Lost deals, silent prospects, churning customers, and outages on your wife’s birthday. Suffering is part of entrepreneurship. Here’s how to keep going.
Entrepreneurship is awesome. You are your own boss, you work whenever and wherever you want, and you’re building a product you truly love.
Wait, not quite.
Even if you don’t have a boss as an entrepreneur, you live in a world full of constraints and frustrations.
A Small Selection of Frustrations
Here is a small selection of frustrations I’ve seen in my 10+ years at the helm of Yonder, a B2B SaaS company.
Let’s start with the commercial frustrations. You’ve worked hard to submit a great RFP response, you’ve demoed your product numerous times, and you negotiated hard to reach a best-and-final offer acceptable to both sides. Then you don’t hear from your prospect anymore. Until you receive a formal email stating that they regret to inform you that you weren’t chosen as their preferred supplier. After airing your initial frustration with your co-founders, you politely ask for feedback to understand why you were not selected. Silence.
Some other deals don’t even reach the stage of negotiating a best-and-final offer. At a certain point, the discussion just stalls. You’re left in the dark about the reasons, and you start to speculate. Maybe your competitors undercut your price? Maybe the prospect has other priorities? Maybe they didn’t understand the true value of your product? You will never know.
Losing a customer is always hugely frustrating, yet it happens. Sometimes, you know the reason why a customer wants to leave you: Price, unhappiness with the product, or organizational pressure to harmonize systems within the group. And sometimes, you don’t know the reason — the customer just terminates the contract and doesn’t want to share the reasons for their termination.
On certain occasions, you will even fail to land customers in a new market segment. Maybe your product is great for large organizations, but you can’t make money with it serving small organizations. Maybe you’re successful in your home geography, but you can’t bridge the cultural differences to customers on other continents.
And as if this weren’t enough already, sometimes your revenue growth slows or stalls due to factors you cannot control: Geopolitical developments, wars, or adverse foreign exchange rate developments.
And then, there are the technical frustrations. In a software-as-a-service business, there is always something to build, update, or fix.
Sometimes, customers camouflage their feature requests as bugs, terrorizing your team to speed up the closure of the bug ticket. You spend endless time explaining that their request is not a bug, and it therefore has a different fix timeline than “immediately.” Sometimes customers call you about an urgent bug, which isn’t a bug but a misconfiguration of their corporate IT systems.
And sometimes you truly fuck up on your side: Your system experiences grave performance issues or even a full outage. Or, still worse, you suffer a data loss that you need to recover immediately. These things will always happen in the worst possible moment — when you’re super busy closing a major deal, one day before Christmas, or on the 40th birthday of your wife. Frustrating to the bone.
We’re not done yet. Even if you are on top of the most pressing commercial and technical problems in your company, there is one more thing that drags every entrepreneur down: The daily administration grind. But let’s not waste time discussing administrative frustrations.
What To Do About It
Whining isn’t an entrepreneurial discipline. So stop complaining about your frustrations and start thinking about how to solve those frustrations.
1. Accept Reality
Start with accepting that we’re living in a less-than-perfect world. Living in Switzerland, I constantly remind myself I’m super lucky to live here; many people elsewhere are much worse off. So surely I can cope with some frustrations in daily entrepreneurial life, can’t I?
Accepting reality is a question of mindset. In many poor countries, you see many joyful people. In contrast, in many rich countries, people whine all day about non-problems.
2. Grab Every Opportunity
If you have a large number of opportunities in your pipeline, it matters less if some of them take a long time to close or don’t materialize at all.
Therefore, grab every opportunity to fill your pipeline. Now you might argue that focus is a good thing for entrepreneurs. Yes, focus is important. But it’s easier to suck as many opportunities as you can into your pipeline and then focus, rather than focusing too early and then getting frustrated that your pipeline is so small. Also, some opportunities might look vague and outside of your focus at first, but they might suddenly close and prove to be hidden gems. That’s why you should grab every opportunity.
3. Learn to Suffer
Frustrations are not fun. But they are part of life, irrespective if you’re an entrepreneur, an employee, or a parent. Sometimes, you’re on a roll, and everything falls into place, and sometimes, you have to sustain a dry spell.
Sustaining long dry spells is painful. But you still need to keep going. That’s why it pays to learn to suffer. Even the darkest nights turn into beautiful sunrises at some point. Even after the longest winters, spring will come again.
Where did I learn to suffer? As an active reserve officer in the Swiss Armed Forces. And because I’ve been an active reserve officer for more than 20 years, I know that I can cope with suffering over extended periods.
Conclusion
Given all the frustrations, is entrepreneurship still worth it? Absolutely! It’s still great building something out of nothing, finding untapped market needs, and creating great products to satisfy those needs.
And you know what? The grass is not greener for employees. You might not be confronted with all the entrepreneurial frustrations I described above. But there might be other frustrations as an employee.
