My Favourite Failure: Happiness expert who was desperately unhappy running a happiness startup - Jennifer Moss

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1:00I kept going because I didn't recognize it but it was a point where I was so unwell and there were so much I think a delta between what my values were and what I was actually doing and then that that exhaustion caught up to me and I had to leave the company and I took five months off. Jennifer Moss is a workplace happiness writer, speaker and strategist. Having moved back to Canada from Silicon Valley in 2012, she co-founded a company called Plasticity Labs with her husband. They developed happiness strategies for companies and got some big clients like Lululemon. On the cusp of signing a transformative deal in 2019, they got blindsided just days before signing, which fatally crippled morale.

1:48And in the midst of all this, it didn't escape Jennifer that she was running a happiness startup, but was desperately unhappy.

2:01Jennifer and her team discovered they could make workplaces happier, but it relied on one thing. If we reduce workload, does that improve happiness? If we focus on these traits like hope and efficacy and resilience and optimism, does mindset improve certain groups? And we found in almost every instance is that it does as long as leaders and employees are sharing the same language. So you can't just have employees focusing on hope and efficacy and resilience and optimism when leaders are just saying, do as I say, not as I do. So across the board, well-being does improve all these incredible metrics as long as people trust that the organization has their best interest at heart.

2:46They tried various approaches to grow the business. Consultancy, tech, which it turns out can't solve for happiness, Jennifer says. Data gathering, training, loads of things. But that was part of the problem. And I think that's one of the things that, you know, I regret and I would have gone back to is just really making it hyper focused on one thing. And I would have started with just the consulting to gather enough feedback to find out, okay, what would be the best problem space to resolve? Because now I look at it and I think I would have just addressed the major issues that are causing the stress.

3:24I would be focusing on fixing overwork, managing workload. And that would be the one thing I would do, that and building trust. So after you spend a lot of time in these worlds, you realize those are the things that make happiness hard to sustain because you can make everyone feel really excited about a value, really excited about gratitude for a little bit. And then you can, unfortunately, and then you can find out that it all goes back to not having autonomy, not feeling like you can choose where you work, feeling like you're working more hours than you should. I mean, there's a million different things that we could be attacking and we tried to do too much at once.

4:14There were times when the company was doing pretty well. Because we did go from startup to stay up. I mean, we had really, like I said, like pretty consistent customer base and a really high retention and our MPS scores are really high. But it just came down to feeling like we were fighting for funding all the time. Now, I think it would be easier. There's a lot more female funded programming, especially in Canada where we incubated. And there's less fear, I think, of married co-founders and just what that brings up. But I think, again, I would probably have just let one of us really lead instead of it being like we had to do it together.

4:59One of the things, too, that I think is important for early founders is to kind of not dive in both of you at one time. We have three kids. So putting that kind of financial stress on the both of us was probably a tough decision because we could have pushed it a little bit longer if we had this steady income that was kind of happening all around us. In the midst of the startup grind, something unexpected happened for this husband and wife co-founding team. We had a surprise third baby after we moved back and the startup was kind of in its full throttle state. I was, you know, we'd just come off of that kind of mindset of lean in where you have babies coming with you into the boardrooms.

5:51And it's just really difficult to juggle. And I see a lot of women now saying that they don't want to put themselves through that. And unfortunately, it's leading to a mass exodus of women in the workforce. It's why women burn out more than their male counterparts significantly. And it is this expectation to do it all, to have it all. And so I've really pushed back on this kind of lean in mindset because we all need to have micro focus. We don't do very well when we're in so many places at the same time. I also felt a responsibility, I think, to saying, yes, I wasn't at an age where now in my 40s I have a little bit, I think, more self-compassion and I'm more confident in saying no to projects and expectations.

6:45But as a woman, I felt like I had to be on every board. I had to advocate for female founders. I was constantly talking about the need for there to be more investment and advocacy for the support of married co-founders. So I felt kind of like I had to play that role because there was few of us. It's fascinating hearing about burnout from a burnout expert who burnt out. Well, for me, it led to depression. It led to anxiety. I was really anxious all the time. I felt imposter syndrome, like I'm not meeting everyone's expectations of me and I must be a fraud and that I'm running a happiness company and I'm deeply dissatisfied with life.

7:32That was something that I recognized. I recognized I wasn't spending as much time with friends. I wasn't doing the things that give me joy. I didn't feel like I had time to invest in myself and relationships were suffering. And over time, you know, at first you don't notice it. It's just this slow kind of ebbing away at you. And when you look at that timeline of burnout, great research by Dr. Marie Asberg that looks at this timeline of burnout. And it's usually 18 months to two years of just kind of slipping and then popping back up to your kind of happiness set point. And then you dip a bit again, but when you hit the wall, it's like a falling off the cliff moment.

8:19And you kind of just go, okay, I cannot do this anymore. And then it can lead to really catastrophic impacts. I think what people don't really, you know, are, what people are missing right now is that burnout is, is very serious and people, experience PTSD from it. It can impact long-term opportunities in our career. It can make it less likely that we're going to get those promotions. It means that we might not make as much money over the course of our career. So those are just the impacts that are happening in our professional lives. But our personal lives, like I said, I experienced anxiety and depression and I felt like my relationships were slipping.

9:08Those are the kind of things that we should start to recognize and pay attention to. Another part of burnout, which is something we all need to recognize too, is that we start to feel cynical. We start to question, why am I here? What is the point? We have big kind of black or white statements. Like, I'm not good at my job. This is never going to change. It's always going to stay the same. We start to have language of permanence. And in the brain, when we start having these specific black and white kind of statements or narratives that are running through our brain or we're speaking them out loud, it usually means we don't feel like we have any control.

9:51And that hopelessness and that lack of control is dangerous. Okay, so this all led to Jennifer taking a five-month break from the company in 2018 to reset and recharge and align her life with her values. At first, she felt tremendous guilt, but she then came up with a new formula for making life decisions. What will I think on my deathbed? Will I regret doing this thing or not? Jennifer returned to the company, and in the next year, they came across an opportunity that they hoped would finally be the inflection point that nearly 10 years of hard work had been building towards. The final year was really tricky.

10:33We had one company that was looking to put in a major investment, and they were going to bring us in-house. We were looking at joining a company and working with them. And they ended up being acquired around four days before the deal was going to go through. And it was a very huge investment at the time. It was, I think, half or three quarters of a million dollars that was going to be injected in to take a portion of us inside of their organization and then the opportunity to grow and then be working with this amazing group. We had worked with them as their support around building culture and happiness and measure for a while.

11:31And then this all came to happen. And the people that were managing the acquisition couldn't speak about it. So there was no way that they could give us any heads up. And that really derailed the company at that point. They struggled to raise morale again. It had been an uphill struggle for several years. So they closed the company. YMCA decided afterwards to incubate some of the work and staff, including her husband. so it lives on in some way. Jennifer now focuses more on speaking, writing and consulting. But what did she learn about business building? Until the contracts sign, until the money is in the bank, you really have to continue to just be pragmatic and you have to be careful and cautious.

12:25I think that's where a lot of my cynicism too came in and my husband, who is the co-founder, the cynicism at that point, when you think something is so rock solid, you're literally four days away and you've done all this work and there's no sign of it not being the case that you're going to get this money, you feel a little hopeless. And so that, I think, is a drag on morale. It's hard to still be getting people motivated again when things fall through. And that's, I think, another big lesson is making sure that you have backup, that you have plan B's and plan C's and plan Z's instead of putting all your eggs in one basket.

13:11I mean, that's a truism for sure in startup world. And that was the lesson that we learned is that we had hyper-focused on something that ended up not working out. I mean, it made sense for us to focus on it at the time. it seemed in all essence that it was going to happen. And it was a shock even to the people on the deal. They didn't even know that this was happening to their company in the background. So there you have one of the core challenges of being a founder in 10 minutes. Jennifer says they weren't focused enough at the beginning, but then became too focused on one opportunity at the end.

13:50You have to focus because you have a small team, but focus on the wrong thing and you're kaput. For Jennifer, although her business ostensibly failed, there were clear lessons in how to look after herself and the people she works with. I've gotten better at really spending time analyzing my priorities. So I do that daily, but I also do that over, you know, one year, five year, 10 year plan. What are my goals? And every day, am I actually doing the work that's getting me to those daily, monthly, yearly goals. And if I'm not, I have to question why I'm doing it, or I have to say no to projects that I can't participate in because it will take me away from my family.

14:32And I think it's important to note that I have a lot of privilege to be able to say that as an entrepreneur, there's a lot of stressors, but there's privilege in that you can choose, that you can make those choices. Not everyone has that choice. And so I just want to note that. But for me, because I do, I make a point to model that behavior, especially for my team. I don't work on weekends. I don't work in evenings. I make sure that I take Fridays off in the summer, and my whole team does too. I send later on my emails. I don't email people in the evenings. I don't Slack people in the evenings and I celebrate when people take time off.

15:13I post in Slack when I'm going for a walk every single day. So people feel like they can also go for a walk. And I, you know, these are simple measures, but it's really about leading by example because employees can't be what they can't see.

15:32Jennifer Moss on how to lead from the front with your mental health. So you and your team are happy and productive. Thanks for listening to this episode. I've been your host, Dan Murray-Surter. If you like this episode, please hit follow or subscribe. See you next time.