Managing on the Edge – 13 Tips for Entrepreneurs

Ask any practicing entrepreneur how it is going and chances are, if you catch them in an honest moment, you will either get a really excited or really concerned and stressed answer. Such is the life of the entrepreneur, because entrepreneurship by definition happens on the edge between creation and destruction. Entrepreneurial activity thus inherently carries a lot of:

uncertainty (“I can’t be certain of how things are”)
unpredictability (“I can’t be certain of how things will be”)
emergence (“events occur without observable or understandable causality.”)

I would compare that with trying to navigate an unbeaten path through a virgin forest in heavy fog at night.

Add to this, that your understanding of where you are at and your vision of where you are trying to go can and do change as you move through the landscape (i.e. your map keeps changing and morphing as you make your path through the forest), and you are looking at a potentially stressful setting that is truly “on the edge.”

(Un)fortunately, on the journey of entrepreneurship, there is no way around that particular forest, no matter how you flip it. So here are thirteen tips that aim to help the budding and acting entrepreneur to manage this “creation on the edge”:

1. Track Progress

Tracking your progress allows you to collect evidence of your purposeful actions and progression. This is useful because you can go back to this evidence and draw reassurance from it in moments when self-doubt and insecurity have you questioning your productivity and progress. It also allows you to capture and review the path you have taken so far on your entrepreneurial journey. This is particularly interesting when you are developing different versions of your offering and venture system as you work to find the right product/market fit and pivot through business models. Tracking progress also allows you to recognise (un)productivity patterns and tackle them early.

2. Embrace the Spiral

Progress in entrepreneurship is rarely linear. So one challenge is to divorce yourself from this idea that entrepreneurial progress can be envisioned and executed in a neat five-step plan. It just isn’t that straight a line. Instead, entrepreneurship is an ongoing process where progress emerges from interchanging phases of discovery (experimentation, insights, learning) and formation (decisions, actions, venture building). Of course, one mustn’t get trapped in the loop, i.e. it is imperative that discoveries are integrated, decisions are taken, and actions are executed. But even if you do that well, you are still bound to have questions, issues, and decisions reemerge over and over on your journey. This is why the entrepreneurial process can be conceptualised as a spiral (i.e. progress does happen, but is circular). From a linear perspective, such reemerging issues could be perceived as evidence that the entrepreneur is “fighting against windmills” and not progressing. But if you embrace the spiral, you will recognise that this is natural and hence remain more likely to continue meeting challenges without losing momentum or getting discouraged.

3. Keep your eyes on your Purpose + Ethos

If you take on only one of the points listed here, it should be this one. Keeping your eyes on your purpose (i.e. what you are trying to achieve) and your ethos/values (i.e. what is driving you towards your purpose), will not only remind you why it is that you are doing what you are doing, but also what it is that you are trying to do and how you can/cannot do it. On the highest level, the purpose is your entrepreneurial vision that you are trying to turn into reality while the ethos sets out the rules of engagement as to how you can and cannot act on your journey. On the most operational level, the purpose would be the strategic relevance and contextual fit of a task (i.e. how does the completion of this task contribute towards the realisation of the vision?) while the ethos would represent the constraints that exist around the task. Either way, keeping your eyes on Purpose and Ethos will save you a lot of confusion on all levels and will allow you to stay focused and effective even in challenging times.

4. Focus on Learning
Too often the entrepreneurial journey is tackled with an attitude of achievement. While it is surely important to get things done as entrepreneur – and great to achieve success in the process – more often than not, the important breakthroughs and innovations on the journey will come from lessons extracted from the many failures one will undoubtedly experience along the way. You are therefore well advised to approach the entrepreneurial journey with an attitude of learning first. Too often have I seen entrepreneurs whose backs were broken by early failures on their path as they approached such challenges with an attitude of achievement. With such a mindset, failure takes existential proportions and can become very personal very quickly. With time, this can erode confidence completely and can leave the entrepreneur disheartened and incapable to continue. In contrast, focusing on learning allows you to embrace failure with less personal involvement and Ego, hence making it easier to deal and grow with it. In fact, I would go as far as saying that the entrepreneur’s primary duty in venturing is to learn and generate insight. The paradox here is that, once we take on this attitude, we are much more likely to achieve, as well.

5. Practice Introspection

Pretty much all wisdom traditions of this planet invite us in one form or another to get to “know thyself.” For good reason: Understanding our own mental, emotional, and spiritual structure allows us to engage much more fully, confidently, and appropriately with the world around us. Furthermore, it allows us to learn to recognise and respond to resonance; in other words, it develops our intuition and helps us discern what works for us and what doesn’t. Many introspective practices also teach us to take an observer’s vantage point on our mental and emotional processes, thus allowing us to square up with our fears, doubts, anger, expectations, etc. while not getting involved in them (i.e. practice equanimity). This can attenuate anxieties and increase our self-knowledge further still, thereby allowing us to take better, more collected and fully conscious decisions. On the entrepreneurial journey, such skills and insights are invaluable and can make the difference between a rich and rewarding journey vs a stressful, overwhelming trip through hell.

6. Ask for Help

Often entrepreneurs will aggravate their temporary miseries by isolating themselves in them. Pride, fear, ego, even shyness can all be reasons why an entrepreneur won’t reach out in moments of need. This is poor practice and serves little purpose on the journey to realising an entrepreneurial vision. Don’t be shy to approach your surrounding and ask for help, be that on the venture level or even on the personal level. The entrepreneurial journey is an inherently social affair, it would be silly at best to try and walk it completely alone. What is more, you are in the business of creating value, asking for help where truly needed in the progress is (and will often be perceived as) perfectly OK.

7. Embrace Patience

As entrepreneurs we make things happen rather than wait for them to happen. Such a proactive attitude is great and is one of the key drivers of social and economic development. However, on the entrepreneurial path we will sometimes encounter situations where, no matter how hard we try to make things happen, they will simply not progress. This can be because

A. their progression is not dependent on us
B. the time is simply not yet ripe for them to progress (think: a tree giving fruit)

In either case, trying to force the issue will only cost you energy and achieve nothing (or worse even: cause damage). Here you are well advised to embrace, practice, and cultivate patience. May not sound like an entrepreneurial practice on first encounter, but consider this: The word opportunity comes from the Latin opportunitatem and can be translated as “favourable time” …

8. In Problem Solving, focus on the “Solving” part

It seems to be instinctual for human beings to seek out causalities and understand just how exactly something came to be. This is a lovely feature of ours and has led to much insight and understanding throughout our collective history. But when it comes to problem solving, there’s a way to overdo it. There is great value in understanding a problem, no doubt. However, often we get stuck in explanations and rationalisations thereby completely losing sight of what it is that we want to achieve. In an entrepreneurial environment where resources, time, and energy are limited and need to be employed wisely, dwelling on the problem can therefore be ineffective. One way to ensure this doesn’t happen is to replace the question “Why?” with the questions “What’s the purpose?” and “What needs to happen for this purpose to be achieved?” The reason: “Why” is predominately a question about causality and focuses on exploring the past. It therefore produces mainly explanations and rationalisations. The Purpose & Achievement questions on the other hand are predominately concerned with future outcomes and thus mainly produce possibilities for progression.

9. Divorce Perfectionism

Salvador Dali said: “Have no fear of perfection – you will never reach it.” Transpose this to the metaphor of the entrepreneurial journey and it becomes evident that trying to plan the perfect trip could very well mean that you never actually embark on the journey at all. What is more, your expectations will create a lot of pressure when you do choose to walk and may limit your openness and appreciation towards possible experiences and occurrences which deviate from your idea of perfection. Do give your best and make all the efforts you can make, but liberate yourself from the mental prison that are expectations of perfection.

10. Practice Perspective

Life is bigger than entrepreneurship. And yes, your life is bigger than your venture, too. Remind yourself of this from time to time and use your introspective powers to periodically explore where your entrepreneurial journey fits into the big picture. If it seems like your venture IS the big picture, it is time to step back, take a breather, and think of a time when you weren’t working on your venture. What was in your world then? How were you in the world then? Think of how e.g. your mother sees you. Are you your venture and nothing else to her? Dwell in that perspective for a while. When all else fails, practice gratitude for your journey so far; there is no better way to open up one’s mind and heart and gain perspective than this.

11. Embrace Creative Tension and its Conflicts

I have yet to witness an entrepreneurial journey where conflict didn’t make at least a few impactful appearances. It is best compared to birthing: It takes a long time, at first it seems like nothing is happening, and when finally things do happen it gets more and more difficult until the very last moment when, in a painful finale, the act of creation is completed. This is not to say that entrepreneurship is inherently painful or follows the exact same trajectory. But where there is creative tension there will invariably be conflict that wants to be overcome. Face up to it and embrace it as a chance to develop yourself and deepen your relationships with your partners, suppliers, and customers rather than trying to avoid it and treating it as a twelve-headed daemon that has come to destroy you.

12. Practice Openness, Authenticity, Integrity

Steve Jobs valued the mirror test, i.e. checking in the mirror whether you can look yourself in the eyes and feel good about what you see. The entrepreneurial journey is full of challenges and at times you may feel seduced to take shortcuts or put your values or convictions on hold in order to get things done. My tip: Don’t do it. Stay true to yourself, act with authenticity and honesty, embrace people on your path with openness and pursue your vision with integrity. Refer to No. 10 on this list for the whys.

13. Surround yourself with people you love

Goethe said: “Treat people as if they were what they ought to be and you help them to become what they are capable of becoming.” This is precisely what you do as entrepreneur with your venture as you transform your vision to reality. But in many ways, the entrepreneurial journey is not only a journey of venture growth and transformation – you can expect to grow and transform yourself, as well. Surrounding yourself with people who genuinely love you and who you genuinely love will make it easier for you to practice what Goethe preached and work towards what you and your venture are capable of becoming even in times of difficulty.


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