How to keep your sanity during a crisis at your start up

Anna Talerico
Jan 9, 2018 · 8 min read

This is a story about a time when, in our 50-person company, I had a VP and a director out on maternity at the same time, and then had another director quit, leaving me down three key people at once. This article isn’t about how I managed my to do lists or how I shuffled responsibilities to cope. This is about how I preserved my sanity.

To be fair, when running a bootstrapped marketing technology company there is almost always some type of organizational strain and there are plenty of periods of significant stress. Ok, there is significant stress—all. the. time.

But this was a particularly unique situation and I really braced myself for impact. The preparation helped our company, and me, come out the other side much stronger.

Our company was about $10 million in annual revenue, 50ish employees and 200 customers. I had a VP of account services who led three departments, totaling 20-people. I was personally leading the sales organization, with about seven direct reports, and one team leader who was running a subset of the sales team.

With me so far? In a nutshell: we were small, lean and trying to accomplish a lot in a highly competitive market.

Things across my departments were fairly manageable (as manageable as a growing marketing technology company could be) and we were in a groove.

One morning in the late spring my VP and I were at an off-site planning meeting when she gave me some very exciting (and very welcome) news: she had a baby on the way with a due date of the following February. She and I were close, so I knew that this announcement was imminent. I was thrilled for her. On the work front, she and I felt ready — her team was strong and capable, and we knew we would hardly miss a beat during her upcoming maternity leave. We had been preparing for this moment.

So far so good. Right?

About two weeks later, she called me into a back conference room in the middle of the day.

“I have great news” she said with a smile. “Our director of creative services is having a baby!” Then, her smile grew weaker as she said, “She’s due about two weeks before I am.”

My initial reaction was very genuine excitement. In a small organization women can be hesitant to share the news of their pregnancy, knowing their teammates will probably need to handle an increased workload during their maternity leave. Because of this, I made it a personal policy to welcome every new maternity announcement only with pure elation (no matter how scared I may have felt on the inside!). Pregnancy is just a fact of life, and the work aspects can always be navigated around no matter the size of the company and team. I wanted moms-to-be to feel supported and my first initial reaction was an important part of setting the right tone.

After my first “pure elation” reaction, my next reaction was “Hmmm, well this is a bit of a pickle, timing wise.”

Scratch that. Actually my next reaction was, “How in the eff are we going to get through three months without them both?”

And then some tears alone in the janitor’s closet. Really. Selfish tears.

They were both key, high performers who shouldered a lot of responsibility and were a big part of fueling our growth.

My VP account services’ maternity leave would be felt, no matter what we did. But we had a plan, and it involved relying heavily on her three directors to fill the gap with me at the helm. Now, with one of those directors out at the same time, we would need to regroup and make a new plan. Which we did. We shifted the director responsibilities across the remaining two directors and me, and the three of us together would hold down the fort.

To be honest, I really did cry a few times that winter. And I am not really the crying type. Thinking ahead to what February might be like without these two key team members made my lip quiver. I knew we could get through it, I just was uncertain as to the impact to me personally.

My concern was entirely self centered. I knew the company, and the customers, would be fine. That’s all that really mattered. But I anticipated many ‘all-nighter’ type evenings and fielding lots of day-to-day issues that I had not personally handled in a long while. Would I be able to get back in the saddle of the front lines? What if I screwed up this well-oiled organization? What if I dropped major balls? I imagined the stress of trying to keep the wheels on and the pedal down, and I was worried. I was already stressed, how was I going to handle even more stress? I had never really doubted my capability at work until then.

As the months leading up to what I started referring to “our double maternity” whizzed by, I stopped the lip quivering and instead I started to consider my own personal ‘maternity’ plan.

How would I navigate the new, added demands on my time, when I was already double booked, constantly pulled in a million directions and overtaxed with my own responsibilities? I knew I couldn’t wing it, and I needed to really think through how I could navigate this time successfully for the company, without losing my sanity.

I came up with a plan for personal management to help get me through it — and thank goodness I did, because about one week into our double maternity, one of the remaining two directors quit very unexpectedly for personal reasons. That left me down a VP and two of her directors. Talk about weathering a short-term tsunami of chaos and disruption.

Here’s what I did, and why it made all the difference.

  • I started to mediate. Everyday. Without fail. No matter how crunched for time I was. I had tried meditation a handful of times before and I was neither a skeptic or a convert, I was neutral. But for some reason, I decided that during the double maternity I would find 10 minutes a day to meditate, every day, no matter what. Normally, this is the kind of decision I would make that would quickly fall by the wayside. But I stuck with it. I think it felt like “do or die” and I just didn’t give myself a choice. I meditated every day with the Headspace app. It helped provide a bit of calm to my day, and is a new habit that stuck with me even after the double maternity was over. Meditation is now a regular part of my life and it does provide me with some peace and clarity. Carving out this time for myself helped me learn that no matter how chaotic things get, there is always a few moments to stop, step back and breathe. This helped me get perspective, separate a bit from the fray we were in, and drastically diminished the overwhelm.
  • I radically reduced decision fatigue. I had read articles about people who (like Steve Jobs and Mark Zuckerberg) wore work uniforms. Something clicked when planning for my double maternity and I went into uniform mode. I wore the same earrings and necklace every day for three months. I wore a white shirt and black pants or jeans, with the same heels, each day. I alternated between the same two restaurants every day for lunch, and ordered the same meal. I shut down decisions, because there was literally no brain cells left to make them. This food/clothing uniform suited me well and I was surprised by how much mental energy it freed up to help focus on what mattered. I can’t say this has stuck with me in such a drastic way since the double maternity is over, but there are remnants. When I get overworked or stressed, I automatically default to minimizing decisions. And in general, I tend to fret less over simple day-to-day decisions. I learned that choice is an energy, time, and focus zapper.
  • I got an executive assistant. Before the double maternity (and unexpected departure of a director), I was already over scheduled and had significant operational/tactical responsibility. In the face of taking on their key responsibilities with one other director, I needed help. While our company didn’t have a culture of using administrative support, I knew I would need an executive assistant to keep my personal ship afloat. How the executive search and subsequent hires went is a topic of a whole other article, but suffice to say, it was a big relief to acknowledge that I was going to need someone to manage my schedule, to do list and personal/professional errands.
  • I made space for others to rise to the occasion. Like many entrepreneurs, I can be a perfectionist, which can lead to micro-managing. My hands are always on everything, to a fault (Hey, I’m working on it!). Managing so much compressed responsibility left a lot of space for others to shine. The manager who was leading a sub-set of the sales team stepped up to take on much more — without me asking. He saw the gaps I was leaving and just naturally filled them. The remaining lone director who was left to manage the double maternity with me tripled (and I do mean tripled) her to do list, daily meetings and responsibilities without breaking a sweat (and I bet she didn’t shed a tear the way I did). Obviously, that workload wasn’t sustainable, but for three months she just switched into hyper drive and it was a beautiful thing to watch. I realized how innately capable she was in a time of great pressure. Two people I now found myself leading came to me with a problem during this time, and ended up being inner circle confidants in helping me solve what was a very tricky organizational issue (that was also entirely unexpected), and proved themselves to be very worthy of my confidence. I learned that necessity creates space for people to naturally soar and it was exciting for me to see people excel at what they were authentically great at. That director? I would go to her in a crisis anytime. That team leader? He catapulted himself to director of the entire sales team in the blink of a three-month eye. Those two team members? I can trust them with literally anything, they are ‘have your back’ kind of people, which is invaluable. The three months I had to let go helped others in the organization soar, and taught me that the company could be better off without my hands on every wheel.

Without these tweaks and life lessons, I think I would have melted down entirely.

The funny thing is, the new habits stuck for good. I meditate everyday, and when I stray from it, I can tell the difference in my outlook, my focus and how wrapped up I can get in pretty meaningless issues. I am still cognizant of decision fatigue and try to limit it. And I am always working on stepping back to let others shine.

Demanding, challenging times at work can provide many rewards. I am grateful to have lived through our double maternity because it taught me so many life lessons!

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by 282,454+ people.

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Anna Talerico

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SaaS sales, customer success & company culture. Also coffee (lots), wine (even more), yoga (not enough), and family (always).

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