Leading during uncertainty

“When you are in a dark place, you tend to think that you were buried, perhaps instead you are being planted.”

Dr. César A. Cruz

Carrots, eggs, or coffee. I adore these metaphors as a way to help frame a spectrum of when I experience uncertainty, stress, or constraints. As I continue my journey towards a growth mindset, I remind myself that the journey is the destination. And I also must remind myself that others are on their own journey, at their own pace. 

Wherever you are on your journey, here are a few resources that I’ve found impactful.

Self Awareness

Yes, it is okay to experience grief and sadness. 

Yes, it is okay to experience laughter and joy. 

Yes, it is okay to experience all the emotions in the rainbow. 

Staying with emotions, I recently watched the powerful documentary “The Mask You Live In” and its message resonated deeply with me. It took me years to realize how my behaviors were connected to the emotions I was experiencing yet not acknowledging. I worked with a cognitive behavioral therapist for years to assist with retraining my neural pathways. Everyday I work on my self awareness, yes it’s a skill, of my emotional wellness and my physical wellness.

Mental Wellness

Dear self, I love you. I adore Dr. Cesar Cruz. Here is a love letter he wrote to his own mental health and his guided meditation.

MIT hosted an amazing conversation with Arlan Hamilton, Brad Feld, and Kathleen Stetson about the importance of mental health. 

I believe we are in the moment where we can openly discuss our mental wellness journey and find support systems to buoy our efforts. Every colleague, coworker, or employee is a human with their own journey we can acknowledge or dismiss. I choose to acknowledge.


The difference between empathy and sympathy is wonderfully articulated by Brene Brown. She also does an amazing job distinguishing shame and guilt

Recently Josh Bersin published an amazing article about leaning into our human skills during times of uncertainty. 

Time and again you will hear: “Humans do business with other Humans.” Yes, you may have a B2B or B2B4C method to make money. However, organizations are simply a collection of humans. Make a human decision.


For a long time, I blamed my brain for causing my behaviors. I undermined my own intelligence and competence, cue imposter syndrome. My neural pathways were so ingrained that I believed my thoughts. Fortunately, I discovered neuroscience as it applies to leadership and Dr. David Rock’s work in this space. 

Several amazing suggestions provided in this webinar recently launched: Neuroscience What Science Says Leaders Should Do in times of crisis.

Learning Zone

First, reflect on where you stand in the spectrum. Comfort Zone / Fear Zone / Learning Zone / Growth Zone. Address your own needs. Then, as we interact with friends, family, and colleagues actively listen for words and phrases that indicate where on the spectrum they are. Listen to tone of voice, watch for eye contact, and any shifts in what you previously experienced with this person. 

If you have the capacity, how can you help create space for folks to move through each zone? Some fantastic tips in this article about psychological safety.

Self Care

Summarizing these points together, put on your own oxygen mask before helping others. Care for yourself before trying to serve others. I encourage you, please prioritize your wellness – nourish yourself with water, sunshine, and fresh air – so that you can continue to be of service to others. 

If you find yourself at a grinding halt or overcome with grief, self care. I did. Then slowly, intentionally find sunshine, literally or figuratively, to help keep moving forward step by step. Find ways to create new routines and methods to interact with friends, family, and mentors. Remember to prioritize your own self care. Nourish yourself.

Self care is not selfish.

Be well, find laughter, protect your immune system, and wash your hands.

First 20 days of 2020

I helped run a two week bootcamp in Cape Town, South Africa where we nurtured entrepreneurs solving social impact problems in the local market. Hope your 2020 is off to an amazing start!

BonBillo Bootcamp

BonBillo brought a cohort of 8 ventures through a structured curriculum and helped them define the venture’s theory of change. As one participant said, “bootcamp is like bringing your business to school.” Our team of 3 complementary skill sets helped spark new ideas, new ways of thinking, and new perspectives to their venture. Most rewarding is to see the delta each entrepreneur experienced as they grew. 

BonBillo partnered with two amazing organizations locally. Startupbootcamp Afritech for guidance navigating the local startup ecosystem and VACorps for memorable excursions and experiences. Our teams received a lovely feature in a local venture publication; let me know if you’d like to learn more about our teams. 

In lieu of traditional New Year resolutions, I’m settling into the pathways I’ve been forging. Deepening my commitment to my art, my startups, my students, and myself. Grateful for the opportunities to nurture the next generation of founders, entrepreneurs, and CEOs. Grateful for the amazingly talented individuals in my universe. Grateful that you are part of my journey. 

Journeys are never linear

I launched my first class teaching with an epic technology fail. We swiftly recovered with a pre-recorded video; embarrassingly evocative of Office Space, complete with a ficus tree in the background. I’m highly confident the video will not go viral; please don’t bribe my Teaching Assistant. 

I did share with my students learning is an emotional process. Growth is always emotional. All emotions are valid. I am highly confident I will have additional epic failures during my journey as an instructor. However, I genuinely interpret “epic failures” with an orientation towards a Growth Mindset. 

I am also an epic planner. It’s one of my superpowers. Planning a directional journey helps you realize when you need to course-correct. Not the planning-every-last-detail-micro-manager type. The type of introverted planner that deeply cogitates and then coordinates. Say for example, what would happen if our journey led us to trip and fall into a deep canyon like our stick figure friend in the illustration. 

We can either wallow at the bottom of the canyon because we failed. Or we can evaluate our inventory of food, water, and supplies in our rucksack. Look to the people supporting our journey. Evaluate the canyon walls. Make a determination of rock climbing the ledge or signaling to people for help. Growth is always emotional. All emotions are valid.

How can I help your journey?

How to create a culture that attracts top talent – panel recap

Grateful for the opportunity to help the next generation of leaders, entrepreneurs, and go-getters! I spoke on a panel during Startup Boston Week. Aubrie did a phenomenal job moderating a panel with brilliant colleagues: Melissa, Kevin, and Lori. 

I mentioned a couple resources and wanted to summarize here:

  • Bring your whole self to work. Adore the culture blog by Motley Fool. I’m especially cautious that bring your whole self to work does not mean bring-your-bag-of-drama-to-work day 🙂 We are humans going through this journey and it is important to extend compassion in the workplace. 
  • Hiring takes hustle. There are no silver bullets to hiring the “perfect” candidate. Colleague. Every resume is a potential colleague who will add tremendous value to your startup. See the possibilities, be self aware of the startup’s current business stage, and ask meaningful questions.
  • Trust Gap. Understanding how each individual trusts and what they need to bridge the trust gap is incredibly powerful. Some folks automatically trust a person they meet for the first time. Other folks need you to earn their trust. It’s a spectrum, not binary. 
  • Timing & Peak Performance. Understand when you are most productive, energetic, and resourceful. Plan your day around you! Be mindful that your colleague’s most productive time might be opposite of you. Work is no longer 9 to 5. Butts in seats does not equal productivity. 

Good luck to all the participants in the session! Have a great time during Startup Boston Week! 

Need more inspiration? I regularly curate articles to my Pinterest board, follow along!

What are you waiting for?

Often times our people strategy lags behind the business strategy. You know a business strategy includes building the product, securing funding, and proving our go to market concept. People are resources we hire and delegate responsibility. But what happens when we grow so fast that we overlook our people strategy?

The expense of not having a people strategy is often unreported – lack of trust, turnover, disengagement, etc. All of these impact your business strategy. How many headlines have you read about ousted CEOs, claims of harassment, or back channel murmurs?

So what are you waiting for?

Let’s get started!