Danielle Strachman

Danielle Strachman’s passion for disrupting education led to her current role, as Director of the Thiel Fellowship.  After graduating college in 2002, she decided to go the entrepreneurial route instead of enrolling in a PhD program. Leaving behind everything she knew, she moved to California where she started an educational consulting business serving the homeschooling community. It was this group of passionate and driven young people who inspired her to create Innovations Academy, a charter school in San Diego, which she led for 4 years.  Now, leading the Thiel Fellowship is a perfect fit with her drive to transform education, her love of entrepreneurship, and her fascination with science and technology.

I interviewed Danielle because her role in the 20 Under 20 program means that she thinks a lot of time thinking about how to support and nurture self-direction.  She’s also a wonderful example of a person who brings meta-learning and core skills to incredible young people and as she said in the interview below, “even self-directed people benefit from modeling and clear expectations, and it’s even better if the modeling and the expectations are as explicit as possible”.



Lisa:  I’m interviewing amazing self-directed learners and people like you, who are themselves life-long learners but who also spend time supporting and mentoring excellence in others.   I have a collection of skills I call the MetaLearning toolbox but I’d love to hear what skills you, as director of the fellowship, regard as critical for helping your community take full advantage of the amazing opportunity they have through the Fellowship.

Danielle: A couple of things come to mind, but first is the skill of reflection…being able to take a step back and think about what you’ve been doing and if it’s working, or not. What new directions you might want to take?  Even if you do something alternative you can still get in a tracked frame of mind.  Or a set idea of yourself like “I am a chemist”.  And there may not be a lot of time to question what that means.  Do those values still fit with me?  Am I changing?  Or maybe you’ve noticed that your outside hobbies have really taken off…there might be use in wondering what’s up with that?  I believe that people don’t take enough downtime to really reflect on things.

One practical tip which I use myself is to put “reflection time” on my calendar.  A lot of the time it gets eaten up by other things going on but it’s always on my calendar to remind me “this is important; make time for this” even if, out of the 3 hour block, I only take a half hour to take a step back from what I’m doing to think about things like “how’s the fellowship going?” for instance.  So I have a chance to see how different things tie together and wonder is this, or that, the right thing to be doing…

It can be really easy to get sucked into the momentum of something and then realize later that it isn’t the right thing.  Only when there’s a catastrophic moment does it occur that it might be the wrong focus or maybe there’s something else that would make better use of my talents and skills…something else I gravitate towards but I’ve been ignoring it.

We do a lot of reflection in the fellowship.  The Fellows send us a reflection form every month and then we have reviews every 3 or 4 months where we do a higher level reflection on how things are going.  We’re trying to build in assessment tools around reflection which is difficult because assessment is hard but we want to keep heading more in that direction.

Lisa: Generally, how hard is reflection for the Fellows?

Danielle: I don’t know if what I’m experiencing is just a reflection of the Fellow and Summiter communities or if this generation is particularly insightful but what I see in the people that I work with is that they are super open to it.  Even in the application stage, we ask a lot of reflection questions.  “Tell us about a larger project or undertaking and what were the learnings from that?”  They’re pretty open to it and they’re pretty good at it.  I don’t know how often they do it on their own.  But overall I see that this group of young people is interested in self-reflection and personal development in general.  When we started the Summit community the first year we had 150 (this year it will be 350) and there were certain sessions I wasn’t sure that young people were going to be interest in, like communications skills and NVC.  Someone gave a great talk at one of our Summits about deep listening and empathizing with others and I was really taken aback that even the young men, were feeling that it was really important stuff and saying “I’ve got to get better at this”.  I was very pleasantly surprised.  And it was a packed session.  It was [ topic here from Danielle ], about really listening to another person; she had people pair up and share with each other, which is often hard for everybody, not just young people.  The fact that they were whole hog into it…I was really impressed.  I’ve been really impressed with the young people I get to interact with.  Their level of self-reflective skill and willingness is really high.

Even when we’re gone out to high schools and colleges, and we’ve asked them more reflective questions, though sometime it takes them time to think about these things like “how’s that going for you” or “what do you think you’re next steps might be?” they want to engage in those types of questions.

I was talking with a young woman from Columbia who was having a hard time.  She was pre-med and she didn’t like the classes and she felt so much pressure to maintain her grade point average and it just wasn’t working out for her. She decided to drop the premed designation and was looking at some other things to do and I started asking her some questions like “when you were a little kid what were you really passionate about?” to try and help her explore directions she might go.  She was really engaged in the conversation and I got the impression that no one was asking her these types of questions.  So I really wish that guidance counsellors (and I get that there are competing time interests), teachers, parents, even student-to-student took the time to ask the questions which help people to look at how things are really going. Like, let’s talk about it now, earlier rather than later before you’re so far down the rabbit hole that you don’t know how to get out.

So this young woman was really engaged in the conversation and I could tell that she really wanted more of it.  So there needs to be Socratic Dialogue…so important and it was missing from other conversations in her life.

Lisa: Socratic Dialogue is really interesting!  It is so important for mentors to support Fellows in this way but also, you’ve raised the possibility that the same kind of support can come from colleagues and friends etc.  Some of making this happen depends on Creating a Culture.

D: Definitely.  It IS about creating a culture.  And that’s difficult.  The fellowship is going into it’s fourth application cycle and at our last retreat we probably had some of the most intimate conversations we’ve ever had but it’s taken years to get to that point and it’s really required not just doing the exercises with people but really setting the expectation for each new class that we’re going to get in there, we’re going to really dig in.  For example at the closing ceremony we asked each member of the first graduating class to share a challenge they’d faced and I was really nervous about it because they could have shared challenges that were veiled “look how awesome I am” like “it was SO hard to raise a million dollars”.  But they actually dug in really deep and saw it as an opportunity to share with the [third class] finalists who were sitting in the audience, and also with their cohort fellows from the next class, about what is it like to be a fellow, and what is it like to go on an alternative path?  We talk about the 20’s life crisis and this is that time, but they really brought out personal challenges as well and it was awesome.  This is starting to build that culture.

Lisa: I think there’s a MetaLearning skill there.  I wonder what we might call it.  Maybe Looking for Challenges or Noticing What’s Hard…I think it’s critical and that we don’t see it in our culture nearly enough.

D: We do something we call “Process work” and we get very focused with it.  For example at the last retreat we said, we’re going to go around and people are going to share what’s going well and something that’s a challenge.  I front-loaded the conversation with “You could make this a ‘look how awesome I am’ opportunity or you could use it as a chance to really let people know what’s going on…and it’s your choice.  I’m not here to force you, or to pull it out of you.  Or if you want you could pass.  Creating the space for that kind of conversation to occur…Maybe it’s the skill of Being Vulnerable.

[Check out TedTalk on Vulnerability].

Lisa: How has your approach to the Thiel Under 20 community changed?  What have you learned about being a leader and about how people learn?

Danielle: One of the biggest learnings that’s come out is that even self-directed people benefit from modeling and clear expectations, and it’s even better if the modeling and the expectations is as explicit as possible.  For example, this year was the first year we had a fellowship handbook.  It’s given people some sense of direction.

Also this year we wrote a Manifesto which has been really helpful and has allowed us to be on the same page as a community.  Of course with a program that is about doing your own thing there’s a tricky balance…balancing autonomy and togetherness.  But community is really important so while some people love being part of a larger group, other people want to do it on their own.  But ultimately we are a community.

This year we experimented with starting the class of with a common shared living space where they could land for the first few months of the program and it was a great experience.  They started doing things together.  We noticed that, after having the summer house, more of the third class have decided to live together and a number of them collaborate on projects.  And that’s what we want…we want it to be a more dynamic program.  Even for those people who didn’t join the shared living community, the ones who are living on their own, we really try to talk with them about building a community for themselves.  Even just having one friend or trusted person or mentor to have those vulnerable conversations with, that can help.

In my personal life and my couple relationship we have reflection time.  Our partnership frame is that even if something doesn’t directly affect him then if I’m unhappy and frustrated then it’s going to affect him.  So we have a specific time set aside so we sit down, reflect together and talk through challenges.  There’s a container for it.  A framework.

We are looking at how to support our mentors in building this kind of conversation and looking at how to model it for mentors.  When you have someone that’s more experienced and they’re willing to be vulnerable sometimes it’s easier to take part in those conversations.

One of things that one of our mentors said years ago was when you go out to a networking event try to find a way to contribute to someone there.  Ask about life, ask about personal stuff (especially romance) being able to have those conversations and the toolset to ask the fellow how it was going person-to-person was a great starting point suggestion.  Then you can get into the business stuff because getting-stuff-done and getting concrete and nitty-gritty with people is important but I think there are certain questions that can help mentors lead into conversations that might be a little sticky without it feeling really awkward.  Having a structure for a mentor meetings could be effective.  If they asked things like: What do you most want to get out of the meeting with me?

And we can put it out to the Mentee, too by telling them, here is a potential mentor conversation and you might be asked these questions.  AND you can also use them on yourself…or with each other.  This is a guided conversation for how to bring out the hard stuff.

Lisa: One of things that occurs to me is that some of the NVC questions could be built into a mentoring conversation.  And those could be given to the mentors, too. Questions like “What do you value?” Or “what are your most important needs and how can you get them met?” could also be really useful.

Danielle: Yes!  When I meet with new Mentors I might even do this process with them, on them.  Even without telling them what I’m doing. Often I like to dig into that kind of conversation.  But then we can make it explicit.  We could tell them, hey, this is what a mentoring conversation can look like; it doesn’t always have to look like this but this is an example of what we’re going for…that’s the level we’re looking for.

Lisa: I think when you build it into a system and make it cultural knowledge it can have that memetic quality.

Danielle: Yes, and it’s nice when you’re leading a community to have something to point to.  So that it feels more objective and they know that we’ve really thought about mentor conversations and we’re giving them the download.  We’ve always said that the alum classes are going to be the best mentors and if we can get them well-versed in these types of conversations early on it will be really helpful.

Lisa: What has been the cultural approach to integrating the alum class(es)?

Right now the alums are invited to pretty much everything.  We have workshops about every 6 weeks and they’re invited to those.  They’re invited to the retreat and the fellow socials etc.  We are trying to keep them integrated and we’ve always done things as a group and we want to keep them engaged that way.  I have some alums asking how they can help and I tell them just to reach out.

There’s a nice thing about an alum group is that the alums are TRULY on their own and 100% free to get involved.  For some of them the more freedom they have the more they embrace being involved.  We try to do that with the fellows, too, even though sometimes we do all have to get together because we have such limited time together.  Also, we’re here for the long haul and so we know (even though things have changed over time) we know the course we’re going.  There’s a different level of investment and organization development.

We do something with the fellows we call paying your dues.  We tell them that 300+ days out of the year they are free to do what they want but there are a few times in the year we are asking them to come together because it’s really important to have the whole group together.  Those days and events are what we call Paying Your Dues. That means we consider it important and if you have something you decide is more critical then it’s your choice.  The idea behind it is not punitive but rather we’re saying “we see this as important for your experience or for the community and if you choose something else as more important such that you miss it or you are late then you just Pay Your Dues”.  They can see it as making a conscious decision or they can choose to see it as a punishment but either way I no longer have to be the “disapproving parent”.  They’ve made a choice.  

Lisa:  Perfect.  This is an example of scaffolding as I see it.  Ultimately we want self-directed learners to do all the important things of their own accord but until they are ready to do it all on their own, it’s our job as mentors to help them.    With my own kids, I give them lots of opportunities and I give it to them without expecting anything other than they make good use of the opportunities and recognize the value provided.  I pay for those opportunities for them unless I see that they don’t make good use of it, like they are late to a class or don’t do the work requested of them.  In that case, they pay for the unused opportunity.  So, if they are late, they pay for the minutes they missed.   

There one more thing I’d like to add to your MetaLearning Skill set list and that is Approaching Life as a set of Experiments.

This comes up with young people I talk to who want to do something alternative but they don’t know how to frame it for authority figures in their life, like parents or teachers.  I met with a young woman yesterday who wants to come out to the Bay area and do an internship.  We talked about treating it like an experiment.  For example, you have your hypothesis (I think going out there I’ll build a better network, I’ll get experience in a new field, I’ll get to see a new part of the country) and a plan AND an end cap.  You might frame it like “this is a 3 month experiment and at the end of the 3 months I’ll get together with people I trust to evaluate how it went, and whether I would do something different next time?”

I’ve used this framework with parents too who want to do independent education but are worried they’re not ready.  And I’ll say “that’s cool, I’d be afraid if you were completely sure of everything”.  So why don’t you try an experiment.  You could do it for one quarter and see what happens and after the evaluation stage you can decide as a group if it’s working or not, or if it needs tweaking.  And you can always go back to school if you decide it’s not working.  That framework has been really helpful with lots of people.  Viewing life as a series of experiments but it takes having that reflective piece at the end.

Lisa: That really does bring us full circle in a beautiful way.  Danielle, thank you so much for your time and all that you do to further young people achieving excellence and contribution.