Dark Paths on the Entrepreneurial Journey

Very important note: The tech entrepreneurial community has been talking about depression and entrepreneurship. I’ve included links to some very personal and moving reads at the bottom of this post. The post I’ve written below is not meant to be about depression per se but about the dark spots along the entrepreneurial journey.

Into every journey comes darkness.

Judge risk and accept discomfort.

Find your beacons and keep them lit.

Recently, I was part of a panel talking with a group of students about careers and entrepreneurship. Perhaps it was the authenticity of the other panelists, but I said something a bit out of character. I love what I do and hope I have the opportunity to build something else down the road. So when I talk about the down sides of entrepreneurship, I focus on things like needing to be prepared for the personal cash crunch, the importance of buy in from your partner and family. But there are greater tolls that building a business can have.

This post lacks many details from my personal journey. Initially I justified that based on the perils of discussing shareholder interests and ongoing clinical trials. The truth is that the post reflects who I am with my family, my friends, my peer groups. I ask for help often but it isn’t necessarily the help people might expect.

Into every journey comes darkness.

While people generally focus on the downsides of failure, even success can lead down a path of darkness. When you take outside capital, you have a responsibility to provide an exit for your investors, which may also have been your goal all along. I’ve seen the challenges faced after the sale when the culture changes for the people who helped you build or the pieces of your dream are dismantled for integration. In companies where the CEO is still the owner, there can come a time when the signs are showing that the market is moving despite profitability. To continue to be successful, the company has to shift, which can be a challenge once the startup mentality is gone.

And then there are the traditional faces of failure: the funding rounds that go unfilled, the science that can’t be coerced into a product, the management team that can’t work together.

Since darkness lurks in the wings as success and failure, there is no way to completely avoid it. How do you accept and move through the darkness?

Judge risk and accept discomfort.

One of the key parts of growing a company is learning which risks to take. There are two components of risk taking: Can you identify risks? Can you get comfortable with taking risks (and their downsides)?

Your knee jerk reaction might be that of course entrepreneurs can identify and get confortable with risks! But think about the lens through which we each see risk. A scientist or engineer may perceive the balance between technical and market risk differently than an accountant or marketing person. Understanding and managing our own risk tolerance can help determine which risks are worth taking.

If you are one of those entrepreneurs who don’t see risk, ask the people close to you what they see as risks – and why. Hearing the perspective of family, of coworkers on potential outcomes can illuminate why a risk isn’t apparent. Our worst case scenario may be rosier or the things we value (and thus are at risk of losing) may simply be different. Knowing may not change our decision to take the risk but perhaps our actions can make those around us more comfortable with that decision.

If you already see some risks, identify some personal activities that are risky but not catastrophic. While you are trying them, think about your perceptions of risk going in and on the other side. Can you overcome your perception of risk by trying something new or different (rock climbing lessons if you fear falling)? How do the people around you react when you fail?

In business, you want to develop a disciplined approach to risk taking, accepting those risks that are simply uncomfortable and rejecting the ones that are ill advised. Using running as an analogy, there are normal feelings of discomfort – the tweaky knee, being out of breath when you push your pace – and signs that you should stop immediately – a pop and sensation that you were hit in the back of the leg may not be painful but could be an Achilles tear. With running and in business, this sense of discomfort vs. impending disaster requires you to pay attention to details while that may be the last thing on your mind.

Find your beacons and keep them lit.

IMG_20111223_113540-smallMy work is very important to me and I generally need little to no provocation to talk shop, which is great when it comes to my peer network. But don’t underestimate the power of diversity. I have pockets of my life that are deliberately (almost) work-free. My family and friends provide me the opportunity to be someone outside of what I do at work, which some days is an absolute necessity. I have found people whose friendship is like a great book – you can mark the page and come back later without missing anything. The part I work hard at is setting expectations that I can live up to. I won’t ever be that friend you talk to on the phone every day. But I will do everything I can to be there when you need me – as you are with me.

Into every journey comes darkness.

Judge risk and accept discomfort.

Find your beacons and keep them lit.

Blog posts and articles about depression and entrepreneurship from the technology entrepreneur community:



  1. 2013 in the Rearview | The Next Element - January 10, 2014

    […] Dark Paths on the Entrepreneurial Journey December […]

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