She’s a scrum master

She’s a scrum master

I am writing this post to explore a few things about this scrum mastering potential lover as well as the interactions I have had with a handful of people over these last few weeks. Interestingly, I managed to collide with these people simultaneously.

Unfortunately, I am running into friction with each person. As a UX designer, I understand friction can mean good things, but if it’s not handled properly then it typically leads to unfavorable outcomes for all involved.

The friction seems to stem from the way I am presently creating first impressions, the way I frame who I am and what I do, and my inconsistent responses to a series of the same questions that each person seems to be asking in a similar fashion. Not that blame is ever an acceptable option, but realizing that I am the common denominator in each of these friction-filled situations was my first obstacle.

I certainly don’t believe in magic, but I do believe that there’s something valuable to learn here. I’m not sure what exact lesson I am looking for just yet, but I can sense that it will emerge as this post unfolds. Perhaps the exercise of writing through this ambiguous moment of my life will result in somewhat of a self-assessment.

Let’s see where this goes.

As I mentioned, and will continue to brag about, I met a woman. She’s a scrum master. She’s smart. She’s bold. She’s beautiful. She’s classy.

I know it’s a new and exciting thing so I’m trying to not to get too emotionally invested early on. I will let you know if it turns out to just be the nuanced novelty that comes with nearing the edges of intimacy. Until then, I will attempt to discern any valuable insights that she may have as her feedback is highly encouraged.

In addition to the sassy scrum mastering madam, I met a few entrepreneurs that I feel comfortable working alongside as peers, I established a feedback loop with a local impact investment fund, and I started scoping out a partnership with a mentor-driven impact investor. I’m not sure if “mentor-driven impact investor” is a thing or a phrase, but I am coining it right now.

To sweeten the pot, each person I met over the last few weeks seems to be a circle of influence who was then introducing me to another circle of influence. It is the ideal scenario for my work to be in an environment where it will scale. The fact that I’m having an initial phase of friction is perhaps a good thing because it means I wasn’t ready for what’s about to happen just yet. The pieces seem to be aligning which is one of the more exciting things that I look forward to enjoying in the near future.

To be specific about why I think I’m experiencing friction with the scrum mastah and future colleagues, without realizing it, at some point in the last few months I started introducing myself to all of these people in the most unattractive, under-stated, unprepared, unsexy, yet honestly transparent manner that I ever have. I basically said I was a designer, but even that took ten minutes to get out of my mouth.

Regardless of who I spoke to, I had a different “pitch”, if you even want to call it that, for everyone. I understand I’m supposed to have a different pitch for different settings and people. However, my different pitches were whatever came to mind at the time I interacted with someone. I would just react to each person’s questions on the spot. “Hi, Daniel. What are you working on right now?’ I probably said a different answer to that question to nearly 10 people.


Inconsistency is in itself a problem, but what that inconsistency says about my state of my mind is perhaps the underlying problem. Inconsistency seems to be the symptom I am experiencing.

There a few symptoms like the inconsistency I just mentioned, and there’s a systemic issue or issues that may require me to fundamentally change the way I view myself, the way I prepare for battle, the way I react to situations, and the way I shape my emerging future. These are essential elements of intentionally constructing the culture of any organization.

This brings me back to the recurring questions that the sexy scrum master and other individuals I am interacting with seem to have trouble discovering about me:

What I have done?

What am I doing?

Where am I trying to go?

Anytime I engage in a new project of any kind, each person involved is either trying to get the others to listen to their answers to the above or they are doing what they can to avoid answering. I have been exercising the latter without realizing it. Not only is it creating friction between myself and other humans, but the impact that friction could have on the outcome of the present day is what I have overlooked.

Peers over Mentors?

As I continue to grow it gets more difficult to find mentors. This has been another conflicting element that presents itself as an obstacle. The two previous mentors that I attribute much of my early success to both play a much different role today than they once did – they don’t play any role. The relationships evolved into things that ended up holding me back instead of propelling me forward. After speaking with some friends and researching the topic online I discovered that this is a common issue for many. There is a tasteful way of transitioning out of these relationships which I am now equipped with for the future.

There is a lot of info out there about outgrowing mentors.

Warren Buffett calls them his ‘heroes’ — not necessarily mentors, but different people who bring different aspects to his life as he changes and grows,” she said. “You don’t need just one because you may need different mentors for different departments.”

This article talks about why a peer-network of entrepreneurs who are struggling with the same type of challenges as I am is superior than the traditional “mentor” that we typically of think of when we think of mentors.

To know that I wasn’t alone is helping me quickly move around this obstacle. This was initially a big issue for me and I convinced myself that I wasn’t good enough to continue my pursuit. Now I see it’s just another obstacle that has a series of strategies to overcome it.

The lesson I am taking from this is to focus on finding entrepreneurs solving similar problems as I am so we can mentor each other, share our resources, cross-sell customers to our peer’s products and services, and add our value to our peer’s value proposition so that each organization generates more revenue as we grow our businesses together.

Confronting Obstacles Immediately

Identifying obstacles and planning out their removal is something I need to be more intentional and aware of while working on any project solo. Most of the things in this post are things I help entrepreneurs with as they develop their own projects in our incubator. I have a difficult time remembering to also apply the same principles to my own life. Without doing so, I am unable to focus on the work I love the most.

Guiding Principles for Prioritization

“How do I determine what the priority is for today?”

I will be setting up guiding principles to work within to help me focus on the most important items in my backlog one at a time.

I am learning that sometimes the difference between success and failure is so incredibly small that I lose sight of it because it’s in sitting right in front of me. Hidden in plain view. This disorganization I speak of – my inability to focus on the right thing – is the result of my last decade where I woke up each morning and took a leap into the world. “This is who I am. This is what I believe. Love me for who I am or leave me for who I am not.”

Honestly asking myself “why”

Is this obstacle something that is preventing me from reaching the next level of success? Is this obstacle something that is preventing me from accessing unique growth opportunities in my personal and professional development? Why is this happening? Why did I arrive at such disorganization?  Why, why, why? Focus on reaching the underlying systemic issue so that I am not distracted by the symptoms.

Nailing my pitch

Nailing my pitch is a requirement. Not only because it produces better results in my interactions in everyday life, but also because having the ability to nail the pitch at any given moment means that I am organized, focused, and confident in my ability to realize this vision.

The scrum master naturally sized me up from day one. She wanted to know who I was, what I have done, what I am doing, and where I am going. As did each other stakeholder of the DC impact community I interacted with. It’s really just these three questions:

What have I done?

What I am doing?

Where I am going?

I take a lesson from this by understanding how critical first impressions are and how there is so much extra baggage attached to that impression which is obviously reflected by the nature of the impression. If I was focused and organized I would have likely made a strong and positive impression.

Watching myself participate in conversation after conversation with incredible people, and, in each case, watching myself create a perception of myself that I knew was inaccurate – in real-time I knew I wasn’t painting the right picture. I knew I wasn’t on point. I watched person after person react to this perception I created and I thought to myself, “This person has no idea who I am, what I’ve done, what I’m doing, and where I’m trying to go.” At the same time, was I even prepared to tell them?

What have I done?

What am I doing?

Where am I trying to go?

The Journey Line

The scrum master diagnosed and prescribed the Journey Line exercise to me a few weeks ago. It sounded cool – I wanted to explore it, but I didn’t put it as a top priority. Why didn’t I place it as my next move? Because what the heck did she know? There is so much about my life she didn’t know – so much that I bring to the table that she is unaware of -so many other things on my plate right now – how would she know what I should be prioritizing right now? For me to pick up a new “to-do”, learn about it, research it enough to feel confident in the process would only get in my way.

What if, though, I needed something to get in my way? Writing through the details of what’s been happening in the paragraphs above makes it quite obvious that I wasn’t doing myself any good to continue with the self-deprecating cycle of being comfortable not being myself.

Perhaps she was right in suggesting this Journey Line thing. It says something about the integrity of this woman for the way she brought it up to me. She brought it up as something that sounded really awesome to me. I appreciate that she brought it up this way rather than her being critical of me and telling me that I needed to get my sh*t organized. Ya know what? I bet her presentation of the Journey Line exercise and the delivery of her message is why I am even writing this blog post about the impact it’s had on me.

Perhaps overcoming an obstacle, the right obstacle, is just what I need.

Perhaps it was time to find out just what this obstacle was – who knows, maybe this scrum master is, in fact, a master.

Last night, I decided to do my due diligence on the scrum master’s prescription.

Journey Lines is an activity that fosters self-organization and cross-functional behavior because it reveals a person’s skills, experiences, background, etc. This way, the rest of the team knows what this person “brings to the party.”



I know.

That, up there, is the definition of what she casually brought up to me a few weeks ago after she experienced the issues I mention above.

My next post will be titled The Journey Line, and it will include a short video where I walk through the milestones that make up my journey line. Would be great to get your feedback on that – it will be up today – News Year’s Eve 2016.


I have talked a lot about how I have misrepresented myself and how that’s bad for me, but it’s also bad for the other person to interact with someone when it feels like you’re speaking different languages and not really understanding where the other is coming from.

If I can’t convey my message effectively, then I am not creating the conditions for our interaction to collectively spark into something bigger which is more important to me than making something alone.

If the friction isn’t discussed, ironed out, and continues to grow between us than I might as well drive a wedge between us now and stop trying because we’ve already failed before having an opportunity to see what’s possible.

There was a time when I knew I had to always have my house in order before marketing myself and always made sure my conversational value prop pitch was rock solid sexy. Perhaps a simpler way to put most of what I have already stated is that I became comfortable living in this disorganized state, or should I say chaos, simply because I had the skills to survive regardless of the conditions. Catching this now is something I am grateful for because it seems like something that would get overlooked or ignored by me until 10 years went by and I woke up in the same place I am right now.




My Mount Everest

It’s been difficult to find an ecosystem where my specific organization would sync up just right. The closer I get to reaching the top of this mountain seems like it’s only gotten more challenging to continue climbing. I am looking forward to looking back on my Mt Everest and talking about what it was like to start walking towards the horizon when I couldn’t even see the tip of the mountain because it was surrounded by the clouds.

Write the next chapter

Looking back on the discovery of such incredible human capital these last few weeks, thinking about what I have been working towards since 2009, and as I write these words for you I am beginning to envision what the next chapter will look like for myself.

Unlike the previous chapters of my life which were typically being written as I lived, I am going to approach this next chapter a bit differently. I am going to write out this chapter so that I am able to benefit from the lessons I am learning and not make the same mistakes again. Since I was a kid, I got myself in trouble for being too impulsive. I can’t tell you how many times my mother said, “Dan, you have to stop, and think.”

This was therapeutic

I feel satisfied at the moment. I feel focused. I am not at the level of clarity and focus I am looking for just yet, but I am going to reach that state once I complete a few top priorities from my backlog.

How does all this circle back to that scrum mastering model that I mentioned earlier? Well, who knows if she’ll make her way into a place in my life and I in hers. The excited feeling of nearing the edges of intimacy with someone who knew how to challenge me in such a way to help me grow is something I will bring forward with me.

As we talk through these ideas together I can’t help but take notice in what now seems obvious. Getting the most value from a framework like scrum might only be realized after a person decides to live and be scrum through their own lives. It’s not exactly something you turn off and on.

Scrum is a framework within which people can address complex adaptive problems, while productively and creatively delivering products of the highest possible value.

Perhaps more exciting to me is how closely inline the scrum framework is with the framework we implement at PreThinc.

Next steps

  1. Journey Line exercise

  2. Sketch out 2017

  3. PreThinc’s product backlog

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