4 months ago, I woke up one day and decided to start a mentorship circle with a small group of talented, high-potential female designers.
It was the most amazing experience. Here's a thread on what I learned
It was the most amazing experience. Here's a thread on what I learned

Some background first—in my own career, I came to the benefits of mentorship late. I really struggled with asking for help. I saw it as a weakness.
This is a fallacy many folks with imposter syndrome believe. We like the idea of "mentorship", but not "exposing vulnerabilities."
This is a fallacy many folks with imposter syndrome believe. We like the idea of "mentorship", but not "exposing vulnerabilities."
To have a mentor truly help you, three things need to be true:
1) You have to know when to ask for help and what specifically you need help with,
2) You have to be willing to honestly share your dreams
3) You have to be willing to honestly share your worries
1) You have to know when to ask for help and what specifically you need help with,
2) You have to be willing to honestly share your dreams
3) You have to be willing to honestly share your worries
It does not work for you to say "Can you be my mentor?" or "I want my career to be X, can you help me?" That is too vague.
What's getting in your way? What specifically can I do for you? How do I know if I'm even the right person?
It can't be my job to discern what you need.
What's getting in your way? What specifically can I do for you? How do I know if I'm even the right person?
It can't be my job to discern what you need.
(Btw: mentors don't need to be more senior than you. Clearly folks who have gone through your same experience in the past are helpful. But think of your peers. Can one of them give you useful advice on something you're struggling with? Depends on problem, but often YES!)
So my goal with this mentorship circle (which we called, very innovatively, D. Circle) was to make it a safe place to ask for help as well as discuss everyone's dreams and worries.
My assumptions were:
1) Safety and trust takes time to develop, so let's make this 7 sessions and require full commitment in showing up.
2) A loosely structured agenda, pre-reflection, and asking the right questions makes it easier to go deep into topics
3) ....
1) Safety and trust takes time to develop, so let's make this 7 sessions and require full commitment in showing up.
2) A loosely structured agenda, pre-reflection, and asking the right questions makes it easier to go deep into topics
3) ....

3) It's hard to sustain a dream if it doesn't seem achievable, and something doesn't seem achievable if you don't know the path
4) The more we know about someone's story, and the more their story resembles ours, the better we can help them
4) The more we know about someone's story, and the more their story resembles ours, the better we can help them
I decided to create the group based on an application process that helped me understand 4) above. It was a pretty involved application, as you can see here: https://airtable.com/shr1T17d3atdpbMSA
Expecting maybe 20-50 applications, I put this out on Twitter and got over 350 from incredible designers all over the world. It was an extremely difficult task of selecting 8! Especially since so many shared with me their honest struggles.
In the end, I prioritized based on who I thought would benefit the most from the program. It's been a huge privilege to get to know and see the talents of @Noella_Dias, @LooooisYang, @susansoeun, @yinie0613, @e_see, @mala_panda, @mirdhaaakanksha and @TaylerAitken over the months!
One thing I loved was how we all co-created the curriculum together. We had a theme for each session, and everyone pitched in and helped vote on what those themes would be. We discovered that entrepreneurship and strategy ranked high on everyone's list, for example.
My role was simple:
1) Ask questions to help the group reflect on their dreams and worries for each topic
2) Share my own stories as it related to that topic as one example of a tangible path
3) Encourage everyone to discuss in small groups how to make their goals actionable
1) Ask questions to help the group reflect on their dreams and worries for each topic
2) Share my own stories as it related to that topic as one example of a tangible path
3) Encourage everyone to discuss in small groups how to make their goals actionable
I'm grateful to the ladies for sharing their feedback after each session! What worked the best for us was:
1) A good chunk of time spent in small-group discussions with on the topic
2) Personal stories about my own insecurities and mistakes related to each topic
3) ...
1) A good chunk of time spent in small-group discussions with on the topic
2) Personal stories about my own insecurities and mistakes related to each topic
3) ...

3) The "homework" aka reflection questions that everyone answered in a thread on Facebook Groups prior to each session
4) Getting input on what to focus on for each topic
4) Getting input on what to focus on for each topic
A normal session would be:
Pre-meeting: reflection questions homework
1) 5 min - unstructured catch up
2) 20-30 min - me sharing my experiences on the topic
3) 20-30 min - breakout rooms (4 ppl each) to discuss action plans in more depth
4) 5 min - closing
Ad-hoc 1:1 chats
Pre-meeting: reflection questions homework
1) 5 min - unstructured catch up
2) 20-30 min - me sharing my experiences on the topic
3) 20-30 min - breakout rooms (4 ppl each) to discuss action plans in more depth
4) 5 min - closing
Ad-hoc 1:1 chats
Our topics:
1: Introductions. What makes us awesome?
2: The confidence game.
3: Disagreeing/influencing/translating design
4: Strategic thinking
5: Entrepreneurship
6: Career conversations for the next 6 months
7: A guide to working with you
8: Supporting ourselves and others
1: Introductions. What makes us awesome?
2: The confidence game.
3: Disagreeing/influencing/translating design
4: Strategic thinking
5: Entrepreneurship
6: Career conversations for the next 6 months
7: A guide to working with you
8: Supporting ourselves and others
We met every two weeks over Zoom, and I found myself always excited about the meeting. Reading the reflection responses ahead of time was a huge highlight. And it was such a blast of energy to see everyone's faces and to talk together!
To close, I hope this thread inspires other people to consider mentorship, starting their own circles, or simply being more open to asking for help.
You don't have to do it like we did, you can do it any way that works for you.
You don't have to do it like we did, you can do it any way that works for you.
One of the great richnesses of life is our relationships.
There is so much that we gain from others; there is so much we can give as well.
There is so much that we gain from others; there is so much we can give as well.
(And feel free to share your own reflections and learnings, @Noella_Dias, @LooooisYang, @susansoeun, @yinie0613, @e_see, @mala_panda, @mirdhaaakanksha @TaylerAitken!)
