© Rahshia Sawyer 2021

2021 — Leading through the last mile

Rahshia Sawyer
8 min readJan 11, 2021


Everything I did in 2020 felt bass-ackwards; The playbook for Leading Through Chaos v0.1.

I view leadership as a verb, not a position. It’s the actions we take as we lead ourselves, our colleagues, our teams, and our organizations — you, my friend, are a leader. And as a leader, I never found the chaos playbook, a guide to leading in 2020.

I can attest that it was a brutal year, both professionally and personally. The chaos of the global pandemic, anti-racism protests, and political turmoil riddled the months with relentless compounding challenges. What worked in 2019 did not, no-way-no-how, work in 2020.

As we enter 2021, I want to call out that we’re in the last mile.

The last mile is often used to describe the final stage to deliver a service, historically used in telecommunications when network-lines were needed to physically reach a user’s home. It’s commonly used as a metaphor to describe the last part of an experience — usually, the hardest.

In 2020 we were physically disconnected and yet continually digitally connected. Work-life boundaries blurred, creating a new space in which to function, full of ever-changing nuances. As we wait for the vaccine to arrive, we will continue to work — from home in hyper-digitally connected environments — we will be together but separate.

Whether we realize it or not, 2020 was a masterclass in Resilience. The ability to bounce back, overcome obstacles, and recover in the face of unrelenting challenges while balancing between competing constraints. And when things get chaotic, when it feels like everything has gone off the rails, I instinctively reach for a playbook. A guide with all the pieces and parts, actionable plays, and strategies to bounce back. A reminder of principles, methods, and tools to true back to. For 2021, here are four additions to add to your playbook:

  1. Ambiguity is the enemy of certainty,
  2. Limited choice relieves anxiety,
  3. Right sized-challenges inspire us,
  4. 2021 is the year to delight!

We’re going to need all of them and everything we learned in 2020 as we navigate into 2021, and yes, the last mile will have its chaotic challenges.

First, a nod to what we lost.

We lost certainty and novelty. The assurance of our daily routines changed. Our senses went into overdrive, depleting our attention spans, leaving us in a constant state of addled brain-fog, and raising our anxiety to unprecedented levels. The lines between work and home blurred, forcing us to be vulnerable in new ways. And along with our certainty, we lost novelty. Novelties that allowed us to perceive the passing of time. The chance encounters, the hallway run-ins, casual coffee-line conversations, and that organic collaborative quality in our work. These things added an element of unexpected novel delight to the day. Experiences that made us feel that we belong.

But 2020 was not without its blessings. I’ll admit that sentence was hard to write; I don’t think I have ever cried as much as I did in 2020. And yet, through all the chaos (and tears), we now have the luxury of hindsight to find silver linings.

What we gained from 2020.

We gained a genuine human connection. We connected through digital programs where we brought a different type of humanity, a more accepting one. We connected with others by actively listening. By being vulnerable and uncomfortable; by staying in hard, difficult conversations, the type of conversations that stick with you. We shared our humanity, leaning on one another. We held space for each other’s raw and heartwarming humanity. We were there for each other. The pretense of having it all together dissolved as we faced the most chaotic year of our lives — together but separate. Maybe we were just reminded of how important connection is.

We also connected with ourselves. We were forced to stop our daily grind, giving us time to assess what mattered. Time to re-connect to ourselves — to listen from within. To rediscover things that we once loved, things that give us energy, to explore new passions, and to rest — everything we will need for the last mile.

We’re not out of the woods — yet.

We’re still depleted from 2020. We’ll need to be careful not to think we have this all figured out. As we’re still physically disconnected in a blurry, almost on-the-other-side-of-this liminal space, without any timeline as the last mile will be longer than a month — or a year.

Our lives are still without control; we’re just getting used to it.

We need to continue to meet people where they are at and be serious about mental health. The last mile can be the hardest. Feelings are still unpredictable, fine one minute and not the next. I assert that no one is fine. We brought hard societal topics into work conversations; we now need to normalize talking about mental health as work may be the only place where somebody will see us. It will be hard to tell who may need a pick-me-up, some relief, or space. The unrelenting stress affects all of us; I don’t think anyone is escaping the pressures we’re still facing. To continue our genuine human connection will require us to be vulnerable first, be curious, and offer our time. We’ll need to ask different questions:

  • “I’m having a hard time with [blank] and focusing on [blank]; how about you?”
  • What are you feeling?”
  • “I’m going to watch/do [blank], want to join me?”
  • “I’m curious, what is helping you right now?”
  • “Have you gotten into any good books/TV this week?”

We need to stay genuinely connected for our team’s mental health, so we can intervene sooner rather than later through actively listening — even in the hard, uncomfortable moments. As leaders, we need to engage everyone where they are at.

The playbook — Leading Through Chaos v0.1.

We did not have answers for the collective challenges we were facing in 2020. And as we understand the impacts of sustained stress and learning how to function, we’ll need to continue to do things differently — just a little bit longer. Here is my playbook to help energize and create the space to overcome the challenges we will face in the last mile.

Ambiguity is the enemy of certainty.

Nothing will stop a project in its tracks like ambiguity. It triggers our threat response resulting in more anxiety and continuous overwhelm. Also, people are less likely to be engaged with vague information. Coupled with prolonged stress, our ability to break down ambiguous problems is hindered — till teams are back in high-performance mode:

  1. Give more information by adding context to project goals, detailing out outcomes, or simply putting your brain on a loudspeaker in a weekly recap writeup.
  2. Define clear-er smaller goals. Climbing Mt. Everest can still be your goal; focus on near-term outcomes vs. getting to the top of the mountain.
  3. Focus on shorter timeframes, a quarter vs. the annual OKRs. Right now, in the last mile, 14 weeks will feel like a year.
  4. Set the bar and don’t raise it; this will be tough for high performing teams, but we can raise the bar at the end of this.
  5. When things go off the rails, ask, “What can we do right now to pull together to get through this?” The last nine months have already proven we will get through this together; focus on just this problem (not all the problems).

Limited choice relieves anxiety.

Our instinct to be in control will go into overdrive in times of uncertainty. Research has shown that when people feel autonomous (free to choose), it lowers their anxieties as they feel more confident, satisfying their need to be in control. However, in chaos, we’re overwhelmed, hindering our ability to be decisive, plan, and prioritize, making even the most manageable choice hard. Providing limited options will simultaneously offer control and lower anxieties — when anxieties are running high and people need space, try these approaches:

  1. Ask the team to come up with the “how” to solve project goals.
  2. Instead of outlining timelines and due dates, ask, “When can this be done?” or “What can you get done by X?”
  3. Set up different meeting formats; video, audio-only, and chat. Not everything needs to be over video or in real-time.
  4. Share information synchronous AND asynchronous, giving people space (and choice) to consume information at their pace.
  5. Have a variety of pulse-checks from asking, “What is the feeling right now, in this meeting?” to a weekly group message for everyone to share their Rose (a highlight), Thorn (a challenge), Bud (a new idea).

Right-sized-challenges inspire us.

Challenges, especially ones that strike a balance between total overwhelm and feeling endless, inspire us. For the last mile, the are-we-there-yet mile, it will feel endless. Inspiration and patience will be in short supply. Our focus will be pulled to basic physiological and safety needs, the things that feel urgent, putting any long-term strategy in the back seat. Shift the teams focus on what will be needed when this is over by:

  1. Identify bigger challenges than what feels physiological urgent at the moment.
  2. Remind the team that they are, in fact, good enough and can solve this problem.
  3. Create a source of truth. Project goals, decisions made, timelines, updates, assets, etc. It’s still hard to remember from one day to the next. We’re all remote, so a shared digital space (hopefully) is easier to maintain.
  4. Recognize successes and progress (even the small victories) to build back confidence.
  5. Be consistent in your actions and structures with weekly, monthly, and quarterly rituals for your team.

2021 is the year to delight!

Surprises are so 2019. Studies have proven that people remember small and unexpected things. From a good morning Slack message to a handwritten card from your boss, these unexpected things delight us — giving us a (needed) energy boost.

  1. Meet new colleagues and grow your team’s network by inviting colleagues to informal coffee chats. You might be surprised how many people will jump at your invitation. It’s a win-win-win for delight.
  2. Organize cross-team events to encourage free-thinking, adding some organic collaborative quality back into our work.
  3. Challenge the team to experiment with new ways of working. See “Set up different meeting formats” for some thought starters.
  4. Spin up a virtual Appreciation prize wheel, where teams can submit about other team members they appreciate — and why. Once a month, spin the wheel a few times and whoever it lands on gets to choose from a pool of intriguing prizes. Choice and delight, that is a winning combo!
  5. Piquing curiosity is a delightful way to help teams stay engaged. Done well, it can interest people to stay engaged to find out what is on the other side.

The last mile has started. As we lead ourselves, our colleagues, our teams, and our organizations through the hardest part, the last part, remember we will be physically connected again.


Nothing happens in a vacuum; this article would not have been possible without the leadership of others. The experience design leaders, researchers, journalists, and colleagues took the time to connect and share. Thank you, Brandon Schauer, Kim Rees, and Nancy Dickenson. Thank you, Tara Haelle, Dr. Merete Wedell-Wedellsborg, Tiphani Palmer, and Harris III. Thank you, Dorothy Levin, Lisa Gironda, and Jessica Saia. And thank you to all the fellow creatives who were vulnerable.



Rahshia Sawyer

Rahshia Sawyer is a creative professional and third-culture individual based in the Washington DC area.