3 Personal Goals for 2016 as the CEO of a Remote Company

We all know that working remotely is great, so I don’t think I’ll have to keep convincing you about that.

Is it a viable option for every organization? Probably not, but it has been working well for us so far, and we’re happy to share our experience with it and continue the conversation around it.

As we’ve already discussed, there are PROs and CONs to working remotely, but I strongly believe that the benefits outweigh the drawbacks. Instead, I’d like to focus this post on what I personally find challenging as the co-founder/CEO of a remote company, and how I plan to deal with those challenges.

Let’s start with the hardest thing to do, at least for me.

Improving the way I manage my emotions


As a startup entrepreneur, I’ve been through tough emotional rollercoaster rides in the last few years. Managing my own emotions is challenging, but it has proven to be fundamental to achieving my goals and ultimately in allowing my company to grow and succeed.

As a CEO, you always have to project a positive and confident image, within the organization itself as well as towards the outside world.

But as a founder, I find it very hard to separate the personal side from the professional side when it comes to judging the performance of my business. I try to do my best to keep my emotions under control; however, there are three things that I find myself dealing with on a regular basis: fear, anger and a sense of powerlessness.

Fear is paralyzing. It sneaks into your brain and makes it harder and harder for you to focus on your objectives. Fear is not something that you can simply avoid: it’s part of your subconscious, so there’s no escaping it. But you have to overcome it and keep it under control. The physical separation from the rest of the team that comes with remote working can amplify those fears as well, causing you to feel less in control and like you’re spending too much time alone.

It’s lonely at the top, but it doesn’t have to be that lonely. I’ve found that one of the best remedies against fear is reminding myself that I am part of a strong and committed team.

In my previous company, I used to go out for dinner with my co-founders multiple times per week. That’s when we discussed our anxieties and managed and rationalized them together, as if we were in some kind of group therapy session. We also had great food and wine, which didn’t hurt either. Now I have to find a different way to manage these feelings. Though they’re far from being the ultimate solution, periodic meetups with the team, like our company retreats, and the few days that I spend working from our office in Bologna help a lot.

A consequence of fear and the stress that comes with it is anger. I get angry at someone when I feel that their actions are taken without a clear understanding of the larger picture. Or without taking into consideration the potential negative outcomes. Or when I think that they just don’t care. The way we communicate in a remote environment is prone to a lot of misunderstandings. And this can both ignite conflicts and prevent their effective resolution. Tools like Slack and Hangout are great, but the loss of all non-verbal communication and the switch to a mostly asynchronous communication pattern make it really difficult to solve these issues quickly.

What about that sense of powerlessness? I am perfectly aware that I am not 100% in control of what happens; the success of our company depends on our customers, but it also depends on our employees and their commitment. In that context, what leverage does the CEO really have? Plus there are times when you really feel excited about a new idea, but know that it will take a long time to carry out. I’ve found that when you share an office it’s easier to keep everyone, including yourself, excited about something for longer periods of time, but in a remote environment, it’s really easy to for that energy level to drop a bit.

At the end of the day, I believe that my task is to lead a group of individuals towards a common goal. Having to do this remotely means adding yet another level of complexity to something that is already hard to do.

That said, you cannot afford to be consumed by your negative emotions; it’s already too difficult to communicate your positive emotions to the rest of the team through the filter of a digital medium.

Finding a better balance between my personal and business goals


Working from wherever I want is great, of course. But is it effective?

As the CEO, shouldn’t I be able to choose to live in a place that will ultimately benefit the company? For example, when it comes to meeting people and working on deals, things really do take flight in “hubs” like New York, London, or San Francisco. Serendipity can play a huge role in any stage of a company’s lifecycle, and being able to easily meet people that can take your vision to the next level is vital. At the same time, being too far away from the team makes it harder to lead and promote your vision from within.

During the past six years, I’ve moved around to a few different places, trying to do what was best for our company. I originally moved from Bologna to San Francisco in 2010, just for a few months, and then again in 2011-2012 for about a year and a half. After that, I briefly came back to my hometown and then, by early 2013, moved to Berlin where I ended up staying for 2+ years (except for those two months spent in NYC).

I have been lucky to find a partner that is supportive and willing to move from place to place with me. Now we live in Venice where she has enrolled in the city’s university and I work from home. Living in Italy is effective when it comes to dealing with the team and our investors, but at the same time, it obviously limits my opportunities from a business development/corporate development standpoint.

It’s true that I still travel a lot and can be almost anywhere in the US with just a couple of days notice. However, there’s an undeniable geographical gap that doesn’t allow me to create and cultivate relationships that might be valuable for the business in the long term.

On the other hand, my experience has led me to some doubts about the effectiveness of being a lone founder in the US while the rest of your team lives in Europe. I don’t have a clear answer to all these questions, but one thing I know for sure is that I will have to constantly evaluate the idea of moving elsewhere.

Staying Healthy


Like boats, companies become slower to steer as they grow.

In the beginning, we were changing a lot of stuff almost on a daily basis. Now our planning horizon is longer, but the good news is that the boat is more solid and easier to keep afloat in rough waters. As CEO, your primary responsibility is to keep the boat afloat and expand, as fast and as safely as you can. The set of activities required to do so varies a lot with the current stage of the company, the market scenario, and your personal skills. That’s all there is to say about the job description.

But sometimes not having a clearly defined set of daily tasks sucks. You’re unable to rely on a specific routine to help you discriminate between the time to dedicate to yourself and to your health. In addition, not having an easy way to measure your own performance on a daily basis means that it’s sometimes too hard to feel good about what you have accomplished during the workday.

All these things in the long term become troublesome and start affecting your health, but it’s really part of your responsibilities towards the company to stay healthy and to be able to devote all your mental energies to its success.

Staying healthy requires planning, just like any other goal you set for your company.

Bonus: Enjoy the ride as well as the destination

This is a last minute addition, but I really loved this post by Hunter Walk on Medium. It summarizes in just a few words what I should aim towards for the rest of this year (at least).

My biggest goal for this year will be to be more thankful for the moment I am living in and take more pride in what I’ve done.

To pause and smile.

Every single day of this ride.

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