and I have always known that I cannot do it alone. My business partner, Dr. Kathleen Doll, is the yin to my yang! As COO, she oversees the internal, daily operations, which allows me to focus on the big picture strategic vision of the company.
Stephanie, remember in 2020 when you encouraged me to take the Clifton Gallup Strengths Finder assessment? That is when I realized that my core strengths are in vision, strategy, and influence, and I am lacking in execution. Kathleen’s strengths are complementary to mine – which makes us an unstoppable team!
STEPHANIE
Yes! Ok but can you give some specific examples of internal daily operations vs big picture strategic visioning? You aren’t sitting around just thinking all day, are you?
NINA
I wish! At the beginning of each year, I put together our annual business plan (leveraging last year’s data and in alignment with longer term goals). In the plan, we identify SMARTIE goals for five categories of business: products & services, operations, finance, business development, marketing.
Kathleen owns the products & services and operations goals (i.e., what we do and how); and I own the finance, business development, and marketing goals (i.e., how we build to sustain what we do — rooted in our ‘why’).
In addition to BD & marketing, I tend to play a lead role in the beginning and end of projects. This typically means building client relationships, setting overall project design and strategy, facilitating sensemaking, and designing final products.
Kathleen is the real mastermind keeping the work on track and on time. She manages projects and consultants, and is incredibly skillful at high-quality execution.
Although we have our different strengths and distinct roles, we practically share a brain + heart! I am so lucky to be leading I2I with one of my best friends.
STEPHANIE
Your company has been growing tremendously over the past few years. Besides you and Kathleen, I know you’ve got a bench of associates. And an assistant? How did you know it was time to hire each of those people? And tell us if they’re contractors or employees.
NINA
In 2018-2019, the “company” was just me, myself, and I – working mostly as a sub-contractor for other firms. In 2020, I started bringing together independent contractors to go after direct contracts with ideal clients and grow I2I into something bigger than myself.
Over the past three years, we have had more than a dozen consultants work across ~30 projects. We have three types of engagements with our consultants:
(1) One-time consultants who work on a single project because of their unique subject matter expertise
(2) Go-to consultants who have worked on more than one I2I project and can be tapped in easily because they understand our values and expectations. These consultants have other priorities, but I2I is a major part of their consulting portfolio
(3) Integrated consultants who work across several I2I projects at once and are committed to growing I2I together.
We are in the process of transitioning our integrated consultants to full-time employees, which requires ensuring our finances and HR systems are in place for long-term stability. This is a major focus of 2023. Eventually, we’ll mostly rely on FTEs rather than contractors, but we are taking our time to scale sustainably.
In January 2022, we hired an assistant, Maria, and she has been a major asset to our team! We found her via Peachtree VA – a company for small businesses like ours to share virtual assistants. I first realized I needed to hire an assistant when too many things were falling through the cracks. I was tired of responding to emails “in my head,” forgetting to send calendar invites, and letting bright ideas die on the back burner.
At first, I felt guilty about hiring an assistant. I thought I wasn’t “important enough” to have one. Then, I realized that doing everything by myself (and failing at it) signaled that I2I wasn’t “important enough” to invest in the right support systems to succeed. In fact, administrative tasks are just as important for the success of our small business as our project work and business development.
STEPHANIE
All growth comes with some growing pains. Can you share one pain and one unexpected win?
NINA
Here’s one pain AND win: We are turning down opportunities because we do not have the bandwidth to take on more projects.
(It’s just Stephanie, talking to you Dear Reader, from here forward.) That kind of growth in just a few years is only possible when you have a team.
I remember making my first hire – it took me years to figure out the confidence, the logistics. But once I did, I wished I’d have made my first hire sooner. Matter of fact, every entrepreneur I talk to says the same thing.
In the conversation above, I bolded Nina’s comments that reflected critical decision points that led to growth. While everyone’s path is different, I hope you’ll begin to recognize when you’re having similar thoughts and identify those as signs that you’re sprouting beyond the terracotta you’re currently in.
PS. Nina’s also a guest speaker inside Boost & Bloom!