Bosses vs Teammates

People will work hard to avoid disappointing their boss, but they will do almost anything to avoid disappointing their teammates.

If you’re a leader, figure out how to help your team trust and hold each other accountable. It’s far more effective and fun.

Something I’ve learned though: I don’t get to have an arms length involvement. As the leader I need to be in the thick of it with the team, too.

When It’s Time To Replace It

A growing organization must evolve. The requirements we followed yesterday may not meet the demands of today. Generation 1.0 can sometimes support our needs by improving to 1.1 and 1.2, but at some point we outgrow our existing (infrastructure, org structure, people, systems, processes); then it’s time to move to 2.0.

I’m learning I have the most fun working with people who work hard and play fair, and also have the humility and awareness to be willing to set aside what we proudly built yesterday and replace it.

The Hard Work of the Leader

The team is perpetually trapped in the whirlwind of activities that are required to keep the business going. Customers must be responded to. Invoices must be paid or sent. Requirements must be written, communications created, broken stuff fixed or replaced. Work has to get done just to hold the business together in its current state.

To move forward, responsibility falls to leaders to help the team focus. The whirlwind is always present, so only a percentage of time is available for the strategic work that advances things. There will always be more good ideas than there is capacity to execute. Pushing forward on too many initiatives means they’ll all be done poorly. To advance, the organization must focus on one or two things and do them very well. That is the hard work of the leader. To choose.

Good leaders choose a direction and communicate clearly with the team, in the midst of the whirlwind, despite uncertainty.

Changing Seasons

Today I accepted a job offer. After four months of what some jealously dubbed my ‘life of leisure’, I’m headed back into the working world. I feel many mixed emotions, in part from agreeing to shoulder a new set of responsibilities. Laying down the burden of responsibility for multiple months created a special space – a space I’ve coveted – for other mental activity and rebuilding emotional resilience. I also grieve the loss of freedom now that my schedule won’t be entirely under my control. These past months I embraced the gift of time. I traveled out of state, completed home projects that required more than an hour or two, trained for and completed a triathlon, hiked a piece of the Colorado Trail, played a lot of music, did some volunteering. I’ve had more quality time with my daughter in four months than perhaps the entire previous year. When my son calls home from college I can pick up and chat with him, even if it’s the middle of a workday. I’ve been able to hike and bike in the beautiful Boulder mountains, avoiding the much more crowded weekends. Perhaps most potently, I’ve had time to simply relax, to sit, to journal, to meditate, to daydream, be bored, be alone, breathe. It’s been a period for my mind to disengage – not to stop or to take a vacation, but to soften and reconnect with the activities that are my unique blend of healthy mindfulness.

I will miss this time, but two truths are buoying my spirits.

First: I’ve observed there are seasons to our lives. As summer flows into autumn and autumn into winter, so do we flow from one chapter to the next. We live in a great river of change, and every day we’re given a choice: we can relax and float in the direction that the water flows, or we can swim hard against it. If we resist the river, we feel rankled and tired as we tread water, stuck in the same place. But if we relax and float with the river, the energy of a thousand mountain streams is with us, filling our hearts with courage and enthusiasm, even when we turn headfirst into the rapids.

Second: with seasons come cycles. I believe this is not the last time I will live a ‘life of leisure’. In fact, I negotiated and built in those expectations with my new employer – that they will get the best of me and I will help them accomplish a very big vision over the next 12-18 months, and once that mission is complete I will likely leave the company.

The world is filled with opportunity, and this particular job is not an opportunity I thought I wanted. I was (and in fact I still am) leaning heavily toward a future in which I serve clients as an independent. Call it consulting or contracting or fractional, but the work of an independent can touch many lives because it isn’t confined to a single company. And it offers the flexibility of lifestyle that I most desire. I am heading that direction.

So why take a full-time job if I want to be independent? Here is where the mystery and magic of the Universe humbles me. To be successful I’ll need a pipeline of potential clients. I don’t have that today and I’m starting from scratch. Building and maintaining pipeline requires investment and time. If I start today, it will take many month to build a client list, and during that time I need to resume an income, so I will inevitably take clients out of desperation that may not be a good fit for me.

Taking a new job, especially one that has a fixed time horizon, is an unbelievable benefit. This season of my professional life will sustain me financially, challenge me intellectually, and perhaps allow me to fill out some skill sets, all while I build a consulting network and pipeline that I can lean into in the future. This next chapter isn’t just about the job, it’s about the collection of activities across my life – within the job and outside the job.

One last thought before I close this post. As I mentioned I wasn’t looking for a job. This one landed in my lap very unexpectedly. The universe presented it, and each step of the process has been surprisingly frictionless. Everything has just flowed, from the interviews to the proposal I presented, to the salary and negotiation process. Where other opportunities in the past four months met resistance or unresponsiveness or other difficulties, this opportunity was like following a route where the lights are all green. I want to trust that. I choose to trust that. I trust that moving in this direction where life just seems to flow, where the green lights lead, is in fact the right direction. Perhaps for reasons I cannot see right now.

Inside my mind, I confess feelings of fear, uncertainty and doubt because my personal preferences don’t want to give up the freedom I’ve enjoyed for the past four months, yet I choose to trust this forward motion will continue to lead me on the path toward rapture.

A Timely Reminder

This morning’s daily post from Seth Godin is called Without Reservations. Here’s an excerpt:

“Yes” can mean, “yes, I’m prepared to do the minimum” or it could mean, “yes, this commitment is something I wholeheartedly embrace and will devote myself to exceeding expectations at every turn.”

Life’s way better if we find partnerships that are the second kind.

This message was perfect timing for me. I’m deliberating a lucrative job opportunity that may require a soul-sucking commute. I realized I’ve been evaluating whether I’m “prepared to do the minimum” which of course will only set me up for misery. After reading Godin’s post, I’m reframing to evaluate whether I can commit to this wholeheartedly. If so then the commute won’t even factor in because I’m so excited about the work, the people, the impact, and what we can build together.

The latter will lead to opportunities for rapture: being all-in, being fully present with the people and problems we’re solving, becoming vulnerable to others who are also all-in on the same mission, and living a life wide open.

Being a Winner Is…

They say that winners have mastered good habits like waking up early, reading, exercising, meditating, creating multiple revenue streams, staying disciplined, and blah blah blah. You’ve read these types of lists hundreds of times. However, the real way to be a winner is to decide what you want out of life, how your business or career can contribute towards your overall purpose and goal, and to then march forward. Some of the cliché habits above may end up being part of your keys to success, but just going through the motions doesn’t do anything if you don’t know what you’re going after. Winners know what they want and are living accordingly.

Keep It Light

Keep it light. Whatever is happening, it’s really not that important.

Making it heavy makes it heavy for everyone. Heavy sighs. Heavy words. Heavy thoughts and heavy heart. No question that those emotions are real, and the hardships of life are real; and we need to shoulder them bravely; and we should ask for help when we need it; and help others when they need it. But no need to overdo it. Overdoing it is just a way to get attention for ourselves, or feed our ego subconsciously. Heavy sighs and heavy words put more on the people around us. They have enough already.

In the grand scheme of the Universe, whatever we’re about to complain about just really isn’t that big of a deal. Whether it goes the way we want it to, or not, a hundred years from now it won’t even be a whit of a memory in anyone’s mind.

Keep it light.

Past 7 Days

I recently re-read an old post The Rapture of Being Alive and decided to capture moments of rapture from the past week. For me, experiences of rapture are more than just feel-good moments – they are experiences that open us up, they invite vulnerability, and they make us more freely available to others.

From the past 7 days…

I felt it with Michelle yesterday, as we got deep into conversation about kids and sports and cell phones and growing up.

I felt it Thursday on the Boulder Skyline Traverse hiking with Bart Foster and 40 other amazing business leaders / outdoor adventurists.

I felt it when I texted Dad about the Chaos Walking movie.

I felt it last weekend when Joe and Jack and I were climbing in Boulder Canyon.

I felt it with Quinn at the coffee shop this week, talking about the photography on the walls.

I felt it with Luca this morning, hiking up to the Royal Arch in Boulder, discussing career and friendship and spooky tales of haunted houses.

I felt it last week at lunch with the CFO/COO of the Colorado Mountain Club. Jacob shared some inspiring mountaineering stories, interspersed with business challenges they’re tackling at CMC.

I even felt it playing fetch with the dog, and tug-of-war with a rag.

These are older than 7 days…

I feel it on every exec hike with Geoff.

I feel it every time the Zen Mustache crew takes the stage for a performance. And any time we get together to play music, even if it’s just in the garage.

I felt it riding my bike on paths through the nature preserves south of Chicago.

I felt it camping by myself in the back of the truck, listening to insects chirping and the wind in the forest.

I felt it visiting the Field of Dreams in Iowa.

I felt it laying flooring at my parent’s house, crawling around on my knees, moving appliances, and listening to country music.

Looking at the list above, trying to extract what’s in common. It’s not about the specific activity. Seems that rapture comes from two places:

  • It’s about who I’m with and the openness of that relationship, or:
  • It’s about being open to the moment at hand and immersing completely in the experience – not worried about other things – so the focus is completely present.

Those are moments of rapture, and it turns out they are everywhere.


My son, a college sophomore who is deeply entrenched in STEM classes this semester, called last week feeling overwhelmed. He had just finished the first part of a two-part physics exam, and felt crappy because he’d left 2 out of 4 questions completely blank, and wasn’t confident on the two he did answer. The second half was coming tomorrow, and he had so much studying to do; he just wasn’t getting the concepts. But he also had calculus homework due the next day (mostly completed over the weekend, but needed to be finished off), a computer science assignment due the following day, and some drawings for his technical drawing class. That was all just in the next two days. Plus his hourly work at the events center, practicing his music for weekly lessons, and his climbing team commitments. Somehow this was only week 4 of the semester. He was asking me, rhetorically, how he would ever be able to keep up?

Here was a perfect moment to lay on the wisdom, to bring my years of life experience into focus. Surely I could craft some insightful advice that would help my son in his moment of despair.

“That’s so hard. I’m so sorry you have to deal with this.”

That was basically the gist of my message. Yep, the editors of Parenting Magazine will be calling me any day now.

My son mentioned during our conversation that he wanted to find the right work life balance. That he had seen me working so hard and being terribly unhappy (prior to me finally making a peaceful transition out of my start-up company), and he knew he didn’t want that for himself. But he did want to work hard enough to feel good about his work, and he did want to build a responsible life for himself.

At one point during the conversation I told him something along the lines, “College is a different season of life than anything else you’ll have when you’re in the work force. College isn’t about work-life balance, it’s about work-work balance.” He laughed and said, Yeah it’s not about whether or not to get it done, it’s only about when and how to squeeze it all in, and with what level of effort.

This HBR article reinforces something many of us have already instilled in our lives: making time to recharge. It’s more than unplugging, or breaking the routine. Both the body and the brain need recovery time. Not just rest, but recovery. I’ve been out of the workforce for a little over two months, and I’m just beginning to feel recovered.

Reading this article makes me think it’s not about work-life balance, it’s about engaging in work that is meaningful to ourselves, and then doing things that truly recharge. In that model, we don’t really have an opportunity to burn out.

My Changing Role as an Ops Leader

My function as a operations leader at Nextbite is changing. When we were 10 people, I was involved in everything. When we grew to 35 people, I had leaders managing day-to-day but I was still involved in every project. Now that we are well over 100 people, what the organization needs from me is changing again. I’m writing this down to capture my thoughts at this point in time, and in the future I can look back and see if I was right or wrong (because honestly, I’m making this up as I go).

I recently brought on a General Manager of Operations. Three or four months ago, one of my executive colleagues convinced me I needed help because the Operations team was just so huge. We started a hiring process and our new General Manager started about 3 weeks ago. She has a very strong personality and is taking the org by storm, coming up to speed quickly and earning a reputation as a progressive-thinking go-getter.

As she takes the reins overseeing day-to-day operational concerns, I find myself in a new position. I will no longer be in the weeds every moment, and someone else is looking after the day-to-day. So what will be my focus? Here’s what I have so far:


I want clear visibility into every team’s objectives for the quarter, and I want to be able to see their progress to date at any given time. We have several good systems in place today (we’re using the eOS framework) but I’m not convinced everyone knows their team’s mission for the quarter.

I also want clear visibility into any project the teams are working on. Our company uses Notion to capture and share information and some of our team members are amazingly diligent. It’s so easy to quickly understand that state of a project, what decisions have been made and what is the trajectory of the work. I need to make these individuals into role models and duplicate their excellence throughout the org.

At the start of every quarter we re-up our department-level goals, and all teams need to update their projects and targets accordingly. I need to be clear about the ‘why’ especially as priorities shift from one quarter to the next.

Once everyone knows what they’re working on and why, I need to be a cheerleader. Encouraging, nudging, helping leaders hold their teams accountable, removing obstacles, and celebrating every victory that I observe. The more I observe, the better, because when people see that I’m paying attention, and that I want to celebrate their wins, this will be a positive motivator in the culture.


Not just to my new General Manager and the one or two other leaders who report directly to me, but to everyone in Operations. This means making myself available to front-line teams, learning what they do and how they do it, asking questions and confronting/challenging/encouraging/nurturing.

Two two greatest characteristics I can embody as I go about these conversations: Empathy and Perspective.

Empathy (not sympathy) that I understand how hard the work is and I’m willing to jump into the bunkers with team members and experience what they’re going through.

Perspective, so each person understands that what they do matters and how their work connects to what the company is trying to accomplish. For our younger workers, who are being managed by younger managers, I suspect there will also be opportunities to share perspective about each individual’s professional experiences and growth.


The org will be so heads-down and it’ll just keep churning on a process that might be not be working efficiently. It’s up to me (along with the GM) to spot areas where things could be breaking, or there might be a better way. This means talking to teams and listening for their frustrations. It means connecting with people in other companies and learning how they do it. I could also mean learning about new tools, processes or best practices that may be available.

Okay, those are the 3 big areas I’ve identified as I redefine my job. There will be other things I need to do, too, like keeping a thumb on what our competition is doing, working with Product & Engineering to determine the right technology strategy, working with Business Dev to bring home whale accounts, etc. But on the question of how do I support the Ops teams and create an environment where every person can be the best version of themselves at work – that’s where my head is today.

Opportunities to Engage

We should never get complacent about opportunities to give praise/be grateful/be engaged to all of our hardworking people & teams. Whether directly to those that deserve it, or publicly in front of a group setting, it means so much to our employees to hear from their leaders.

“Hey, that update that you sent was very clear and concise, and I really appreciate how you always communicate the challenges that are on your mind.”

“Thanks for being brave and offering to role play with us to create a better process for selling.”

It’s also good to ask follow-up questions to communications (shows great engagement) like, “Thanks so much for sending these 3 product updates, I noticed there wasn’t any mention of project X, are we still on track?”

I encourage every leader to be engaged, ask questions, give feedback, and sing praises more often.

Keeping cameras turned on during group zoom meetings helps too (even though it can be exhausting sometimes).

Reach out to someone on slack that you haven’t spoken to in a while, and just say, “Hey, how are you. It’s been too long. Just wanted to check in to say hello.”

Or if there is someone new on your team, message them saying, “Hi there, I wanted to check in now that you’ve been here for a couple weeks. How was the first few weeks for you? Is there anything that’s been hard or confusing?”

This doesn’t just apply to direct reports, but even newer junior people on our teams.

I realize this is tough when we have our own jobs as leaders. The more engaged we are, the more connected our team members will feel.