Did you know Moulsari Jain, the author of this piece, is moderating at TNW2020 this year? Join the Form Track at TNW2020 to explore how technology is changing how we create, experience, and share art.

I never took a proper vacation for most of my life. Even when I was traveling, usually to see family or friends, I was on. Even on the weekends, or in the evenings, I was on. Even when I went out for drinks, I was on.

One of the perils of being a one-man business is that you are your business, and there’s no one to pick up the slack if you switch off, so you’re always on, because you never know when an opportunity shows up.

The only time I switched off completely was when I went to a meditation retreat. And although my phone and email were off, I was meditating for 10 days, which is a nice break from the rest of life, but it’s definitely not a vacation.

I used to think it’s the best thing ever to do what you love and never feel like you’re working. The closer I got to choosing the projects I wanted and saying no to the boring ones, the more intensely I worked. I averaged four hours of sleep a night at one point. Because working became more and more fun. And I never wanted to stop.

And then I burnt out.

I didn’t know you could burnout doing what you love

I decided to take a sabbatical for a year, and spent part of it in London, writing, and making contacts in the art world, my next ambition, and developing a couple of personal art projects. Towards the end of the year, I freaked out about not having accomplished anything all year, so I did a speaking engagement in London, I did a public art installation in New York, Amsterdam, London, and Paris, and I created and delivered a 10-week workshop to Live with Passion – without quitting your job. I also created a kind of mastermind group with five women. I didn’t make a lot of money at all, but looking back, I didn’t exactly take a lot of time off. I was still on the whole time.

The following year, I felt ready to get back in the game, and got a call from an old client for a big project — and fun as it was to do, and glad as I was to make some money again, by the second quarter of the year, I really felt my burnout seething in my brain. A month later, I was melting down. By the summer, the depression set in. By fall, I was in therapy.

My mental wellbeing

Depression, much like many other illnesses, forces the body to slow down and take rest. I felt way too tired to do anything, really. Work aside, I could hardly socialize, or hold a real conversation. To be honest, I started measuring successful days as the ones that I got out of bed, got showered, and made myself some food. My best friend was constantly on call to help me get through the day, even when he was at work. It was exhausting, for me and everyone around me.

I felt like I was in a black hole of time and space. No sign of light, or lightness. Just cold, heavy darkness.

And my existence stuck inside it. And every strand of life in and around me being sucked away into the abyss, until it was no more than a distant memory, someone else’s dream that I once heard about.

For months, I fought hard, armed with the guilt of wasting so much time and not having anything to show for it. Eventually I realized I was just making myself even more tired. So I started to give in, and only felt guilty every second day, then every third.

And in between I started to find pockets of time to be a teenager in summer vacation again. Free to do anything and nothing all day, sleep, eat, read, watch movies, hang out with friends, soak up sunshine, do yoga when I wanted to move, look at art without an agenda, order takeout when I didn’t want to cook, and lay around a whole bunch, just daydreaming, or wondering at the huge gaping hole in my head. I stopped writing, I stopped planning, I stopped thinking about my career. I stopped wondering if I’d ever find a partner. Most of the time, I was too tired to think at all.

Finding freedom

But when I did find a bit of energy, I was just grateful to be aware of the freedom of the moment I was in. To feel like I was in a summer vacation once again.

I remember my school summer vacations as a kid. I remember having tons of holiday homework, and summer workshops and classes that my mom signed me up for. I remember playing with my cousins occasionally and reading a lot of teen fiction, but I also remember, as clear as yesterday, that constant feeling that I was supposed to be doing something else, like homework assignments or school reading and I was just slacking off, procrastinating, berating myself for not getting my work done with so I could truly relax. But I didn’t have the energy to get all that boring stuff done, so I just kept slacking off, and feeling bad about it.

I remember, so clearly, that I never really relaxed, even as a kid. And when I got older and started working, I didn’t really relax even over vacations. I always needed a goal, an assignment, something to keep me busy, or a feeling that I was doing something productive, even if it was seeing family. I always needed to be fulfilling some kind of external expectation of me. And I was always carrying around a metric tonne of pressure internally.

Over a year into therapy and depression, I had finally started to turn slacking off into my “job” — pretending it was what I was expected to do. It was the only way to hack my own mind and try not to feel guilt or pressure to perform.

Eventually the pressure re-emerged — I had just been suppressing it. One day, I wanted nothing more than to escape it, to stop feeling suffocated by it, and I started to fantasize about how I might feel if I died. And what if that happened that same day. Immediately. Imminently.

I never really considered harming my body, it wasn’t true clinical suicidal ideation. I had no gory thoughts. Just a very deep, desperate desire to find the exit.

Of course, I concluded, once I died, I would not feel anything. So I imagined the world without me in it, and wrote my own obituary.

I turned off my phone and took a four hour nap, dead to the world.

When I woke up, I felt a little bit freer. Just imagining not existing anymore made me feel a little less responsible for my role in the world, my intense self pressure to make an impact, to do the right thing, leave the world a slightly better place than before. It even felt like a bit of a relief to not be passionate about anything anymore. To not need anything that intensely. To just be free of all my own ideas about my own existence.

Therapy and time for contemplation helped me realize that this self pressure I’d been living with all my life was nothing more than anxiety. And that when I had the occasional freakout because of the build up of pressure and overwhelm, it was actually a panic attack.

Anxiety and panic were not words I associated with myself before.

And then I realized that my depression was like the breakdown of a sports car racing at super speed, and finally just unable to keep up with itself and burning out to a complete standstill.

I realized that I’d been living all my life in anxiety of all the things I still needed to get done, with no bandwidth left to acknowledge what I’d already done, and no moment left to enjoy what I was currently doing.

I realized that the reason I loved painting and drawing so much was because it was the only thing that let me get lost in the moment, and be fully present, without any anxiety about what I still had to get done. Just like meditation and high intensity exercise.

And I realized that depression was my body and mind’s way of forcing me to come back to “normal” speed. In alignment with each other.

We don’t live in a world where we can do things at normal speed anymore. Technology and media have forced everything to advance to a higher speed.

So be it. Technology didn’t buy us free time like the advertisements promised. Instead, it increased the speed of the race. And we are forced to work even harder to keep up with it. There’s no time to breathe, to reflect, to relax, to look around, to smile at a stranger, or run into a friend, or take a wrong train. There’s no time even to wait for a tram, every moment awake is filled with technology pouring images and data into our head, at a speed faster than we can process and reflect and conclude how we feel about the world and our place in it, and how we want to make our next move.

There’s no time

But before we break down from overload, I say, let’s slack off. Turn your mind into sleep mode — no, not lying down in your bed at night for a few hours, but that kind of sleep mode where the lights are still on, but dimmed, going on and off, floating somewhere between real waking life and dream space. But not really landing in either. Creating a tunnel between the two. Letting reality flow into our private mind space, and letting fantasy flow into what is really happening.

Don’t wait for virtual reality to take over this space too. We have a right to this most ephemeral space between our minds and bodies, the space where everything is real and also everything is possible. The quintessential Schrodinger’s cat that belongs to us all, anytime we wish to stroke it and hear its purr and see its cheshire grin taunting us teasingly.

The door to this private dimension of dreamy reality is only to be found in the moments of slacking off. The moments of doodling on your notepad while listening to a boring meeting or presentation (instead of texting on your phone), the moments of imagining your boss’ head has horns growing out of it as he talks to you (instead of pretending to be busy on your laptop), the moments of missing a train and standing on the platform just staring blankly as people pass by (instead of tweeting your ill fate), the moments of sitting on your couch listening to music and doing nothing else at all (instead of catching up on Instagram or playing candy crush on your phone).

In our current reality, you have to escape to a spa, board a flight, or find yourself in a rural environment to escape the constant demands of technology and media, of voices demanding things of you, telling you how to talk and dress and think, telling you you’re not good enough, motivating you to be your best self, giving you lists of ways to become more mindful, more fit, more environmentally friendly, more financially successful or more productive within the limits of 24 hours.

In our current reality, even as an adult, we let the voices of unknown parents lecture us and berate us and make us feel bad for not doing enough, not being enough, of telling us how and who we should be.

In our current reality, there is no summer vacation of freedom. Even if we are on holiday, we have to Instagram, blog, do yoga, eat clean, and meditate. That’s a lot of holiday homework, if you ask me.

And I want to take back my summer vacations. No holiday homework. Only slacking. Down the rabbit hole we go, no drugs involved, just a lot of time that is unaccounted for. No pressure. No parents. No bullies.

Just freedom. After all, that space between my mind and my reality is not for sale, nor for rent. Its mine and I will not let anyone plant their flag in it.

As I write this, I am sitting on my couch, I haven’t showered, I’ve got an unfinished bowl of muesli next to me, and it’s 5pm on the second day of the year.

But I finally started writing again, after many months of creative drought. And it was spontaneous. Not planned. Just a natural flow like breathing or urinating, doing it like a human does, creating something out of nothing, it goes into my body and it comes out transformed. Reality should never be the same after I have had a chance to contemplate it and shape it with my dreams. The only way I can leave any mark that I was here is by letting my dreams spill out of me, and that means taking the time to slack off, and dream. To let reality soak into me the dissolve into my dreams and come out transformed by my fantasy. Twirling together like strawberry and vanilla softies in a unicorn cone.

I say, slacking off should be the next high productivity tool. The world might be better for it.

But first, I think it’s time for a nap.

Avoid the culture shock: 5-step plan to transition from employee to entrepreneur

Ask any entrepreneur and they’ll tell you that the first step to success is to start. Yet, so many people still feel trapped in life’s rat race, dreaming of a life where they are in charge. But if so many dream of it, why do so few actually take the leap?

Because it’s a massive shock. I took the leap and ditched my 9-to-5 for the entrepreneurial 24/7. It was far from being easy, but it’s the best decision I ever made — and if you’re contemplating it, I encourage you to go for it.

Here are 2 years condensed into 5 minutes through 5 key lessons I learned transitioning from employee #50,000 at a corporate tech to leading my own tech startup. Hopefully, it’ll help you jumpstart your own journey.

1. The blank canvas: no resources or structure

It’s day 1 of your startup journey and there’s no onboarding plan, no fancy welcome package like the ones you see on your LinkedIn feed. It’s just you and your bold vision to impact the world. You’ll only ever be at this stage once, so use this blank canvas as an opportunity to design the world your way.

Startups lack the luxury of resources. Yet, small budgets and scarce time are a blessing in disguise because they cultivate out-of-the-box thinking. Not being able to afford the fancy painting set at the crafts store forced me to think creatively about my 50 cent paintbrush. In fact, my canvas may not even need that paintbrush. Maybe I can make do with nail polish. Thinking without constraints opens up a whole new world of possibilities.

While creative thinking can make up for a lack of resources, structure is crucial. To help manage my time, I use the Eisenhower matrix , consolidate data as much as possible (don’t make siloed data a challenge tomorrow!), and use smart tooling to work efficiently and create structure.

2. The importance of goodwill

Where corporations need no introduction, startups must carefully build their reputation. That starts with curating awesome experiences. Now of course there’s a myriad of ways to do this, but they don’t all have to be ‘high tech.’

My team and I actually handwrite a thank you note to everyone we work with. There are no big or small fish: every customer is equally valuable.

We’ve also set it up so users can request new features through a feedback page. Listen, learn, and act. Turning users into fans, then ambassadors proved to be a great way of building a strong community and creating goodwill .

3. I surround myself with people I can learn from

Entrepreneurship can be a lonely route, but it doesn’t have to be. There are a wealth of people in the startup world willing to share their knowledge and network. I needed only ask — and I wish I had known that sooner.

I now have 12 mentors and advisors, and engage in regular knowledge-sharing sessions with fellow startups. I’m not afraid to ask for help or reach out for advice. Surrounding myself with people I can learn from is crucial because we can’t do it all by ourselves.

4. Instead of stepping into an existing culture, I had to create my own

I’ve found it all starts with a strong company identity. A startup’s culture is built over time, and involves the personalities of the people on the team. Culture involves core values and a clear mission and vision.

Aligning my startup’s words and actions created the stepping stones of Minite. By communicating the values and mission to all of our stakeholders, I make sure everyone is on the same page.

And the great thing about startups is that each new team member or stakeholder impacts the company culture. It’s a forever fine-tuning process.

5. Corporate life is comfortable and relatively risk-free — entrepreneurship is not

Risks must be calculated and involve careful planning, though n o one could have foreseen the impact of COVID-19. Yet, this strange, unfamiliar zone we suddenly found ourselves in was also an innovation catalyst. While some businesses drowned, others pivoted.

At Minite, we went back to the drawing table. We talked to local business owners and students, two majorly impacted groups. Based on their feedback, we recognized a new opportunity and capitalized on it. We’re now going strong even during the pandemic.

Entrepreneurs need to be flexible and ready to adapt to rapidly changing circumstances. It’s easy to be trapped in tunnel vision, but letting go of (often imaginary) constraints cultivates creativity and innovation.

And that’s the great thing about startups: they’re lean. If a corporation is a cruise ship where getting everyone on board takes forever, then a startup is like your 5-year-old nephew on his shiny little bike asking you to go for a ride.

Having been a cruise ship passenger for years, I love the agility of a bike. Life to me is meant to be lived in the fast lane, where I’ll be spending the next decades racing on my shiny new bike, steering in my own direction.

My startup tripled in size in 2020: Here’s what I learned

Many founders openly talk about the challenges and triumphs that come with expanding product offerings and adding customers. But adding colleagues — especially in a remote environment — comes with its own set of growing pains and valuable lessons.

I experienced that first-hand last year when my team tripled in size. It wasn’t easy, but I learned great lessons that made me a better entrepreneur. So let me share what I discovered while scaling our team at a rate that none of us had anticipated.

First up: Context

When my team closed our $15 million Series A funding round last August, I wouldn’t have guessed that just six months later we would follow up with our $38 million Series B round.

However, as a provider of enterprise-grade cloud components that enables software teams to add in-app chat and activity feeds to their products, maybe it shouldn’t have come as a surprise. Our rapid growth came as chat emerged as the dominant medium for day-to-day communications in our new virtual reality.

So to sum up our growth: in 2020, we saw a 517% increase in revenue from our chat API product, while more than doubling our user base to support more than a billion end users.

Our team size tripled from 31 to 93 employees, and the headcount continues to increase almost daily. Today, we employ 116 people across our offices in Boulder, Colo., Amsterdam, and remotely worldwide.

A lot of people and a lot of challenges, here’s what I learned from it.

Take one step back, two steps forward

One of the most pressing issues we faced as a team while expanding was a customer onboarding bottleneck. We prioritize supporting our customers with quick response times and thorough solutions, and this became increasingly difficult to maintain while simultaneously ramping up hiring.

As Stream’s customer base grew, I found it presented a catch-22: there was a need to focus energy on onboarding new customers and ensuring customer satisfaction, but we needed the personnel resources to do so.

Then to keep up with customer demand, our new team members had to hit the ground sprinting. While that might be an easy default when things are hectic, it wasn’t setting employees up for success.

That’s why my team and I took a step back to assess our processes, and ultimately, we temporarily shifted our focus to ensure we were properly hiring and training new employees. Of course, doing so required resources from existing team members, and as a result, some core competencies and initiatives had to be paused.

For many founders and leaders, this might feel like a hard pill to swallow during a high-growth period, but I think it can definitely be worth it. It’s a short-term decline in speed that will allow you to pick up ten-fold in the long run.

Support existing employees

As the team grows, existing employees will naturally develop in their roles. Particularly, employees who were previously one-person departments may start managing teams for the first time.

This was especially true for us because we often intentionally hire people who might be one level below the title, and we encourage them to grow at Stream. Snowflake CEO Frank Slootman writes about this concept in his book Tape Sucks , if you want to dive deeper into it .

While there is ample value in this hiring approach, I soon realized I needed to make sure new managers had the proper resources and felt supported in their accelerated growth.

Over time, I became better at coaching managers to clearly communicate goals and check in regularly with their direct reports. I think it’s also smart to look for the tools that can help you at this point. For me, Lattice was the right to help us streamline this process and create organized accountability.

I also discovered that as a founder of an early-stage startup, you’re directly leading people who do the work and execute. As the team expands, that leadership role evolves and becomes more indirect.

So in order for your startup to successfully scale, it’s imperative that you and early employees trust incoming leadership hires to run their respective departments. This process can be hard because founders especially are used to having a hand in everything, but it’s necessary to relinquish some control and let others make decisions.

Evolve the culture

Lastly, the culture will evolve whether you want it to or not, and it’s essential to take an active role in shaping it.

In the early days of a startup with a small team, you naturally develop close relationships with your co-workers as you’re working long hours in close proximity. As that team doubles, triples, and even quadruples, the dynamic will inevitably shift. This is where it’s key to step in with intention.

Initially, my co-founder Tommaso Barbugli and I leaned on HR for help, focusing on the obvious things like benefits, perks, and fun team-building events. However, as the dust settled, we realized we needed to think bigger in terms of the culture we wanted to cultivate.

We agreed that it’s important to us to make Stream a place where people can learn the skills they might need to pursue their own projects or startups in the future, as I believe employees feel most content when they are progressing and acquiring new abilities.

To accomplish this, we’re starting to develop open resources such as dedicated Slack channels for learning about startups and certain coding languages, weekly technical training opportunities for employees outside the engineering department, and more.

The lesson here is that during this liminal (and hectic) period, there’s actually ample opportunity to thoughtfully mold your company culture. A happy, healthy team is the best investment you can make as a founder to sustain your business for the long term.

Scale with intention

Ultimately, the resounding lesson in scaling our organization can be best summarized as pause, assess, and move forward with intention.

I know it can be tempting to continue at full speed when the momentum of growth really sets in, but a purposeful slowdown to address necessary issues can go a long way in achieving organizational goals.

Moving quickly is a non-negotiable in the startup world, but that doesn’t mean you can’t also move purposefully.