Welcome to Sabbatical — where we help ambitious people like you take a mid-career break. Sent every other week. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 28 totally chill people have signed up. That's 254 subscribers. Woo!

Considering a sabbatical? I can help.

I’m trying a fun thing: Are you considering a sabbatical? Willing to test out some of the upcoming content and resources I’m working on? Let’s chat! We can discuss:

• Learnings from 15+ interviews with people who have taken career breaks.

• Frameworks, books, and exercises to consider depending on the type of sabbatical you’re taking.

• How to best recover from burnout.

• Fun places and adventures to consider.

Totally free and no-pressure. What do you have to lose?

The Interview: Greg Portnoy

This one is for all of your startup folks. Greg spent years hustling for early-stage startups. The rewards came, but so did a feeling that he was getting away from his values. This is the story about how he got back on track.

(Read this in your browser, here)

Tell me about your sabbatical.

It was 2021, and I built the partner program at Attentive through the Series A investment round all the way to Series E. It was hyper growth in its truest form, from $20 million in revenue to hundred-plus. 

When I left there, I was hired to do a PE turnaround on a distressed SaaS startup. It was supposed to be a years-long project but it ended up being a 10 month turnaround. So, that was absolutely nuts.

From those two crazy startup experiences, I was super burned out. I didn't have a breakdown or anything like that. But I just said, “You know what? I'm done with tech, I'm done with e-commerce, I'm done with all this. I'm going to go figure something else out.” 

In December 2021, I stopped posting on LinkedIn. I left tech. I left all of that the whole the thing I've been doing for over a decade. And I didn’t come back until September 2022.

How did you approach this recharge period?

It wasn't planned. I had a nice outcome from both Attentive and from the turnaround. Nothing life changing, but I was in a very solid financial position and decided I didn't need to jump into something else. 

I went on a spiritual retreat to Sedona and did that whole thing and I was just trying to figure out what I wanted to do and reconnect with my inner self. You know, you just kinda lose track of that when you're doing startup stuff. 

With that empty space, what started to bubble up?

My number one reason to be successful is to take care of my family. My number two reason is to have a positive impact. And I felt like I had completely lost sight of number two. While I was just taking some time off I started to think about something that always bothered me: homelessness. 

So I started volunteering at a center for homeless youth downtown. I started walking on the street and talking to homeless people and learning about their stories and lives and trying to help them out. I thought, “maybe nobody has come from a private sector background and has tried to solve this problem. Let me see if I can figure out a way to help.” 

I networked with all the top executives and thought leaders around the problem nationally, and I read a bunch of books. I was really trying to come up with a private sector, tech-enabled approach to addressing homelessness. 

That sounds like incredibly hard work, how did that affect your burnout? 

I wasn't working as hard as you would work at a startup, but I was doing stuff every single day. To be honest, I really wanted it to go somewhere. I really do think it's a terrible problem, but the short version is that I realized that it was such a deeply systemic issue. 

Because of the systemic nature of the problem, the organizations created to address the symptoms of homelessness had become part of the issue and they were actually perpetuating the problem. Ultimately, I had to abandon that. It was a bit too much hubris in thinking that I could fix it. 

But it was the kind of mental break that I needed. And then I started returning to my previous industry, doing consulting and partnerships. I saw this massive gap that I'm now filling with my company, Euler. 

But as far as I knew it, if you had talked to me in the middle of that experience, I would have been like, “Yeah, I'm done with tech. I'm done with the private sector.”

What was it like having to leave behind the thing you thought would be your next move? 

I have ADHD and people with ADHD have a tendency to not finish things that they start. I also grew up with parents that kind of harped on finishing what you started. I knew that it was not going to go anywhere long before I abandoned it. 

And I'm sure you didn't want to prove people right who thought you didn't finish things.

It’s more that I didn't want to abandon an important issue. I didn't wanna feel like I was giving up on something like that, because it felt important. But I also knew in my heart of hearts that I wasn't going to be able to figure this out, at least not in any kind of reasonable amount of time.

In what ways do you feel it worked out? What are the positives to come out of that experience?

It was valuable to learn more about why this is an issue. And honestly, it was a positive to reconnect with human empathy and with those who are in a not a great position. It also was a much needed reset for my brain, I had been working at high-growth startups since 2013.

I had just been in “get shit done” mode for so long in a very specific context of privately-owned startups that I didn't know anything else at that point. All of my mental paths and grooves felt so deeply worn. This break provided a much needed reset and a kind of reality check.

When I came back to working and started a company, it actually took me a while to get back into what is now a pretty obscene level of productivity on a daily basis. I had to ramp back up to juggling a million different things and constantly switch contexts like you do as a startup founder. It took a while for my brain to get back there, but I think that I am better for it.

I think I'm able to perform better and with a clearer mind and with less professional baggage or operational baggage than I would have otherwise if I had just gone from one startup to the next. I would have just still been in those same habits.

What do you mean by “professional baggage”? 

I just had ways of working that had served me for a long time. My brain is very well suited to being entrepreneurial and I kept pushing that aside most of my life because it wasn’t valued by the companies I worked for.

When you work for someone else, they tell you what to do, when to do it, how to do it, and what not to do. It very much pigeonholed me into a particular way of thinking and working and doing. I was able to shed that and come back to working on my company Euler with a set of fresh eyes. I was able to attack it without that baggage of “This is the way I'm supposed to think or this is the way I'm supposed to work.”

A lot of ambitious people are afraid to stop because they fear they can't start again. Or that they will never be as good at their jobs as when they left. I'm curious what you would say to someone who has that exact doubt before taking a break 

I can only speak to my experience. If you're a day trader or doing something that's extremely technical, maybe coming back you’ll see that the game has changed and you don't have that same edge. I don't know about that. 

My experience has been in high growth startups and, in those companies, if you're a very ambitious person it's very easy to burn yourself out because a high-growth startup is a succubus. Anything that you have to give, it will try to suck out of you. And if you want to give, it'll suck even more. You give it an inch, it'll take a mile. For ambitious folks that are working in an environment that really wants to get the most out of their people, sometimes to a very unfair balance, it's very easy to burn out and give too much. 

But I am, by a wide margin, less stressed than I was working for other people in other people's companies than I am for myself — even though I am definitely working way harder than I ever worked before.

I think it's more about a level of motivation and passion and making sure your work aligns with your personality and your values. And you need to be very honest about this with yourself. 

For me, working for other people, especially other people that very often did not appreciate the effort that was being made, didn’t work for me. Doing it for myself and being my own boss and pushing myself harder than I've ever been pushed — but doing it in a context where I know that every incremental bit of effort will have an incremental benefit and outcome for me — is a very different kind of motivational structure.

It sounds like you said, “I need to better connect my work with my values.” One of those values led to tackling the homeless issue you cared about. And while that didn't work, you are still connecting with your values as a founder: It’s just the values are entrepreneurship and self-sufficiency. 

Absolutely. And look, in full transparency, I’ve also had some very bad luck with managers. My wife has had phenomenal managers, they were very supportive and empowering and appreciative. I have had one good one, ever, and the rest of them sucked (laughs). 

I'm not trying to self-aggrandize in any way here, but honestly it felt like I was a wild stallion that had been basically made to go race around a track. While I was good and I was successful, I was forced to do one very simple thing the way that somebody else wanted, when somebody else wanted. When I took the saddle off of myself, I became able to just open up and go exactly where I want, how fast I want, when I want. 

It's just a very, very different experience.

There had to be a period where you quit everything and then you're looking at nothing. There's nothing there. You have nothing planned, you have nothing going on. And that is a terrifying thing for an ambitious person to see because you lose a little bit of your identity. What was that like for you?

I was like a fish out of water and definitely uncomfortable. I remember when people used to ask me “Well, what are you doing? What are you working on?” And I'm like, “I'm just figuring it out.” Even though I had earned the right to just figure it out, it felt underwhelming and somewhat lazy like I was somehow taking it too easy. I grew up in an immigrant family. It was always a mindset of “If you're not working hard, if you're not grinding it out, you're not doing enough.” 

After a while I did settle into it and it was nice to not feel that overwhelming pressure and anxiety. But I did feel kind of unmoored at times.

Being a child of immigrants, were you at Thanksgiving or something, and your family's like, “Everyone here is busting their ass, Greg, and you're going to spiritual retreats in Sonoma, what the hell, man?” 

So the nice thing is that they were supportive. I had three toxic environments in a row and it just changed who I was. I was snippy, I was stressed, I was no fun to be around. And so I think that by the time I took that time off, I remember my mom saying, “that's amazing. I'm so happy.” Which for the record did still surprise me that she said that!

If you're at a bar with a friend who you respect and they ask you, “Should I do what you did? Should I just drop everything and figure it out?” What would you say to them?

Give yourself the grace to sit in your own thoughts and reconnect with yourself. Going on that spiritual retreat was so helpful. 

If you're an ambitious person, you're also very self-aware. It's very rare that we just sit in the quiet and connect with our thoughts or go on a silent retreat or a spiritual retreat. 

For ambitious people, it's very hard to get to that point where your brain is actually out of its day-to-day habits. Just take time to really disconnect and then take time to really listen to yourself on a deep level. Between all of our devices and all of our work, I don't think that we find any time to do that at all.