I’m Amy and I’m 56. I’ve had a long and twisty career with some distinct chapters within it. The first chapter was very corporate and then increasingly the arc has been towards smaller, more nimble and innovative companies. Ultimately, I started turning into new areas that align more with my values, starting with baby steps and then a gigantic leap (I am now the co-founder and CEO of a startup, a mobile app, called Daily Haloha.). Against that backdrop, my personal life has been demanding and complicated and has always been a really important consideration for me in my career choices.
I have three children, two millennials and a gen Z’er. I separated from my husband when my children were small. I have twins, and my children were eight, eight, and three years old when I became a single mom – way ahead of the curve! It was complicated balancing family life and career as a solo (in many regards) parent. Many of my career choices had to explicitly consider how it all fits together and how to be in service to my family and my financial needs and my own career aspirations.
Now I’m in a new place where I’ve got three fully launched children, the final one as of this summer as my third and final graduated from college. So it’s a really different position to be in.
Launching the Daily Haloha app this year has been by far the biggest pivot and reinvention in my career. I founded this startup in my early 50s, just a couple of years ago. It was completely unexpected. I was not searching for a reinvention and certainly not searching for an opportunity to be an entrepreneur. It happened because I had an inspiration to address a problem in the world that affects me deeply and is so anathema to my own sensibilities that when I thought I had a glimmer of a solution, I felt I had no choice but to see if I could bring something healing into the world.
Daily Haloha is a mobile app that serves up a moment of simultaneous reflection and connection. The experience originates every day with a single thought-provoking fill-in-the-blank question that I pose to the world. That question tees up a simple experience for folks starting with reflecting on that question. They think about what’s true for them. They answer it authentically and maybe even vulnerably. And they’re invited to do so because we have three deeply held principles about our app: it’s anonymous, it’s completely free of judgment, and it’s free of a popularity or status contest.
Those values are deeply embedded in our ethos. I think it invites people to really show up as themselves and feel like they belong, just as they truly are. So, they answer the question and then they send off their response. Their response gets delivered randomly and anonymously to one other community member in the app. And then they immediately get one back from someone else in the world. That exchange is meant to be a moment of reciprocity and feeling heard by another human on the planet.
Then when the participant has a moment to reflect on what they received back, they apply a [non-judgmental] reaction sticker meant to acknowledge to the sender that they were indeed heard. And then the third and final step of the daily flow is to look at our Haloha wall and see all of the responses that are trickling in throughout the day. It’s a chance to get perspective from others who may not have expressed things the same way or had the same experiences or even view the world the same way.
I have to say I am moved every day by reading these responses on the wall. They’re full of humanity. They’re these little bits of hopes and dreams and regrets and humor and all these things that we share as humans. While the daily flow is a simple and light experience we have a very big intention – and that intention is to rekindle a sense of shared humanity if not empathy.
It’s an experience that I hope, through routine usage, feeds into our personal wellbeing as we pause to reflect and express ourselves, and also our collective wellbeing as people get this spark of recognition for others and renewed affection for humanity.
What would you say has been the biggest shift after turning 40 (or 50)?
I’ve described the shift in my career focus, but it’s gone hand in hand with a big shift in how I see myself in the workplace as a leader and really in the world. That evolving self-concept was in part what drove me to make the leap to launching the startup. But launching the startup has accelerated the pace of change beyond what I could have imagined and resulted in even bigger shifts.
The shift that enabled me to take a risky leap into entrepreneurship was feeling a stronger and stronger pull to align my work with the things I care about most. I recognize that finding meaning in one’s work is a fairly common refrain for people in midlife and it was true for me. I had made smaller career movements toward purpose, and whenever I did, it was strongly validating. Over the past decade, the work I was doing increasingly solved real pain points for customers, and those customers were often underserved or marginalized in some way. As this shift was happening I had the realization that I felt better, more motivated, and more energized. And perhaps that emboldened me to take this leap into a startup that’s 100% aligned with my values of empathy and belonging and also 100% scary!
But here’s the part that completely took me by surprise and that I’m still grappling with – the discomfort of being my own boss. There’s the discomfort of having a startup and not knowing what I’m doing much of the time. And I kind of expected that. I feel like I’m laying down the track the second before the train barrels over it most days: Mad googling, reach out, find resources, find advisors, find expertise, figure it out, make a decision, put it in place. It’s this constant process of figuring it out just in time and it’s very uncomfortable. But I think that this is where midlife is a beautiful thing because I know that I’ve solved problems before. Everything is solvable. Everything has a solution. I can make decisions with imperfect information. It’s going to be okay.
I expected that discomfort and I have the confidence to deal with that discomfort. The part that I didn’t expect is how it would feel not having anyone telling me I’m doing a good job. There’s nobody to say, “I know that was hard. You put in a really big effort. I commend you. Good job. Here’s a little advice. Tomorrow will be easier.” I had always gotten that validation either from my boss or from a client, or even from my team. All of a sudden no one was telling me any of that. I really missed that external validation. I didn’t know how to celebrate my successes or show affection to myself for the work I was doing. I was doing work I loved but somehow, I was feeling this little bit of emptiness. It was really a struggle and it took me awhile to even put a name to it.
Now I realize how hooked I was on feedback and acknowledgement and affirmation. So I’m working at being my own cheerleader and making sure I’m connecting with people that lift me up when I need it.
When do you feel you are most powerful?
I feel most powerful when I’m in conversation with others and we’re sharing ideas and when something I’ve said or feel or believe lights a fire under somebody else. They might see themselves reflected in what I’m saying, or I’ve been able to connect the dots in a way that sparks something for them. It’s the power that comes with this particular alchemy of ideas and expression where we’re all enriched and lit up by the conversation. There’s nothing that feels so magical to me as that moment. And it feels like power. It feels like power because it feels like it has the energy to create something new and ripple through the world.
What are the top 3 most important things to you right now?
Like many, I’m really troubled by the tribalism and the “othering” that’s going on in the world. There’s so much data around that and how it has both given rise to authoritarianism and been a result of it. Relatedly, what also keeps me up at night is the growing epidemic of loneliness and social anxiety, status anxiety and other mental health challenges related to the constant conflict and comparison rampant in the world and accelerated by social media. These things trouble me so deeply not only because I believe so fundamentally that everybody matters and everyone belongs equally but also because of the real danger when fear replaces hope and love.
So inclusion, belonging, and empathy feel very important to me right now. Daily Haloha has had a very unexpected benefit in my life, which is the “permission” to dive deeper into these topics. I’ve always cared about these things both as values and areas of study, but I never gave myself the permission to research or read about these topics because it was neither in service to my family or in service to my career and if it wasn’t in one of those two buckets, it took a back seat for a very long time.
But now, because my business hopes to address those things directly, all of a sudden I have all the permission in the world to pursue these topics and it’s so lovely. I can read something for a couple of hours where I never would have taken the time to delve into an academic white paper on these subjects. I have learned so much. I’ve also gotten involved in organizations that are like minded, expanding my world even further
For example, I now volunteer for Sidewalk Talk, a community listening project. I participate in other projects that are about listening across divides and I’ve connected up with people, organizations and initiatives that care about empathy and belonging and listening and helping everyone be seen. And it’s just been such a profound blessing.
How do you make sure your actions are aligned with what’s most important to you?
That’s a fantastic question and a really relevant question because now that our app has launched I have to figure out the business side of what we’re trying to do. There’s some tension between my purpose and intention with the app and becoming a sustainable economic proposition.
These tensions require innovative thinking about our business model and extensions of our app platform. For example, I mentioned our app’s deeply embedded principles: that it’s anonymous, free of judgment, free of popularity contests. But there are other values we hold such as we are not going to engineer your attention. We’re not going to sell your eyeballs to the highest bidder. We are committed to doing things differently than the social media model that has sold our attention, escalated our social anxieties, accelerated tribalism, and offered judgment at every turn. They do those things because preying on our vulnerability and our worst human instincts makes money.
It’s quite challenging to figure out our business model and stay true to our principles. But we are up for the challenge!
And it’s really interesting because I’m getting a lot of feedback from our app users now and many of them are asking for certain features that are really common in social media but aren’t necessarily good for one’s wellbeing.
So there’s tension not only with the business model, but within my customer requests. I’m trying to understand whether the requests are because we are so conditioned by social media that it’s natural to expect or look for some of the same features in Daily Haloha, or, if there’s an underlying human impulse here that’s actually quite altruistic that I want to give expression to, but maybe in a different way.
We are exploring all of these tensions both from the business economic side and also from the customer side.
To answer your question, how do I stay true? I keep our values in the forefront of my mind, and they’re also written down. They’re documented for me and for everyone that works with me on the team, my business partners, and my vendors.
And I talk about them publicly, which also holds me accountable and the business accountable to our values.
What seeds are you planting today for the future?
My vision for Daily Haloha is so vast. I hope I have the opportunity to make Daily Haloha my future and perhaps my only future from a career standpoint. I have a lot of things to figure out in order for the business to be a viable future for me. But my imagination around it is endless. I feel like we’re taking baby steps, and planting seeds, every day to figure out what we’ve got, what we don’t have, where we need to enhance or pivot or re-imagine so that Daily Haloha takes root and blossoms.
The other way I’ll answer that question is to bring in my personal life. My twins are now 26 and my baby is 22. I’m starting to get excited about imagining their future lives and families. I have a wonderful partner of long standing. We’re actually about to sell our house and downsize and we’re planting seeds for a different personal life, one less encumbered by possessions and household demands.
So as much as I focus on my career and am planting seeds for hopefully a long runway of working on Daily Haloha, I’m also planting seeds for a different lifestyle where I’m opening up more possibility to be nimble with my family and with my relationships. And the one thing I really need to figure out is how to integrate those because as a founder of a startup, I’m working 24/7. I’m sowing some seeds for a less encumbered lifestyle but it might be a while before those seeds can sprout into true flexibility. I don’t yet know how, or more accurately when, it will all come together with a work-life integration that feels balanced and sustainable.
What advice would you give someone who is interested in redesigning midlife?
So many things I can say here! It’s going to sound a little trite, but I think there’s no substitute for self-knowledge and I think for me personally, one of the things that’s enabled me to make this pivot and then leap into some new territory is to become more acquainted with what lights me up, what my non-negotiables are, and all those things that I want and need in a workplace where I can thrive and flourish personally.
I wish I had sought expert advice earlier because we only know what we know about ourselves and we tell ourselves a lot of stories that are hard to unwind without being challenged by someone else. The advice I would give is don’t short change your own journey of personal exploration and growth and understanding yourself because it’s really hard to make good decisions without doing that work. The process of self-knowledge requires, I think, trying on a lot of things and getting uncomfortable. Honoring that process and getting some guidance, whether it’s from your personal board of advisors or from a professional coach or mentor is invaluable.
It’s also a good time to check in with your relationship to external validation and challenge yourself to be more inwardly directed.
How can people connect with you and your work?
In so many ways! First, download the app and give it a spin!
I’d love to hear from people who have feedback or suggestions for the app or want to discuss collaborations or partnerships. I’m also happy to be a resource to other aspiring entrepreneurs. My email is firstname.lastname@example.org. If you send feedback via our website or from within the app, it also lands in my inbox. I’m also a very avid LinkedIn user, so connect with me on LinkedIn.