Being an entrepreneur has made me love outdoor life more than ever

As a founder, these are the things that keep me up at night

Kipkorir Arap Kirui
Prototypr
Published in
6 min readApr 9, 2019

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Being an entrepreneur is one of the most romanticised life choices in society. For some reason, we have managed to paint it as a rosy garden that every young person should try instead of “building other people’s dreams.” While being an entrepreneur has its upsides, I don’t think we talk enough about the challenges or downsides.

This post might sound like a case against entrepreneurship, but that is not so. It just tries to paint a more realistic picture of how it is on a day-to-day basis.

So as not to scare anyone who wants to be an entrepreneur, I will only highlight the top five things that I find myself often worrying. Additionally, I will focus on what goes on in my head as the co-founder as opposed to the challenges faced as a company.

First, Tanasuk Africa in 15 seconds

Tanasuk Africa is a design thinking and software consulting firm working with organizations across different countries building or looking to build products for African markets. We leverage the power of design thinking and agile software development to design and take digital products to market. As at the moment, the team is made up of ten people. I am the CEO of Tanasuk Africa.

Perhaps the most confusing element of the company I run is the association with iHub. We also do business as iHub Software Consulting (iSC) because of a co-branding agreement that Tanasuk Africa has with iHub. Makes sense?

I was on the Chini ya Maji podcast recently and talked at length about what we do and why we do it. Give it a listen and subscribe

Now to the exciting part of the article. While it can be rewarding being an entrepreneur there are quite several challenges and worries along the way.

1: Am I crazy for choosing this option?

I didn’t start the company straight off school so what that means is that I have the opportunity to work in a stable environment. There is nothing stable when a company is young. One minute things are going well and the next you are wondering whether you will survive or not. Case and point — we closed 2018 with a robust pipeline only for three very crucial leads we had passed critical review stages to fall between the cracks. All of a sudden the first part of 2019 did not look very promising.

Being a product designer compounds this issue. As a relatively young and lucrative field in African tech, there are so many excellent opportunities. European and American companies are also willing to relocate On LinkedIn, a good number of recruiters reach out with perfect openings.

When things are hard, it is easy to wonder if I chose the wrong option. It is easy to wonder why you seem to always go for the hardest choice.

2: Am I too hands-off?

If we have worked together, you might have noticed that I always prefer to let people find their way to the solution instead of managing every aspect of it. Most times my role is to set the goal and play the lead role during project kick-off. I then fade into the background, and this approach has served me quite well. However, there are situations it hasn’t. At times, I assume that my instructions are apparent only to be proven wrong by the outcome. Establishing clear processes has helped with this issue but once in a while things fall between the cracks, and I wonder whether I should be more hands-on. I can’t.

How will my team learn if they are not allowed to fail or try different approaches? It still doesn’t make it easy. At the moment, barring maybe one, our clients have great things to say about us. Being hands-off is putting that at risk.

3: Why won’t the client pay on time?

I would have never guessed that collections would be my biggest challenge as an entrepreneur. I would have never imagined NGOs would be the worst offenders. Dealing with the finance departments of NGOs at times is an extreme sport. Some say they didn’t see your invoice; others were on leave; others didn’t get the money on time from the donor (because they didn’t share the necessary reports on time), and so forth. It is odd seeing that many of them claim to create a positive impact in the world. I guess treating their suppliers well is not on that list. I have had better experiences with clients in the corporate sector.

4: Peer pressure

Few entrepreneurs will admit this, but it always feels like everyone around them is killing it yet as an entrepreneur you are barely making ends meet. The pressure comes both from your employed friends and fellow entrepreneurs.

With your employed friends, they have probably made significant strides at work and can afford a very different lifestyle from what you can. They probably travel a lot and go on holiday frequently. This is because they have a stable income and can reliably plan for things.

Your fellow entrepreneurs might be getting great publicity and signing significant deals. It is easy to feel that you are putting in as much effort or even more but making little headway. It is a bit ironic though because deep down you know everyone is running their race.

5: Does the team still have faith in me?

I am an optimistic person. I think it is almost impossible to be an entrepreneur and not be an optimist. In each situation, I bet on the best outcome and make promises to my team based on positive outcomes. As a result, I have broken a fair share of the promises I made to my team. With each broken promise, there is the chance that some of my team members start losing faith. Even with the transparent way we run the company, this is still something that keeps me up at night.

Bonus point: Will I ever take a proper break?

Many people think that entrepreneurs can take time off at any time. On paper, this is possible. However, in reality, as an entrepreneur, you will always have a lot of pressing issues that have an immediate impact on the viability of the company. As a result, I find myself only taking time off when I am tired to a level where I can barely do anything. The most I can get at this point is a week. Two weeks is my ultimate dream.

Coping mechanisms

As with any challenge, one has to figure out how to solve the problem or cope with it. As we work on growing our company, I have had to figure out ways to deal with the challenges I face. Some are positive while others are not.

The negative ones include spending a lot of time on social media. When I am particularly stressed I have noticed I spend more time on Twitter and Instagram than usual. Facebook has never been an issue as I deleted my account a couple of months ago.

Luckily I have more positive coping mechanisms at this point. I have had to work on this over some time, but I am glad I did.

  • Remind me that we are playing a long term game — you can not achieve success overnight. It takes time. Consistently reminding me that we are playing a long term game helps set things in perspective
  • Conversations with fellow entrepreneurs — misery loves company. Talking to other entrepreneurs reminds me that I am not the only one facing challenges and this is surprisingly reassuring
  • Taking time off — I am learning to take time off more frequently. It can just be a day where I do something different or sit at home and chill
  • Working out and hiking — this, hands down, is my best coping mechanism. I go to the gym at least three times a week and hike at least once a month. I love the physical gains, but even more importantly it keeps me calm
  • Meditation — a new addition to the list but so far so good. I used Calm for this, and I can now do 15 minutes without my mind wandering too much

Being an entrepreneur is an exciting thing to do. It is full of challenges but worthwhile if you hang in there. Even if your first, second, third, or even fourth venture doesn’t pay off, you will still have learned a lot.

Kennedy Kirui is a Nairobi-based Product Designer, UX researcher, and Sprint Master. He is the CEO and Co-founder of Tanasuk Africa (dba iHub Software Consulting) — a design thinking and software consulting firm. Kirui also co-founded Nairobi Design Community (NDC) and is a Product Strategy GDE (Google Dev Expert). You can find him on Twitter as KiruiK.

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Ex-child, Reluctant adult, Experience Designer, UX Researcher, Design Facilitator, Senior Product Manager, Co-founder Made by People, Product at Microsoft