June 27, 2024
Listen to our new podcast episode with host Maryam Nizam of the Daybreak Podcast!
For this podcast episode, we had the pleasure of joining host Maryam Nizam on the Daybreak podcast, where we delved into the life changing power of connection with others. Our founder shared her story of transitioning from a prosecutor to a startup founder, driven by the question from her mentor, "What am I doing today that really matters in 100 years?"
In this episode, we covered key topics such as:
Tune in to hear more about Emily's journey and how you can find inspiration to make meaningful changes in your own life. Listen to the full episode now!
Links to the Episode:
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"Note: This transcript has been provided to improve accessibility for the hearing impaired. It has been edited for clarity and readability."
Maryam Nizam [00:00:00]:
Often we hit crossroads in our lives, not because of any major life event like a cancer diagnosis, the death of a loved one, a painful breakup, or being laid off from a job. Instead, it happens quietly. One day you're trotting along to a regular tune, and the next you're feeling disconnected with the music and need to switch playlists. And switching playlists, by the way, is big because we're creatures of habit and you want to be working out to the music that you know and trust. But you can only figure out your next favorite playlist by filtering through the many other options out there slowly, with an open mind and a willingness to experiment. On this week's episode of the Daybreak podcast, we’re talking to Emily Montgomery. Emily is a prosecutor turned civil litigator, turned private equity professional, and now a startup founder focused on empowering us all to be the highlight of someone's day.
Maryam Nizam [00:00:52]:
I invited Emily on because her journey of transition is one of a slow burn, a lot like mine. Nothing dramatic, just a deep awareness that her life didn't feel in alignment, so she should check in with herself and then explore. Emily's journey is a sign that anything is possible, irrespective of where your starting point is. And I know this is a message that so many of us unsure about our life direction need to hear. So join me in conversation with Emily Montgomery. Welcome to the Daybreak podcast. I'm your host, Maryam Nizam, and together we'll tune into stories, lessons and insights from everyday individuals on how they've navigated major crossroads in their lives. My goal is to inspire you with proof of what's possible and how to. Thrive when the tides of change come knocking. Because they almost always do.
Maryam Nizam [00:01:47]:
Emily, thank you so much for coming on today.
Emily Montgomery [00:01:49]:
Thank you for having me. I'm excited to be here.
Maryam Nizam [00:01:52]:
Yeah. I met Emily through a friend and her story is pretty close and connected to kind of the journey I've had. So I really want to interview Emily.
Maryam Nizam [00:02:01]:
So, Emily, let's get down to it.
Maryam Nizam [00:02:02]:
What's the biggest thing that's been driving you to change aspects of your life over the last few years?
Emily Montgomery [00:02:08]:
I think it's a teaching from one of my mentors. It’s “what are you doing today that will really matter in 100 years?”
Maryam Nizam [00:02:16]:
And so why don't you tell me about some of the things that you've done to answer those questions?
Emily Montgomery [00:02:22]:
Yeah, that's a big one, right? So I was about 28 and I had this wonderful revelation that I didn't do anything to cause or deserve. It's like one of those moments that I will remember and there's a before and there's an after. I had this realization that this is not my life.
Maryam Nizam [00:02:44]:
Okay.
Emily Montgomery [00:02:44]:
And I decided to change everything. I started really small at the time. I was in a really horrible relationship. I was a prosecutor, I was a lawyer, I graduated from law school. I was successful on the outside, and yet on the inside I felt like I was living somebody else's life and I was certainly not living my own. So I checked myself into a hotel, checked in with myself, made sure that that was the truth, I guess.
Maryam Nizam [00:03:16]:
So when you say hotel like, you literally mean a hotel, not like a therapist.
Emily Montgomery [00:03:20]:
No, like a hotel. I sipped lemonade by the pool.
Maryam Nizam [00:03:25]:
Did you do that because partly you felt like you needed a change of environment to help clarify things a little bit and give you the opportunity to extract yourself from where you were? New environment, new way of thinking, or a new perspective?
Emily Montgomery [00:03:38]:
Yeah. I mean, it was just two days, but I really needed time alone to check in with myself and not be around other people. I remember parts of that weekend, like they’re yesterday and it's over twelve years ago now, at this point.
Emily Montgomery [00:03:57]:
It was really just sort of a grounding check in. I heard this sort of still small voice. The check in was like, okay, is this what I am going to follow? I started really small. I really just started going to therapy once a week and asking myself in small ways, who am I right now? and who do I want to be? and what do I have to do to get there?
Maryam Nizam [00:04:24]:
Now that you've been through this, and you said it's been twelve years since, do you think a lot of people ask themselves those questions, and answer them honestly?
Emily Montgomery [00:04:35]:
I do. I think they do.
Emily Montgomery [00:04:37]:
I know that because people have a tendency to come to me and ask those sorts of questions. And it's always really interesting and sort of precious conversation when people are starting to explore “am I in charge of my life?” and “do I like myself?” and “do I like my life?”
Maryam Nizam [00:04:56]:
Okay, we'll come back to that in a bit. You basically said you went to therapy and that kind of set things off. From therapy, you went from being a lawyer to working at a private equity firm. So you switched up your career.
Maryam Nizam [00:05:11]:
But from there, did that give you peace?
Emily Montgomery [00:05:14]:
Some, yeah. And I think the transition happened a little more slowly. This is over a period of, what, four years or more? I spent two years as a prosecutor first. I left that. I became a civil defense litigator. I did that for a while. I can't remember exactly. I don't know, at least three years, maybe five, possibly.
Emily Montgomery [00:05:44]:
I wasn't unhappy. It was that I felt like there were parts in me that were atrophying. Like my creativity, my drive to want to do things, was atrophying. It was a lot of research behind a computer interspersed with people calling to yell at me.
Maryam Nizam [00:06:09]:
So it's just wonderful for your ego.
Emily Montgomery [00:06:13]:
I felt like there was probably something out there where I could be more useful, and I guess feel more fulfilled by using my own inherent gifts. That's when I transitioned into the chief of staff role, and that was a lot of fun, actually. I did that for six years. It was a very dynamic role. I got to interact with a lot of people, and that really checked that creative box for me. I was able to put systems in place and move forward in a dynamic environment, if that makes sense.
Maryam Nizam [00:06:57]:
Yep, that makes sense.
Maryam Nizam [00:07:00]:
Switching that up was great for you. You obviously got to expand your horizons. I'm sure that that kind of change from being a prosecutor, doing something that you've been trained to, to just stepping into this new space, what kind of fears and doubts did it come with?
Emily Montgomery [00:07:16]:
Quite a few doubts, I would say. For about nine months, I only had energy to work.
Emily Montgomery [00:07:25]:
It was so exhausting because people were talking to me in a language I didn't understand. They were talking to me in financial and investing terms, and it was like speaking to me in Russian.
Emily Montgomery [00:07:37]:
I could feel that part of my brain expanding to learn all of these different terms and to learn the environment, to learn business. I basically got an on the job MBA. I sort of just gave myself permission to be really lazy and be more insular.
Emily Montgomery [00:07:58]:
I wasn't doing a lot of stuff on the weekend because I didn't have the energy. I knew that that transition was important, and so I gave it.
Maryam Nizam [00:08:05]:
And when you take on a new venture, you kind of have to at the start, number one, it's engaging. And number two, you sort of have to give yourself the runway and the investment to build yourself that makes a whole lot of sense. Six years on, though you've taken a different path. Maybe you can tell me about that. And Emily is full of stepping stones, of just transition. It's great.
Emily Montgomery [00:08:30]:
I really feel like I've gone on a path of sort of becoming more myself as I've aged. You could not pay me enough to be a teenager, like, in my twenties again, really. Because now I'm just so much more in tune with who I am. In 2022, I started taking care of my dad, who was diagnosed with Alzheimer's. It really started putting me in perspective of death, really, and dying.
Emily Montgomery [00:08:58]:
And life is short. So I really started asking myself those kinds of questions. Like, what am I doing today that really matters in 100 years? Am I living to my fullest potential? Am I creating, really, in the ways that I need to and want to? So I made the decision to take a sabbatical.
Emily Montgomery [00:09:18]:
I decided to walk across Spain on the Camino de Santiago. That was really the start of that transition. That, of course, is its own full story.
Maryam Nizam [00:09:30]:
So the Camino de Santiago is a walk through Spain, Italy and France, if I'm correct. And you're just hiking daily, but you can join parts of that hike and drop off as necessary?.
Emily Montgomery [00:09:41]:
There's different routes. There's at least ten different routes that you can get to this one place. So I took the Francisco, the traditional, the OG kind of path. It starts in France and then goes along the top of Spain. I went to Santiago and then all the way to the ocean.
Maryam Nizam [00:09:58]:
And so you did this all on your own?
Emily Montgomery [00:10:00]:
I did. I made friends along the way. But, yeah, I was primarily alone.
Maryam Nizam [00:10:05]:
So I suppose as a lawyer, you're working intensely long hours. A lot of it is just on your own. You come to be in private equity as a chief of staff.
Maryam Nizam [00:10:15]:
Again, there's teamwork involved, but there's also a lot of strategizing that you sit down and you figure out by yourself and being on your own. You said you spent your weekends on your own, too. You were so exhausted in the first year. So all of that is not unusual for you by all means.
Maryam Nizam [00:10:29]:
But what did being alone on this journey elicit for you?
Emily Montgomery [00:10:35]:
That's a good question.
Emily Montgomery [00:10:37]:
I would say I was physically alone, but I was not emotionally alone. Does that make sense? I was lucky enough at the time to be a part of this group that I had joined in Boulder, and they had put together this beautiful ceremony sending me off
Emily Montgomery [00:10:53]:
I had recorded all of these messages from them. So whenever I felt alone or felt like I was struggling, I was able to listen to all of these audio notes along the way, and so I never felt alone.
Emily Montgomery [00:11:09]:
Does that make sense? Like, you can be alone but not lonely.
Maryam Nizam [00:11:13]:
You can be with many people and still be alone..
Maryam Nizam [00:11:15]:
It makes sense. Whatever gives you that common feeling of connectedness, and different people are energized in different ways. So you did Camino de Santiago. How long did you do that for?
Emily Montgomery [00:11:29]:
Exactly 40 days.
Maryam Nizam [00:11:31]:
Okay, so 40 days on. What was your learning? What did you come away with?
Emily Montgomery [00:11:35]:
I learned so many things. That's really hard to narrow it down. I will say I've been amazed by the number of the friends that I made there. So many of them have created products and released albums. The art and inspiration that comes along the journey is really interesting. There's a sort of magical quality to it.
Emily Montgomery [00:11:55]:
My takeaway from the journey was really where I started creating this app that I've since released, and I have all these voice notes of me sort of thinking about different strategies.
Emily Montgomery [00:12:13]:
I named it there. I have a voice note of me naming it. So that was a big product. I guess there are many takeaways.
Maryam Nizam [00:12:20]:
Emily had this aha moment, took a sabbatical, went off to Camino de Santiago, and came back and basically decided to change careers again. And that's where your app came to being. So why don't you tell us a Little bit about the app?
Emily Montgomery [00:12:35]:
Yeah, I'm happy to.
Emily Montgomery [00:12:36]:
It’s called HiLU, which is short for hi, I love you. It helps people record and collect words of affirmation and gratitude to others throughout their lives.
Emily Montgomery [00:12:49]:
When people think about a voicemail from a loved one that they have, they connect to it pretty easily. But it's really about starting and cultivating that practice of regularly affirming others and telling them what they mean to you now, as opposed to waiting for a eulogy.
Maryam Nizam [00:13:06]:
That's cool, because I think there's always moments where we're like, God, there's so much left unsaid. When you think about it at that moment, you have these great thoughts. But if you're waiting to say that in person, it may never happen. It may never come out in the original form that you intended it to. So I think that's really cool. You came to this during the Camino de Santiago, but was there something else that inspired you along the way in terms of getting to this particular idea?
Emily Montgomery [00:13:34]:
There’s a series of events that happened along the way. I always say that my journey on the Camino started way before my actual journey. First you have to get there, right?
Emily Montgomery [00:13:49]:
You create that intent to get there, to start the journey, and then all these things start happening, like obstacles. One of the things that happened that really profoundly impacted me right before the journey was one of my mentors from my twenties passed away suddenly and unexpectedly. It really caused me to go into kind of a reflective mode, and a mentor that I was working with, still presently at the time, had a stroke one week into my journey. He was one of the people that I had had that voice memo from, and he was reciting to me a Robert Frost poem from memory and telling me that I was on the right path. That I was brave and wonderful. After he had the stroke, his words just took on this new meaning of encouragement to me to just keep going and be my biggest and bravest self.
Maryam Nizam [00:14:46]:
And you may have answered this, but I'm curious, what impact do you want this app to have on the rest of the world?
Emily Montgomery [00:14:52]:
My ultimate dream, really, is that everyone has the opportunity to hear from other people what their best attributes are. To hear those things repeatedly over time. That's really what I needed as a kid and in my twenties. I would love, ultimately, for people to be able to be more brave, be bigger, be their baddest selves as a result of knowing their highest qualities.
Maryam Nizam [00:15:20]:
And I'm with you on being bigger, brave and badder, because I think a lot of us hold back, mostly because of our own selves, not even because of the environment that we are in. But do you see any negatives to receiving so much positive feedback?
Maryam Nizam [00:15:34]:
Because I look at my nephews, who, even with the negative feedback, are like, we're the world, we own the world, and you are our servants.
Emily Montgomery [00:15:43]:
Uh huh. I think you're sort of speaking to narcissism and self centeredness.
Maryam Nizam [00:15:52]:
My nephews are younger, so they don't really necessarily count, but it does set a precedence over time.
Maryam Nizam [00:15:57]:
When you're so pumped up young, you kind of also may struggle to be more self aware of the things that may need a little bit of polishing and refinement in yourself. So, yes, the narcissism part, but also what's the right age to be this positive about something?
Emily Montgomery [00:16:14]:
That's a good question. I'm not sure I've thought about it from the lens of age
Emily Montgomery [00:16:16]:
I do know some of my friends are raising some of the most wonderful kids, and they don't hold back on the positive feedback or the words of affirmation. And I do think that there's something to the fact that if you give to the younger generation, for the most part, what I've seen is that they're inspired to also give and almost give earlier. Think about what their impact is earlier.
Emily Montgomery [00:16:34]:
And that's something that I really love about Gen Z, is they're all about their impact and what really matters. I think they have a lot to teach us in that regard.
Emily Montgomery [00:16:54]:
To sort of answer the narcissism point, it's a good one and I love this question.
Emily Montgomery [00:17:01]:
In my experience, the true narcissist is not really happy. I am not a psychologist, but I have done a lot of studying in this area. I think it comes from unmet needs.
Emily Montgomery [00:17:14]:
As a child, every narcissist you meet has an unhealed child within them. So I don't really withhold that sort of feedback from them either. One of the great things about my mentors that I've always been fascinated by is they have this almost transformative power to see the negative in somebody and know it. But you only interact with the positive parts of them. And by only interacting with the positive parts in them, you almost give them an opportunity to act from those parts.
Maryam Nizam [00:17:51]:
So that's interesting, because, actually, the question I was going to ask you was this: Sometimes people can hurt you, people can be negative towards you, and yet you would still choose to do the right thing.
Maryam Nizam [00:18:01]:
And when I mean the right thing, that would be to approach that person with humanity, respect, and joy in all the goodness that you have in you.
Maryam Nizam [00:18:08]:
I believe that you do that for you more than you do that for themselves, because that enables you to be true to yourself. And so the question I have about this app is, when somebody is giving positive feedback, who do you think benefits more from it? The person who receives it or the person who gives it?
Emily Montgomery [00:18:25]:
That's a great question. The answer is both, and neither. It can be equal
Emily Montgomery [00:18:29]:
And actually, the benefits of giving positive feedback are many.
Emily Montgomery [00:18:39]:
It kind of taps into our need to volunteer, and get involved in a cause larger than ourselves. It makes us feel great, and it doesn't matter really what the reaction is. I would also say that when you're in a practice and a habit of giving positive feedback, you may not always hear back from people. And that's also okay.
Emily Montgomery [00:19:01]:
Some of the most impactful statements that I was lucky enough to receive, I didn't really fully take them in or appreciate them until 5, or 10 years later. Yet here I am, still talking about them, and I'm not sure that I responded appropriately, even at the time. I may have been a little more stiff, or robotic, or just kind of wanted to get my work done.
Emily Montgomery [00:19:28]:
I think that's all okay. But there's a wonderful treasure trove of research on all of the benefits of proactive, active kindness to others.
Maryam Nizam [00:19:40]:
I'm with you on that. I think you grow just as much by undertaking some of these things in a positive and appreciative and loving mindset. So I'm with you on it.
Maryam Nizam [00:19:54]:
I guess in doing all of this, from moving from private equity to coming to build this app, you've had to give up a few things. Like a steady paycheck and potentially lost friends. You've made moves. Tell me about what it takes to do this and why you were still good with it.
Emily Montgomery [00:20:10]:
Well, I don't want to claim that I was so good with it. I think in one of your emails to me, you asked about the logic behind my moves, and a lot of my decisions are not really strongly logic based.
Emily Montgomery [00:20:26]:
I felt this still small voice that I felt compelled to listen to, and so I had to leap. I felt compelled to leap. It wasn't like I sat there with this rational choice. I did not weigh the pros and cons. I just learned to leap.
Emily Montgomery [00:20:42]:
It can be a very lonely journey. I did lose friends. Every time I made one of these sorts of massive leaps, I lost my identity. I lost a lot of what was comfortable to me.
Emily Montgomery [00:20:59]:
Most recently, leaving the chief of staff job, I had some semblance of power, autonomy, authority. It's almost like a whole dress that I put on in the morning. And that was my identity. That was who I was.
Emily Montgomery [00:21:12]:
I knew who that person was and how she moved in the world to become a startup founder. I'm still learning that. Like, who am I now? How do I talk? How do I dress? It's almost like everything gets rewritten.
Emily Montgomery [00:21:25]:
I still carry with me all of my past learnings. It is by taking the leap that you learn so much about yourself and what doesn't change.
Maryam Nizam [00:21:37]:
I'm wishing you tons of luck with this app. It'll bring joy to people.
Maryam Nizam [00:21:41]:
I think there's a shortage of joy. I just spoke to somebody who said one of the biggest things that's lacking in the world right now, and that's diminishing, is human interaction. While this (HiLU) isn't necessarily getting you to that level of human interaction, that in person interaction, I think it still does create a moment and probably an easy way for people to connect.
Maryam Nizam [00:22:01]:
You don't need to have a full conversation, but at least you're able to share in that moment what your thoughts are. So I'm all for it
Maryam Nizam [00:22:09]:
Emily, you talk about this being a lonely journey, and we've talked about this before. You give a lot to each of your careers, you're single. You're trying to figure out not just what your purpose is, but also who and where you fit in and everything. And so my understanding is that you're Looking for an almost alternative way of living.
Maryam Nizam [00:22:33]:
So can you tell me about your other journey of what you're thinking, and how you want to live your life so that you might feel connected?
Emily Montgomery [00:22:46]:
I have shared a beginning inclination that I think that the way that we all live in these single family homes and apartments and little enclosures is not good for us, full stop.
Emily Montgomery [00:23:01]:
It's not in alignment with how we are biologically wired. We are designed to be in community. I see a lot of people doing all of the nutrition and the gym, the workout, the ice baths, the supplements.
Emily Montgomery [00:23:17]:
But, you know, loneliness can increase your risk of dementia by 50%. It increases your risk of all cause mortality by 26%. It's equivalent to smoking 15 cigarettes a day. That's from the surgeon general's report last year and that really brings what could be called a mental health crisis into physicality and into our longevity. I think that should really pique people's attention.
Emily Montgomery [00:23:45]:
What are we doing to combat that? For me personally, I can feel the ways in which living alone is not ideal and sort of my long term pie in the sky dream. I don't know how far off this is, but I would love to live in a place where all of my friends have a parcel of land and we have a communal space where we can kind of gather. Maybe have a gym, a community table and a kitchen so we have our away space and our independent space, and we also have a place to gather. So that's sort of a dream at this point.
Maryam Nizam [00:24:28]:
Honestly, like, number one, it might be a dream to you, but it's not a dream. It's a reality in so many places where people are starting to feel disconnected and disengaged living the life we’ve traditionally lived for a little while. So they're building their own communities.
Maryam Nizam [00:24:47]:
It might come together around things like we want access to pure food, or they might say, you know what? we're going to come together from a religious standpoint because we want to raise our kids in a specific way and this is the community we want to give them. It's not unusual. People are coming at this from a perspective of feeling alienated and isolated, and I asked you this because for the longest time, I felt a bit weird about being single, almost 40 woman living in a metropolitan city, wanting some more of that.
Maryam Nizam [00:25:13]:
Because being in my condo alone, I've had some of my hardest nights and I've done them all on my own. I wish I could have walked over to a neighbor and said, hey, would you be free for a tea or coffee? But it's so weird, right? People think it's weird in Toronto when you talk to strangers. Why would you knock on your neighbors? I've been playing around with that idea and trying to figure out where I would fit in so I'm glad to know that I'm not the only one. I also wanted to kind of talk about it and share it as a perspective. So thank you for sharing, and I hope that you find something that fits you, and maybe we'll have a different and separate conversation about this at another time that's a bit more focused.
Maryam Nizam [00:25:54]:
Emily, before we end, what do you believe about people who are at crossroads in their lives? We talked about this a little bit at the start where you said a lot of people are coming to you with those questions, but how many of those people make changes in their lives? What are those barriers?
Emily Montgomery [00:26:08]:
I think if you're at a crossroads, you are in the best place. You have a world of possibilities in front of you. I would say not all change has to be external. You don't have to change your job, you don't have to change where you live, you can make changes internally and shift your perspective. Shift the way in which you're thinking about your life. You can actually just shift your narrative and make new stories about who you are and what meaning your life has so I would remove the pressure of I have to change the outside. You don't, necessarily. You can change the inside first and see what happens.
Maryam Nizam [00:26:55]:
Well, thank you for your time, Emily. I love chatting with you. For anyone who's interested, Emily, what's the instagram handle for your social media handle for HiLU?
Emily Montgomery [00:27:04]:
The socials are @teamhilu and the website is teamhilu.com.
Maryam Nizam [00:27:08]:
Okay, so I'm gonna put that down on the podcast description and I hope everybody follows and tunes in and see where Emily's journey goes.
Maryam Nizam [00:27:15]:
But Emily, thank you for sharing.
Emily Montgomery [00:27:17]:
Thank you so much for having me. It was a great conversation.
Maryam Nizam [00:27:21]:
Immediately prior to recording this conversation with Emily, I just got off a rather difficult and exhausting call, so my energy was low. When I shared this with Emily, her face lit up as she suggested a short session of bioenergetic exercises to release my tensions. So through my computer screen, I mirrored Emily as she proceeded through hand and breathing movements that really did the job and set the stage for a fun and warm conversation. A small action, but such a massive impact to my mood and my ability to engage in our conversation wholly. That's the theme of Emily's entire small actions. Checking into a hotel room to give her the space and environment to check in with herself, therapy to get herself on a path to reflect on the real her moving jobs and yet staying within the same industry as opposed to immediately making a big, completely different transition. A sabbatical incident, quitting, and finally a calm hike through the Camino de Santiago to immerse herself in the simplicity and beauty of the natural world and continue her self discovery and path to positivity.
Maryam Nizam [00:28:25]:
You don't exactly think of a lawyer and prosecutor as a prime candidate for creating an app titled Hi, I love you, but that's where Emily's now ended up after finding value, inspiration, and comfort and voice notes people put together for her as she ventured off on the Camino de Santiago. In the process of Emily's journey to becoming more of herself, irrespective of how gradual it was, she too has lost pieces of her identity, friend groups, power, autonomy and all that was comfortable to her. Transformations inherently are lots of guts before they are glory, but make the change anyway. And while you're doing it, be kind. Be kind to others. You never know the impact your words and actions may have on a soul secretly in need. And be kind to yourself, because reflecting, acknowledging and undertaking change is one of the bravest things you will do. And it's one of the best places to be because you have a world of possibilities in front of you.
Maryam Nizam [00:29:23]:
As we come to a close, taking a page out of Emily's book, I want to say to all of you, hi and I love you and thank you for listening. And now that you've taken a break, let's go explore. Until next time, live strong and embrace day break.
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