First Official Training Hike!

In order to successfully hike the Colorado Trail one segment at a time, I need to start training. True, this project is probably 2 years away but a slow build is the best way to avoid injury. I also need to re-learn the limitations of my body, which is becoming more susceptible to injury every year. Today I began establishing an initial baseline. These are the first batch of stats I will refer to in the future for planning purposes.

For reference, the Trail will require minimally 12-16 miles of hiking / 3,000 ft of elevation gain, with the longer segments being 25-32 miles of hiking / 5,000+ ft of gain. Today’s hike was in Boulder (avg. elevation ~6,000 ft) but the Trail will vary between 5,500-13,300 ft with an average elevation of 10,300 ft.

Summary stats from today: 5.6 miles / 1,090 ft of elevation gain / Total hike time 2 hrs, 10 min / Avg pace 24 min/mile

The route was a loop starting at the South Mesa Trailhead.

I hiked with Quinn’s 11-month old puppy Cricket. I think it was the longest hike of her life so far. Poor puppy is exhausted this afternoon, but she had fun.

Cricket on the trail

Conditions were muddy at lower elevations and snow/ice at higher elevations especially in the shade. Temps were in the low 30’s at 8am. Unfortunately my boots were not as broken in as I thought and I felt my heels chaffing after only 2.5 miles. I thought I had brought some band-aids or moleskin, but there was nothing in my pack. Those tiny items could have saved a lot of discomfort.

I’ve said it before: if you own the right gear or the right tool, but you can’t find it at the moment you need it, you may as well not have it at all. Moleskin or band-aids in my closet at home does me absolutely no good on the trail, and that’s a learning for future hikes. In the meantime, this week I’ll be suffering through a mean blister on both heels.

Nonetheless, Cricket and I had blue skies, warm-ish temps and no wind on this January day. Today’s hike was about 1/3 of the shortest legs of the Colorado Trail. I think my off-the-couch current level of fitness is nowhere close to where it needs to be to tackle this project, but I’m not in terrible shape and it will be fun adding mileage. I will especially enjoy going out to trails that start at higher elevations – probably a lot of exploring the Indian Peaks Wilderness over the coming months and years; something I’ve long wanted to make time for. Assuming I don’t injure my body, this will be a very fun undertaking.

Key learning today:

  1. Cricket is a good trail companion.
  2. Bring more treats / snacks for both of us.
  3. Identify a dedicated backpack specifically for this project, and keep band-aids or moleskin in there permanently.

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.

The Hatching of a Project- Colorado Trail Segments

I have a new idea for a physical and mental challenge to tackle. Finishing the Colorado 14ers in 2015 was a cool moment, and I discovered I’ve missed having that kind of multi-year goal. Others have made a project of Colorado’s 100 highest summits (called the Centennial Peaks of which the 14ers are the first 56 on the list). Or even the 200 highest summits. Or even the highest points in all Colorado counties. Those are cool, but I haven’t felt an inner inspiration for those lists.

Instead, I’m going to hike the Colorado Trail!

The plan I’m hatching does not include a continuous multi-week hike of the Colorado Trail. Instead, I want to tackle it one segment at a time.

The Colorado Trail is 486 miles and travels continuously from Denver to Durango, along or near the continental divide for much of the route, with 89,354 feet of elevation gain. The trail is broken into 28 segments based on where it crosses public roads thus creating trail access. Each segment is between 12-32 miles and 2,000-6,000 of gain.

I want to do a self-supported hike of every segment, and this is going to create some unique logistical challenges. For example, I plan to hike from east to west (Denver to Durango). What happens when I get to the end of a leg? Do I hike back to my truck, doubling my mileage? I’m definitely not up for that.

My idea is to drive ahead the day before and leave my mountain bike and some camping gear at the end of the leg. I can hike the leg one-way, find my stash and camp overnight, then re-stash the camping gear and ride my bike back the other direction.

I need to figure out when I’ll retrieve the camping stash. After I’m done biking? Or maybe just leave it until I tackle the next leg, which could be weeks or even months later.

Also how much total time will I need to complete a leg in this manner? For example if I leave my house in Boulder on a Saturday afternoon, I could drive to the end of the leg (could be 1-3 hours or more depending on the leg), drop off bike + camping gear, then drive around to the start of the leg (could be another 1-2 hours). Then camp at my truck overnight at the trailhead so I can get an early start hiking Sunday morning. Even the shorter legs of 12-16 miles will take me all day, so I’ll camp Sunday night, ride my bike back to the truck Monday morning, and drive back to Boulder Monday afternoon. Seems I’ll need at least a 48-hour window for every leg. Repeat this 28 times, and remember that the further I go the further each leg is from Boulder. That’s a lot of weekends and a lot of driving!

Plus some of the legs are LOOONNNGGGGG like 25-32 miles. Not sure I can hike that far in a day, so is there an option for ultralight backpacker camping? I’ve never done anything like that before, and it scares me a little.

I expect this will project require multiple years to complete. I probably can’t get started until I’ve got more free time than currently available in my life. I don’t want to be away from my kids so this will go into play in 2024 after my youngest finishes high school and heads to college. To accomplish this radical plan, I’ll also need to make some changes in my professional life. Not sure what that looks like yet but current work constraints are not compatible.

That’s all okay because there are clearly a lot of details to figure out in the meantime.

Beyond the overall lifestyle changes that will be necessary, I need to figure out how to train and what to pack. Since I’m planning mainly day trips, It’s great that I can essentially hike with a day pack instead of an overnight pack. That should protect my legs and back from repetitive use injuries carrying heavier loads. But I turn 50 next year and I’ll need to train for back-to-back hiking/mountain biking days.

Many people have hiked and biked the entire length of the Colorado Trail and their blogs and other published resources are filled with rich information. The Colorado Trail Foundation has a great guidebook. I’ll need to buy maps of the areas I’ll be visiting. I think I’ll also want to take a back-country orienteering course; such classes are offered by the Colorado Mountain Club.

The Colorado Trail is not as long as the Appalachian Trail or the Pacific Crest Trail, but it’s close to my home and it will be an epic adventure. I plan to post here as I research, plan and learn. And then continue to post when do it!

Sunday Morning

Scott Adams, who invented the Dilbert comic, mentions this in his book ‘How to Fail at Almost Everything and Still Win Big’ the difference between wishing and deciding.

It’s a key difference, because once we decide, we begin to take action. Wishing tends to start in the mind and stay there.

Deciding involves looking at the cost of pursuing that wish – financial cost, opportunity cost of not doing something else, etc. And then internally agreeing to the cost and moving ahead.

I’ve discovered that 10 minutes early Sunday morning, while the house is asleep and all is still quiet, I can pull out a pen and paper and write down my wishes. Just writing them down makes them feel different. It catalyzes a process that puts thoughts into action and leads to a decision to do – or not do – something that otherwise would float around in my mind.

I find I’m more energized (and happier!) because I’m less frustrated. Despite a demanding career and a busy life I’ve dropped the feeling of dread that life is passing me by. I’m able to put my most important wishes into action because I took time to prioritize and decide.

I don’t think everyone struggles with this. I envy those who do it naturally without much effort. They seem to just know what they want and it’s already prioritized and they’re able to just go. I’m very curious how others manage.

Wild Geese

This poem from Mary Oliver caught me in a moment I was feeling deep anxiety – over work, over life, over whether I’m doing it right.

Tim Ferriss called attention to this in one of his 5-bullet Friday messages, but I only saw it weeks after that particular email came out.

I recognized Mary Oliver‘s name from another poem The Summer Day, particularly a line I stumbled across in 2015 and have carried around in my memory ever since, “Tell me, what is it you plan to do with your one wild and precious life?

Wild Geese jolted me out of my anxiety and returned my attention to a larger perspective: that our wide world and the even more gigantic universe is flowing always, and I’m but a tiny speck in all those machinations. (Why is it so easy to lose track of that?) More important, Oliver’s words reminded me even though I’m a small speck I do have a place, and I only need to walk outside and look around to feel that flow of energy, and relax into it.

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.

That Feeling of Engagement

Talking last week with a friend who manages a team of software developers, and she was marveling at their level of productivity. To her it felt like 10x the throughput of a team she’d been a part of at a previous company, plus they were all having more fun.

Reminded me of a seminar where we identified the conditions that create a space for people to invest themselves and be deeply committed. It’s not just about clear vision and compelling mission (though those are important too). Engagement is highest when we feel we are highly valued; when we feel we’re part of a winning team; when our work is meaningful; and when there is an environment of trust.

So I asked my friend what is she doing to stimulate these factors? She herself wasn’t fully aware, but as we talked it became clear it could only be happening through the multitude of daily small conversations she has with her team and with each individual in the team. Sharing a sense of appreciation in each email or slack message. Holding her people accountable not through constant badgering but by being in the heat of battle with them. Being willing to climb into the foxhole and work side by side on the real problems. Yes, providing clear direction of where they were going and milestones to mark the way; yes, giving constant encouragement, having course-correcting chats when needed, and celebrating progress; and yet also taking time and care to listen to the people in her team, to hear their fears and support them when they feel frustrated.

Doesn’t matter at what level we are leading: Executives, directors, project managers, sports coaches, clergy, administrators, team captains, dorm leaders, teachers, parents, big brothers and sisters: anyone in positions of authority can influence how engaged we feel.

I am so impressed with my friend’s success, and I strive to emulate her. Leadership is a difficult and noble undertaking.

Quick Decisions

Ninety-five percent of business decisions can be undone, and a full reversal is almost never necessary. Usually, our informed intuition is directionally correct, and as we learn we can course-correct along the way.

This is a well known tenet in leadership literature yet it is powerful for leaders to digest and practice, especially if the team is driving toward big goals. The bigger, hairier, more audacious the goal, the more important it becomes to make decisions quickly.

An example: Early in my career, I used to wait until I was 80-90% sure of my decision before putting the team into motion. I was trained as an engineer and I craved the assurance of knowing I was making the right decision based on sufficient data. But the team needed sponsorship far before I could get that level of confidence. Left to their own, they made individual choices that caused confusion, created conflict, and resulted in slower performance. This actually became more of a headache to manage than if I’d made a 50% confident decision in the first place, then adjusted as we went.

Certainly, some decisions cannot be easily reversed. Selecting the right ERP system requires much more input and research than deciding how and when to introduce a process change, even a major one.

But most decisions can be tweaked and course-corrected if they are moving in the general right direction. Don’t fall into the trap of trying to quell your fears, cover your @$$, or flailing due to ambiguity, because you’re probably hurting the team more than you realize.

Daily Mantras

I will have a good time!

Attitude is EVERYTHING.

If it’s not what I want, I don’t say it.

It’s easy for me to change.

Words are previews of things to come.

I’m a doctor of human relations.

I am in the people business.

I am genuinely interested in other people.

I will ask a lot of questions today!

“Tell me more.”

I have an advantage.

I will watch the tone of my voice.

People are as interested in me as I am in them.

I’ll fake it ’til I make it.

I will speed up by slowing down.

It’ll come to me.

I will look for the good.

I will do more for everybody when I do more for me.

I will be a meaningful specific rather than a wandering general.

What I see is what I’ll get.

Repetition is the mother of skill.

I will act, not react.

I’m a money magnet.

Are We Accomplishing Anything?

People aren’t happy because they have stuff. They feel happy because they’ve accomplished things.

How do they know they are accomplishing things? How do they know they are accomplishing the *right* things?

It comes down to what we are measuring, and what we’re talking about every day, every week. Are we focused on the stuff that needs to get done, or are we talking about what we did last weekend? (No problem chatting about our personal lives, but that’s 1% of the conversation, not 5% or 50%)

Where is our scoreboard, and how often are we checking in on it? Are we celebrating each little victory that moves us closer to our goals?

If we don’t know how to measure what’s going on, then we don’t really understand the process of what’s happening.

Meaningful 1-1’s

I’ve seen loads of great ideas for managing effective 1-1’s with direct reports. Here’s one that I used many years ago, then drifted away from, and recently reinstated with excellent reviews from my staff.

It’s a 25-minute check-in with a “5×5” approach. It’s predicated on a quarterly establishing of goals for each team member. The format feels similar to that of a daily scrum.

5-10 min: What are 1-2 accomplishments since our last meeting that moved you toward your goals.

5-10 min: What 1-2 accomplishments are you aiming for before our next meeting.

5 min: Is there anything you need from me to get this done?

Twice a quarter (every 4-6 weeks) is a good cadence to ask, “What else is going on with you, where you do feel stagnant, in what areas would you like to keep growing, and what do you need from me to do so?”

I find that sticking to a playbook for 1-1 meetings accomplishes three things:

  • Maintain focus on quarterly goals;
  • Setting an expectation with reports about the purpose of this meeting;
  • Creating space for ongoing professional development conversations.

Communication Requires Context

We live in a world where we are affected by a social media stream where we are unable to effectively ascertain other people’s tone. This is very dangerous. If I’m walking on the sidewalk and you’re standing on the corner in my way, I can say, “Excuse me, can I get by” and from my tone you know there is no danger here, I’m not fighting with you, I’m not threatening you, and we can interact with each other peaceably. But on social media, where tone is absent, this same message is commonly misinterpreted as a rude shout: “EXCUUUUSE ME!! CAN I GET BY!!” perhaps heard with sarcasm or criticism. The receiver completely misunderstands the sender’s message and a dialogue turns toxic. We do this all the time; we misinterpret each other’s intentions because we don’t know each other.

Communication requires context.