The Resilient Entrepreneur, Edition #125
Hi there
I hope you had a great week!
Here are the topics in today's edition:
- Dry Spells Don’t Last. But Entrepreneurs Have to Outlast Them
- Hesitation Looks Like Thinking. It’s Just Avoiding a Decision
Please reach out with comments, questions, or suggestions for articles!
Talk soon,
Tom
TACTICS FOR RESILIENT ENTREPRENEURS
Dry Spells Don’t Last. But Entrepreneurs Have to Outlast Them
Wars stall pipelines. Admin loops kill momentum. Chaos hides monsters. Every entrepreneur faces dry spells — here’s how to outlast them.
Everybody likes progress and success. Nobody likes setbacks and dry spells.
But let’s come straight to the point: The road to success always leads through setbacks and dry spells. No matter what you’re involved with, there is no way around them. In this article, let’s not look at the daily frustrations, but at the longer dry spells you will have to endure over and over again in your entrepreneurial life.
Growth Stalls
When the war in Iran started at the end of February, markets reacted globally. At Yonder, the B2B SaaS company I co-founded, we’re very active in the aviation sector. Guess what, our sales pipeline in aviation stalled when the war broke out. Projects were shelved due to the high fuel price, RFPs were delayed, and trade shows were postponed.
Growth is the essential rationale for any entrepreneur. When it suddenly stalls, you are in trouble: Investors won’t talk to you anymore, your board becomes nervous, and suddenly you start questioning yourself whether you’re doing anything right.
It’s hard to motivate your team and yourself through such a scenario, yet it happens. The war in Iran wasn’t the first sales dry spell we witnessed; it was similar during COVID-19 and when the war in Ukraine started. You will have to grit your teeth and keep going.
Admin Loops
Change of scene. You’re trying to incorporate a new company or to close a financing round. Everything is ready — your first customer just committed, or your investors have pledged the money you need to close the round. So, what are you waiting for? Let’s go!
Not so fast. You forgot my most intimate enemy: Administration. You can buy a car online with your credit card or a house without seeing a notary, but you can’t incorporate a company or close a financing round within a day. Such acts are an administrative back-and-forth, as they require different confirmations and forms, and each player insists they need that other confirmation from that other party first.
Those admin loops turn for weeks, and they usually occur when you have absolutely zero time: Incorporating a company or closing a financing round are always urgent.
What can you do when you’re trapped in an admin loop? Absolutely nothing other than gritting your teeth through the back-and-forth.
It’s A Mess
Back to daily business. I’m sure you have taken over a job, a project, or any other role in your professional life where you met pure and utter chaos: Unorganized teams, buggy software, overdue projects, and budget overshoots.
Speaking for myself, whenever I take over a mess, I dive right in and try to clean it up. Yes, I might be a little overstructured, but structure has served me well to manage multiple projects without burning out.
Every time, after a few weeks or months into the role, when I think that I have finally gained the upper hand in the mess, I come across an unremarkable stone, and I decide to lift it. There is a monster underneath it. Welcome back to the mess. It will take you another few months to kill the monster before you can enjoy the benefits of your hard work.
And Suddenly…
Even after the darkest night, the morning will come.
Suddenly, traction is back. Deals are awarded, and your sales funnel expands again. You’re working on multiple opportunities simultaneously, and with that, the positive energy is back. You also found out that your competitors didn’t close any new deals in those months scarred by war — you questioned yourself in vain.
At the same time, all the required confirmations for your company incorporation or financing round arrive in the mail (yes, those are still delivered as paper originals).
To finish off a good day, your projects suddenly move forward after months of clean-up work. Everything falls into place.
Conclusion
Don’t be overconfident when the dry spell ends and the windfall starts. Entrepreneurship is a rollercoaster, and you need to be ready to switch from dry spell to windfall (and back) within the flick of a second.
Longer dry spells are part of the game, and you shouldn’t let yourself be frustrated or demotivated by them. So what can you do to cope with them?
First, I recommend keeping a broad pipeline of activities and opportunities. There is a fair chance that you can bridge a dry spell phase in activity A with the windfall in activity B, and vice versa. Multiple activities make you more resilient, and they reduce the risk of frustration because nothing moves forward.
Second, even the hardest challenges can be overcome when gritting your teeth and soldiering on. “Never give up” is more than a motto; it’s an attitude of life.
STRATEGIES FOR RESILIENT ENTREPRENEURS
Hesitation Looks Like Thinking. It’s Just Avoiding a Decision
No amount of hesitation removes the cons of a decision. At some point, you have to jump. Even without knowing all the details.
Speed is important, both in implementation and decision-making. But can you make decisions too fast?
Yes, there are situations where it pays off to think first before moving fast and breaking things.
However, the majority of decisions are taken too slowly, because people hesitate. People hesitate before deciding for two reasons: Either they are fundamentally unsure if it is a good idea to proceed with a proposed decision, or they fear they don’t yet know all the details behind a proposed decision.
Does this sound abstract? It isn’t, but a couple of real-life examples will help make the concepts more actionable.
Fear 1: You Are Fundamentally Unsure
Think of the last big decision in business or in private you had to take. How long did you contemplate before you made the decision?
A proposal for a new mandate. Shall I take it, or is this mandate too risky? A recurring problem with an employee. Shall I keep or fire him? Which customer red flags justify a termination of a contract?
It’s the same thing in private life. Shall I apply for this open leadership position in my organization, or are the requirements beyond my capabilities? Shall I undergo this preventive medical treatment? Is it time for a change of direction in my professional life?
All those questions don’t have a right or wrong answer. No amount of hesitation will relieve you from making a decision, even for grave decisions. At some point, you will have to jump, even if you’re unsure.
Fear 2: You Are Scared by the Lack of Details
Fast-forward. You have finally made that big decision, and you’re busy working out the details with your team. Here is a specific example.
As an active reserve officer in the Swiss Armed Forces, I command a battalion. Recently, I decided we needed to change how we deploy and rotate our tactical elements. We took multiple iterations with the team and our partners to work out the details. These iterations helped us eliminate weaknesses from our plan.
But interestingly enough, every time we came across an unresolved detail, people wanted to reverse the core decision to change how we deploy and rotate our tactical elements, or at least delay the change by one year. Feel the hesitation again? People don’t like unresolved details, but there is no way around making decisions with incomplete information. You can always come back to the open details later.
Conclusion
Of course, it is worth it to think through the consequences of a major decision before you make it. You have to weigh the pros and cons of each decision, and every decision comes with cons. No amount of contemplation, hesitation, or delay will dilute the cons.
After carefully weighing your options, just go for it and make a decision. Even if there are open details at the time of the decision. Because you will never know the full set of consequences of a major decision before you take it.
About Me
I’m a tech entrepreneur, active reserve officer, and father of three — writing about entrepreneurship, leadership, and crisis management from hard-won experience. No AI, no fluff, no promos. Just plain-text insights for people building and leading under pressure.
When I’m not solving problems, I find clarity in the mountains around Zermatt.
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