Out-of-office replies feel harmless. But chain enough of them together and you’ve just killed a deal, a project, or your own career.

Life is unfair sometimes: It often feels like David vs. Goliath. You’re doing whatever you can against an almighty opponent. And the almighty opponents keep the upper hand, even though they are lazy.

As an entrepreneur, Goliath is not always your competitor commanding a large market share. Goliath often hides in time constraints: Stuff takes much longer than you want it to take. Since I co-founded Yonder, a B2B SaaS company, nothing ever moved quickly, and I don’t think it was our fault: RFPs were delayed, scheduled meetings were canceled at the last minute, or “priorities have shifted”.

It’s similar in my life as an active reserve officer in the Swiss Armed Forces. As a battalion commander, I don’t interact just with other active reserve soldiers in my battalion, but also with the military administration. The military administration is the Goliath of any army. In contrast to tactical formations in a 24/7 mission, they live an office-hours life. As a consequence, nothing ever moves quickly when you have to involve the military administration.

Why is the frustration that everything takes so long common to both my roles as an entrepreneur and an active reserve officer?

The Common Root Cause

The root cause of most delays is that people are out of the office all the time: Seminars, training, conferences, vacation, unpaid leave, illness, and long-term medical absences.

In many large organizations — including most of our customers and also the military administration — people don’t read their emails during their absences, not even if those absences are business-related. They just activate an out-of-office reply in their Outlook before they leave. And before they activate the out-of-office reply on Friday afternoon, they fire off a ton of emails. And then they close the laptop and leave everything behind.

Sometimes, they don’t even include an email address to contact in case of urgent issues. Sometimes, they include the contact details of their deputy, whom you can contact during their absence. And in many cases, when writing to that deputy, you get… an out-of-office reply. Because their vacations overlap, or one is on vacation and the other is attending a conference.

Do you still wonder why everything takes much longer than you want it to take?

The Contrast

Now contrast this out-of-office mentality with entrepreneurship.

When an RFP with a tight timeline is floated during your vacation, you will still have to answer it. If you only discover the unread email in your inbox after your return, the deal is dead.

When you’re experiencing an outage or data loss situation on your software platform while attending a conference, you will need to leave the plenary room, find a quiet place to dial into the war room call, and help get this sorted out as quickly as possible.

You can’t leave customer calls unanswered if they repeatedly try to reach you on your mobile phone while you’re away, even if the reason they called is unimportant.

No matter how you look at it, entrepreneurs are always on duty. It’s the same for military officers. No matter if you’re in the trenches or leading an exercise, you cannot just switch off your mobile phone and close your laptop. You’re there to make sure as many of your soldiers make it back unharmed.

What To Do About It

I’m not advocating being always-on for every petty issue. That would be a recipe for burnout. But if you want to advance things, there is only one thing you can do: Don’t let tasks lie around for too long. If you receive an email that needs clarification, reply or ask for a call immediately. Because if you reply with a delay, the recipient might be out of the office again. This is not cynical; it’s a coping strategy in a world of slow and large organizations.

Conclusion

As an entrepreneur or a military commander, you’re responsible for ensuring that your mission is accomplished, no matter what it takes. Even if it frustrates you, even if it’s unfair that those corporate employees warming their chairs have an easy life and are most probably better paid than you are.

Yes, it requires mental strength and frustration tolerance. But there is a silver lining: At some point, the leaders of large organizations will notice that those employees who are always out of the office don’t achieve anything, and they will be declared obsolete much earlier than any entrepreneur or military commander out there.