Hey, I'm Benjamin 👋
A Passionate Digital Entrepreneur 🖥️ with 14 years of experience in IT, marketing and building start-ups.
Remote Leadership While Traveling
Introduction
For the past several years, I have run my companies while traveling across different countries and time zones. Not as a digital nomad posting sunset photos -- as a founder who still needs to make payroll decisions, unblock engineering teams, and close deals, sometimes all before breakfast in a time zone eight hours away from my team. It works, but not by accident. Here is the honest version of how to lead effectively while your office is a carry-on bag.
1. Structure Is What Makes Freedom Possible
This sounds contradictory, but it is the most important lesson. The more you travel, the more structure you need. I block out fixed working hours every day, regardless of where I am. My team knows exactly when I am available, and I protect those hours ruthlessly. The rest of the day is mine. Without that structure, everything bleeds together and you end up neither working effectively nor enjoying wherever you are. I have learned this the hard way in a dozen different cities.
2. Your Tools Are Your Office
When your office fits in a backpack, your tool stack becomes critical. I rely on Slack for day-to-day communication, Linear or similar tools for project tracking, and video calls for anything that requires nuance. But here is what nobody tells you: the tool matters less than the discipline of using it consistently. I have seen teams with perfect Notion setups that never update them, and teams using basic spreadsheets that run like clockwork. Pick your tools, commit to them, and make sure your team does the same. The worst thing you can do is scatter information across five different platforms.
3. Document Everything, Assume Nothing
When you are on the road, you will occasionally be unreachable. Flights, bad Wi-Fi, time zone gaps -- it happens. The only way this works without your business stalling is if your processes are documented well enough that your team does not need you for routine decisions. Every recurring task, every standard procedure, every decision framework should exist somewhere your team can access without pinging you. This is not micromanagement; it is the opposite. It is giving your team the information they need to operate independently.
4. Hire Adults and Let Them Operate
If you need to monitor your team's every move to trust them, traveling while leading is not your problem -- your hiring is. I built my teams specifically with autonomy in mind. Every person knows their scope, their authority level, and what decisions they can make without asking me. When I am on a twelve-hour flight, the business does not pause. Features still get shipped, client emails still get answered, and problems still get solved. If you cannot say that about your team, fix that before you book your next trip.
5. Over-Communicate Your Context
Your team cannot see whether you are at a desk or on a mountain. So tell them. I share my weekly schedule, my timezone, and any days where I will have limited connectivity. Before I travel somewhere with unreliable internet, I make sure all pending decisions are resolved and my team knows who to escalate to in my absence. This level of transparency might feel excessive, but it eliminates the anxiety that kills remote teams: the 'where is the founder and why are they not responding?' anxiety.
6. Do Not Pretend You Are Not Traveling
Some founders try to hide the fact that they are on the move, as if their team will judge them for it. I have found the opposite to be true. When you are honest about your lifestyle and still deliver results, it actually builds trust and sets a culture where output matters more than optics. The deal is simple: I get the freedom to work from anywhere, and in exchange, I am accountable for results just like everyone else. That honesty has been far more effective than pretending to be chained to a desk in Germany.
