Introducing Wayfinders Collective

Introducing Wayfinders Collective

I have always been a believer in putting out into the Universe the energy, ideas and intentions that I have for myself. After all, if you don’t lead with what you want, how will the Universe ever know what to send your way? 

As I’ve been finding my way through a recent career transition moment, I’ve noticed that others are also finding themselves in moments of change, of questioning: Where am I heading? What is my North Star? Is there even just one ‘right’ North Star for me, or perhaps am I in search of a constellation of stars, or a different galaxy altogether?

Then, one night as I sat eyes closed on a red-eye flight – literally on a journey across time and space – the Universe popped into my head with a message:

I am a Wayfinder.

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A Love Letter to Risk Taking

 A favorite window sign in Palo Alto, ground zero for risks, failure and resilience.

A favorite window sign in Palo Alto, ground zero for risks, failure and resilience.

As a child of Silicon Valley, I’m no stranger to the mantra of failure as a virtue. Fail fast to succeed sooner, they say. Failure is often talked about as a badge of honor, a show of strength and resilience, not something to hide or shy away from.

When you take a risk, you open yourself up to the possibility of failure. Thinking on my career over the last 15 years or so, I’ve actually taken a number of risks. I moved across the country to go to business school on a hunch that I needed to learn more and get exposure to new ideas. I accepted a job at IDEO without a lick of design training, all on instinct that the risk would lead me somewhere good in the end. I even agreed to move my entire family to Washington, DC to join a new startup in government, the Presidential Innovation Fellows program – a huge risk given that almost nothing about the Fellowship was fully tested and set in stone.

Recently I took one of the biggest professional risks of my career: signing on to open up the first US office for a talented organization of engineers, designers and technology strategists based in Europe. Talk about an untested experiment – this opportunity was all about trusting my instincts and jumping into the unknown. Yet again, taking a risk.

Thinking about it more, this big risk – saying yes to the job – was actually made up of a series of smaller risks that I also agreed to take on. Like a collection of puzzle pieces coming together and forming the whole. For this opportunity I took a risk joining a team I didn’t know, but that I instantly respected and connected with. I took a risk creating a role for myself that included new challenges and unexplored responsibilities, but that I was certain would help me flex new muscles and grow as a person. I even took a risk on the content of the work, moving out of my comfort zone of ‘easy’ topics and diving head first into novel conversations and vocabulary.

Everything about this big risk was exciting, fresh, invigorating and challenging – and I loved every minute of it. 

Unfortunately, yesterday I found out that this big risk I took – the one where I jumped into the unknown and embraced the experiment of trying – didn’t work out. Does that mean I failed? 

As our old pal Tennyson said, ‘Tis better to have loved and lost than never to have loved at all.” For relationships of all kinds, even professional ones, the truth is we have to take risks. We have to trust that we’re making a good choice based on the information we have, and then we have to be prepared to take a leap of faith on the rest of it. Really, everything is a risk. In the good moments of this latest risk, I laughed, I had fun, I enjoyed my teammates and our shared experiences together. In the bad moments of this risk, I struggled, I gritted my teeth, I toughed it out, and yes, sometimes I even cried. And in the end, taking this risk forced me to stretch myself, learn new things and become a stronger leader. 

Taking risks requires bravery. It requires being vulnerable, opening yourself up to something untested and unknown, and spreading your arms out wide to see what comes back to you. In this way taking a risk – whether in a new professional capacity, in a new personal relationship, or in some other way – is actually the opposite of failure. You fail when you say no instead of yes. You fail when you don’t try. You fail when you don’t learn. 

In the end, I took a risk. I tried something new. And it didn’t work out. But no – I definitely didn’t fail. 

So to all my fellow risk-takers out there, I say, ‘Onward!’ Oh, and to anyone who’s hiring, I’m ready to say yes to my next risk.

First Day / Last Day

Yesterday marked my last day as a White House Presidential Innovation Fellow

When I joined the PIF program in September 2014, I didn’t do it out of a love for my country. Sure, the public service element was meaningful to me from the start, but I never would have used the word ‘patriotism’ to describe my reasons for joining. My reasons were more personal, perhaps more selfish – career growth, new opportunities for my family, that sort of thing.

As soon as I got started, it was clear I was in a fight to swim upstream. It turns out that getting stuff done in government can be even tougher than it looks from the outside, especially on a short timeline. The reality is that there have been many moments over the last two years where I have raised my hands in frustration and wished I could quit. 

Yet, as I wind down my stint as a Fellow, I can’t help but feel immense pride at having witnessed and perhaps even played a part (albeit a very, very tiny one) in the impact and legacy of the Obama Administration. It may just be coincidence that I am concluding my federal service as our next election is picking up speed, but watching the battle taking place – for our new leader and for the future of this country – I now understand what’s truly at stake, as well as what’s truly possible when people come together in service of mission that’s bigger than themselves.

Over the last 23 months, it has been a personal honor and privilege to serve my country in the way I know how, to do my part to make our government more efficient, effective and ultimately more successful in meeting the needs of the public. It’s been an experience full of big lessons and small victories, and I am so grateful for all of it. Thank you to all of my friends and colleagues at the Presidential Innovation Fellows Program, the White House, and across the government for inviting me in with open arms and supporting me over the last two years. 

While it’s bittersweet to close this chapter, I’m moving on with an expanded understanding of my own identity and purpose as an American citizen and patriot. I didn’t start out on this course because of my love for our country, but I am certainly leaving with it. 

Toddler Parenting: The Ultimate Crash Course in Being Effective at Work

 Me and my little 'extreme user'

Me and my little 'extreme user'

Demanding. Frustrated. Stubborn. Selfish. Emotional. Impatient.

If you’ve ever had a tough boss or a tough client, you’ve probably privately used some of these words to describe him or her. 

Yet, if you’re a parent, you know that these adjectives can also easily be applied to another tough crowd: our children.

As my son makes the transition from infant to toddler to preschooler, I’ve been reflecting on how parenting has changed me as a person and as a professional. My theory? Parenting is by far the best crash course – the best on-the-job training you could hope for, really – for improving your effectiveness and success at work. Here are my top three parenting lessons that also help me at work:

Communication and Empathy are #1

The craziest thing about little kids, even ones who are too young to talk, is that they are constantly communicating with you and you are constantly communicating with them. Whether it’s through your words, your body language, your eyes, even your energy – our children soak up all of these cues even when we don’t realize it.

Parenting requires you to be constantly vigilant about what you are communicating and how you are communicating it. Every signal sends a message. For instance, using words to describe our planned activities for the day helps my son create a mental script that he can follow and find comfort in as we move throughout the day. Similarly, If I’m nervous about my son’s doctors appointment, even if I don’t communicate that message verbally, my body language might tell my son that we’re about to enter a situation that makes me anxious, which in turn creates anxiety for him.

In crisis moments, communication – and especially communicating empathy – becomes especially important. One of my favorite parenting books, Love and Logic, outlines a step-by-step process for how to tame a toddler meltdown. The first step is called “locking in the empathy”. Simply put, this means getting down on on your child’s level, making eye contact with them, and starting first by expressing your understanding for their feelings and emotions. By showing your child that you are focusing on him and his experience of the situation, you’re much more likely to make progress trying to calm him down and move on to the next thing.

As professionals, this emphasis on communication and empathy is equally important. Whether it’s making a recommendation for a new strategy, having a tough conversation, or simply nurturing a professional relationship, being mindful about how and what we communicate is vital both for our clients and for our colleagues. How often and how well do you communicate the planned activities for any given client project, or lock in the empathy with a tough colleague who’s not making things easy for you?

Life is about Choices

This is perhaps my favorite toddler trick and it’s all about control – or at least the perception of control. Being a toddler is tough for a lot of reasons, but a big one is that you’re self-aware enough to want to have free choice and independence, but at the end of the day you’re still two years-old, which means you get to do practically nothing on your own (at least, this is what I think being a toddler is all about). When a toddler confronts this inner conflict head on, it’s like instant internal combustion. So, to help ease this disconnect, you offer choices. 

Love and Logic talks about offering choices that are first, equally acceptable to you and second, don’t knowingly cause any harm to anyone. To demonstrate this, imagine a scenario in which you struggle every night to get your child to eat vegetables at dinner (in my experience, this is a very likely scenario). You don’t care what vegetables your child eats, but what you do care about is that he has something green on his plate. Instead of asking him, ‘would you like vegetables or a cookie at dinner,’ you ask him, ‘would you like broccoli or green beans with your dinner?’ All of a sudden, the conversation has shifted to one about choices, and usually this is enough. Your toddler feels in control of the situation, and your end goal of getting something green on the dinner plate is accomplished (although whether he eats it is another story). 

Since learning about the mind-blowingly effective world of toddler choices, I’ve started playing around with choices at work too. It’s been especially helpful with colleagues when I need to engage them in a conversation about pivoting or redirecting our work to focus on something unexpected. With a little bit of pre-planning before the conversation, I can pick a couple of choices – either of which will work for me – and then present them to the group for discussion. By selecting a few options that I’m ok with and then letting go of the final decision, I’m able to steer the group in a direction that I feel good about, while still including others in the process and giving them ownership of the final decision. 

Staying Present and Mindful

By far one of the toughest things about parenting is that our children make it tough to multi-task. Those pesky kids with their needs and wants! 

In truth, while we all love to check email while watching TV or doing any number of things at the same time, being a parent forces you to put down your devices, your to-do list, and pretty much everything else and focus completely on your child. Parenting is, in fact, the best form of mindfulness training you can find. Some of my happiest, most fulfilling, and most memorable moments with my son are the ones when I am able to drop completely into parent mode: sitting on the floor building a train set, listening to my son describe his day at school, getting lost in the plot of a playful library book. I may never finish cleaning the house or doing laundry, but I’ll also never regret the moments when I stopped worrying about chores and errands and instead spent my time being completely present with my son. 

Being present at work often feels in direct conflict with what I’m supposed to be doing at work, which is being productive. How can I let go of my to-do list and be present at the office when my inbox is overcrowded and my calendar is filled with meetings? My approach to this is to find moments of being mindful in the midst of the day’s chaos. This could look like any number of things, but right now for me it looks like closing my laptop when I’m in a meeting so I can focus on the conversation. It looks like asking how my teammate’s holiday was, and then genuinely listening to the answer. It looks like enjoying the progress my client makes in a workshop, without worrying about the work that inevitably comes next. 

At IDEO, I learned about the value of looking to extreme users, or edge cases, for insights into how to design solutions or services that work for everyone. Three years into my parenting journey, I can safely say that toddlers are most certainly extreme users! 

How has being a parent changed your approach at work? I’m curious to hear what you think.

Three Lessons from Three Years at OpenIDEO

This February marked my three year anniversary as a member of the OpenIDEO team at IDEO – amazing how the time has flown!
Maybe it's because I'm marking this anniversary, or because our team is growing and I find myself training and coaching new colleagues, but I've started reflecting on how OpenIDEO has evolved over the last few years – and by extension, how I've evolved with it. When I joined OpenIDEO way back when, our platform and our community was less than six months old. We were an exciting new initiative in IDEO's eyes, and yet most of our colleagues weren't quite sure what to make of us. We were small, scrappy and said yes to (almost) everything for the sake of continued learning and growth. We knew enough to be dangerous and had some hunches about where we were headed. But beyond that, the rest was open, white space.
Joining OpenIDEO marked a true departure and a leap of faith for me: prior to IDEO I'd never worked in technology, I'd never been part of a startup, and I'd certainly never imagined I'd join a design company. Even with all of these unknowns, it was a no brainer to jump in with both feet.
One of the cool things about joining OpenIDEO when I did is that I've had the chance to be around long enough to see our efforts grow and blossom. Ironically, in a world of fast-moving, short attention-span startups (and the employees behind them), having some staying-power has enabled me to get mired in the details AND see the forest for the trees, so to speak. As I round out Year 3 and move into Year 4, here are a few highlights of what I've learned and how I've grown so far:
Finding Comfort in Chaos
When I first joined OpenIDEO, I was looking for structure. Ten months into what felt like a topsy-turvy, post-MBA job search that I had no control over, I viewed my IDEO offer letter as the guarantee of stability I was craving. How wrong I was! Instead, what I found was a brand new business with a largely unwritten future. Admittedly, in my first year at IDEO this mismatch was really challenging for me. I often found myself feeling inwardly resistant to conversations or projects that seemed too chaotic, or simply wishing we could have figured out all this messiness already. Everyone talked about things like 'experiments' and 'iteration' – and in truth, at the beginning of my OpenIDEO tenure, I often wanted to run screaming in the other direction.
Being a natural project manager, though, my inner organizer eventually took over and I started creating the structure I needed. In the beginning, this meant nailing things down, making quick decisions and clamping down on anything that felt ambiguous or undecided. Not surprisingly, I wasn't so successful in those early days – not only was that way of working not in line with our cultural and team values, but it wasn't any fun either. Later, I learned to move forward in my work by creating a skeleton outline – just enough structure to give myself a North Star to follow, while also still leaving a bit of room for spontaneity and unexpectedness.
At the time I thought I was just trying to wrap my arms around something to force it to make sense. Now, however, I can now look back and say that the experience of creating something out of nothing, of finding comfort in the chaos, was hugely valuable because it pushed me to do the very thing I was resisting – namely being flexible, not having all the answers from the outset, and learning to be comfortable with iterating along the way.
The beauty of working in a startup – as chaotic as it can be – is that in the chaos, there is possibility. There is growth and movement and fluidity in ways that you don't experience when you're working in a more traditional, 'pre-built' organization. Yes at times it can feel frenetic or unstructured…but strangely enough, this way of working has rubbed off on me. In fact, I can now say that I proudly use words like 'prototype' and 'test' in a sentence! Only this time around, it's not just jargon – I believe it.
Speak Now…or Don't
Prior to joining OpenIDEO, I'd worked in pretty traditional, hierarchical organizations where rank mattered. Where I sat in the food chain not only influenced the work I could do, but it affected the opportunities I had to participate in conversations. Because of this, I got trained (for better or for worse) to often times keep my opinions to myself. When I did speak, I agonized in my head: when was I going to chime in? what would I say? what questions will other people ask and how will I answer? It was exhausting.
One major shift that caught me off guard at IDEO was that suddenly, people wanted to know what I thought about things. Unlike other organizations, OpenIDEO (and IDEO more broadly) has a fairly flat structure and culturally, we value healthy, constructive dialogue and inquiry. This meant that, at any number of times during a day, my teammates, my manager, other folks at IDEO would ask, 'Ashley, what do you think?'. Other times, they wouldn't even bother asking – the expectation was that I would just dive right in.
While this may sound like a breath of fresh air, it was actually very challenging for me. Outside of some impassioned conversations in MBA team rooms, I actually didn't have much practice using my voice. So, when pushed for a point of view on something, I instead turned inward and became speechless. While I'd always thought of myself as an extrovert, every day I sat in a roomful of extroverts who were well-practiced in speaking up – and suddenly the introvert in me switched on.
That's not to say that I didn't have an opinion; in fact I had opinions about everything! I just didn't know how to share them.
Over time, and with the support and coaching of my manager and others, I slowly started practicing speaking up. And believe me, it takes practice. But incredibly, through this practice I don't just feel more comfortable going through the motions of speaking my mind. Instead, I've come to trust even more in the content I have to share. Maybe it's that I've been doing this long enough to have that are rooted in real work and a real understanding of what we do, maybe it's just something I've been practicing long enough that it feels less rehearsed and more spontaneous. Whatever the reason, it's a liberating feeling to have a point of view and feel confident enough to share it.
There's No Substitute for the Real Deal
At OpenIDEO, we're quick to celebrate the online partnerships and virtual teams that form on our platform. After all, we're an online tool – which means 99.9% of what our community does is online too.
For our team at IDEO, the same is true: our 10-person group is actually made up of a collection of people across multiple locations: the U.S., the U.K., New Zealand, even Eastern Europe. Amazingly, there isn't actually one time during the day when we can all get on a phone call together. At first this was incredibly frustrating and felt agonizingly slow (even now, when the phone or video connection is poor, it's easy to want to pull your hair out). But as they say, necessity is the mother of invention – and working as part of a virtual team means getting creative. Whether it's finding new tools to support our online brainstorming sessions or establishing new rituals that support our team to form bonds across time zones, we're definitely seeing some advantages to working this way.
My sense is the trend these days is to further shift the balance toward virtual teams – and I'll admit that it's a skill I've worked hard to acquire. Nonetheless, one final learning from the last three years is that there really is no substitute for the 'real deal'; that is, in-person, face-to-face connections and collaborations. On the OpenIDEO community side, we're starting to see incredible traction when community members take their efforts 'offline' and continue their collaborations locally as a team. You can check out some great examples here. And for our team, we're all starting to coalesce around the idea that certain projects 'live' in certain locations. It helps us focus, it means that projects can move forward more quickly, and it gives each local team the chance to form an identity and a bond.
It's funny to look back on the last three years and wonder whether these lessons have been ones unique to working at a place like IDEO, or whether I'd have caught up to them at some point somewhere else. I'm not much of a risk taker, but I can say now that I jumped into IDEO with both feet – even though I had no idea what I was getting into.
One more note: even though these are lessons I've learned, I'll admit I still have to practice them everyday. At times I still struggle in chaos, lose my voice or miss feeling an in-person connection. Some days are easier than others. Three years in, though, I'm thankful for the journey and learning so far – and I'm excited to see what the lessons are in Year 4!

A desk with a view

This February marked my three year anniversary as a member of the OpenIDEO team at IDEO – amazing how the time has flown!

Maybe it's because I'm marking this anniversary, or because our team is growing and I find myself training and coaching new colleagues, but I've started reflecting on how OpenIDEO has evolved over the last few years – and by extension, how I've evolved with it. When I joined OpenIDEO way back when, our platform and our community was less than six months old. We were an exciting new initiative in IDEO's eyes, and yet most of our colleagues weren't quite sure what to make of us. We were small, scrappy and said yes to (almost) everything for the sake of continued learning and growth. We knew enough to be dangerous and had some hunches about where we were headed. But beyond that, the rest was open, white space.

Joining OpenIDEO marked a true departure and a leap of faith for me: prior to IDEO I'd never worked in technology, I'd never been part of a startup, and I'd certainly never imagined I'd join a design company. Even with all of these unknowns, it was a no brainer to jump in with both feet.

One of the cool things about joining OpenIDEO when I did is that I've had the chance to be around long enough to see our efforts grow and blossom. Ironically, in a world of fast-moving, short attention-span startups (and the employees behind them), having some staying-power has enabled me to get mired in the details AND see the forest for the trees, so to speak. As I round out Year 3 and move into Year 4, here are a few highlights of what I've learned and how I've grown so far:

Finding Comfort in Chaos

When I first joined OpenIDEO, I was looking for structure. Ten months into what felt like a topsy-turvy, post-MBA job search that I had no control over, I viewed my IDEO offer letter as the guarantee of stability I was craving. How wrong I was! Instead, what I found was a brand new business with a largely unwritten future. Admittedly, in my first year at IDEO this mismatch was really challenging for me. I often found myself feeling inwardly resistant to conversations or projects that seemed too chaotic, or simply wishing we could have figured out all this messiness already. Everyone talked about things like 'experiments' and 'iteration' – and in truth, at the beginning of my OpenIDEO tenure, I often wanted to run screaming in the other direction.

Being a natural project manager, though, my inner organizer eventually took over and I started creating the structure I needed. In the beginning, this meant nailing things down, making quick decisions and clamping down on anything that felt ambiguous or undecided. Not surprisingly, I wasn't so successful in those early days – not only was that way of working not in line with our cultural and team values, but it wasn't any fun either. Later, I learned to move forward in my work by creating a skeleton outline – just enough structure to give myself a North Star to follow, while also still leaving a bit of room for spontaneity and unexpectedness.

At the time I thought I was just trying to wrap my arms around something to force it to make sense. Now, however, I can now look back and say that the experience of creating something out of nothing, of finding comfort in the chaos, was hugely valuable because it pushed me to do the very thing I was resisting – namely being flexible, not having all the answers from the outset, and learning to be comfortable with iterating along the way.

The beauty of working in a startup – as chaotic as it can be – is that in the chaos, there is possibility. There is growth and movement and fluidity in ways that you don't experience when you're working in a more traditional, 'pre-built' organization. Yes at times it can feel frenetic or unstructured…but strangely enough, this way of working has rubbed off on me. In fact, I can now say that I proudly use words like 'prototype' and 'test' in a sentence! Only this time around, it's not just jargon – I believe it.

Speak Now…or Don't

Prior to joining OpenIDEO, I'd worked in pretty traditional, hierarchical organizations where rank mattered. Where I sat in the food chain not only influenced the work I could do, but it affected the opportunities I had to participate in conversations. Because of this, I got trained (for better or for worse) to often times keep my opinions to myself. When I did speak, I agonized in my head: when was I going to chime in? what would I say? what questions will other people ask and how will I answer? It was exhausting.

One major shift that caught me off guard at IDEO was that suddenly, people wanted to know what I thought about things. Unlike other organizations, OpenIDEO (and IDEO more broadly) has a fairly flat structure and culturally, we value healthy, constructive dialogue and inquiry. This meant that, at any number of times during a day, my teammates, my manager, other folks at IDEO would ask, 'Ashley, what do you think?'. Other times, they wouldn't even bother asking – the expectation was that I would just dive right in.

While this may sound like a breath of fresh air, it was actually very challenging for me. Outside of some impassioned conversations in MBA team rooms, I actually didn't have much practice using my voice. So, when pushed for a point of view on something, I instead turned inward and became speechless. While I'd always thought of myself as an extrovert, every day I sat in a roomful of extroverts who were well-practiced in speaking up – and suddenly the introvert in me switched on.

That's not to say that I didn't have an opinion; in fact I had opinions about everything! I just didn't know how to share them.

Over time, and with the support and coaching of my manager and others, I slowly started practicing speaking up. And believe me, it takes practice. But incredibly, through this practice I don't just feel more comfortable going through the motions of speaking my mind. Instead, I've come to trust even more in the content I have to share. Maybe it's that I've been doing this long enough to have opinions that are rooted in real work and a real understanding of what we do, maybe it's just something I've been practicing long enough that it feels less rehearsed and more spontaneous. Whatever the reason, it's a liberating feeling to have a point of view and feel confident enough to share it.

There's No Substitute for the Real Deal

At OpenIDEO, we're quick to celebrate the online partnerships and virtual teams that form on our platform. After all, we're an online tool – which means 99.9% of what our community does is online too.

For our team at IDEO, the same is true: our 10-person group is actually made up of a collection of people across multiple locations: the U.S., the U.K., New Zealand, even Eastern Europe. Amazingly, there isn't actually one time during the day when we can all get on a phone call together. At first this was incredibly frustrating and felt agonizingly slow (even now, when the phone or video connection is poor, it's easy to want to pull your hair out). But as they say, necessity is the mother of invention – and working as part of a virtual team means getting creative. Whether it's finding new tools to support our online brainstorming sessions or establishing new rituals that support our team to form bonds across time zones, we're definitely seeing some advantages to working this way.

My sense is the trend these days is to further shift the balance toward virtual teams – and I'll admit that it's a skill I've worked hard to acquire. Nonetheless, one final learning from the last three years is that there really is no substitute for the 'real deal'; that is, in-person, face-to-face connections and collaborations. On the OpenIDEO community side, we're starting to see incredible traction when community members take their efforts 'offline' and continue their collaborations locally as a team. You can check out some great examples here. And for our team, we're all starting to coalesce around the idea that certain projects 'live' in certain locations. It helps us focus, it means that projects can move forward more quickly, and it gives each local team the chance to form an identity and a bond.

It's funny to look back on the last three years and wonder whether these lessons have been ones unique to working at a place like IDEO, or whether I'd have caught up to them at some point somewhere else. However they came to me, and even though I call these my lessons learned, I'll admit I still have to practice them everyday. At times I still struggle in chaos, lose my voice or miss feeling an in-person connection. Some days are easier than others. Three years in, though, I'm thankful for the journey and learning so far – and I'm excited to see what the lessons are in Year 4!