Below is an excerpt from my forthcoming book, In Between.

I’m bringing this forward as a result of an unexpected conversation I had with a 24-year-old first-time founder this week. While his venture failed and his circumstances are synonymous with the risk and journey of entrepreneurship, he has a bright future.

In Between lays out the approach to help entrepreneurs move between ventures. And this approach extends beyond entrepreneurs to apply to people and communities who experience profound changes in personal context, including families transitioning from the military and those departing long-term careers.

In Between didn’t start as a book. It began as an investigation into how to grieve for a failed business. I had been there twice before as an ambitious founder and in both cases, the businesses failed.

The aftermath of the first business failure was catastrophic and put me within days of personal bankruptcy. To say it was a turbulent spin-cycle of emotions is an understatement and many know this feeling.

I studied grief as a means to add a rational perspective to the emotions I was feeling. It had a limited effect because the ‘so what?’ from the literature was missing. In other words, it described how I should feel at each stage of the grieving process but provided little context-specific help.

In Between is designed to answer that ‘so what?’ of grief for entrepreneurs (and veteran families and long-term career refugees). And as many colleagues have validated in conversations on my Founder To Founder podcast, starting new chapters is an essential habit that improves with practice.

The softer landing I experienced when my second venture failed is a testament to this approach (and I wish I would have known this when it came time to leave the military).

My hope is that this book will resonate with many.

It is grounded in practical actions to navigate emotions that are taboo or misunderstood by those who haven’t lived the transition from a business, the military or a long-term career.

It will also shorten the time it takes to navigate the ‘in between’ and put you in motion to your next play.

In Between Excerpt: Chapter 6 – Sizing Up Your Next Play

Seeing yourself as part of a new opportunity is the first sign that you are in motion towards your next play.

The next step is having a framework to run a ruler over different opportunities as they appear. Remember that you are now armed with lessons and experiences that when channelled into the right opportunity will compound your rate of learning and the value you can generate.

The consequences of considering opportunities without a framework increase the risk of being oversold and investing time in organisations where you reach only a fraction of your potential.

There is a five-question framework that I use to assess opportunities. This started as a checkbox exercise. I would add these five questions in a left-hand column of a spreadsheet and then list the opportunities in a row across to the top. Each question is equally weighted and requires a simple YES or NO.

The opportunities included jobs that piqued my interest, organisations I wanted to work for (without knowing an exact role), businesses I was asked to mentor and not-for-profits I wanted to support.

As I developed a habit of using this five-question framework, I moved from spreadsheets to doing ‘the math’ in my mind each time an opportunity was presented.

This has two important benefits.

First, you become increasingly aware of the type of opportunities you want to engage in. The by-product over time is that you make quicker decisions about how to value your time and in doing so reduce the time you spend dwelling on the opportunity. Those asking you to engage also benefit by getting a quick ‘thanks, but no thanks’.

The second benefit is that you have a structured basis from which to discuss the opportunity with your partner or mentor. This increases the richness of the discussion because you’re able to dive deeper into the important factors that influence a ‘Go / No-Go’ decision.

Today, using this framework is more instinct than process.

Question 1: Does the subject excite my mind and capture my imagination?

Most people instinctively know when an idea or opportunity is captivating. They won’t often be able to articulate why. But the look on their face combined with ‘that’s cool!’ tells the story. This reaction comes before any calculation can be made about whether their skillset and experience mean they are a fit.

If this describes your reaction, answer YES to this question.

Question 2: Can I create fanatical lovers of a product or service if I were to start working on this opportunity?

This is as important for those starting a venture as it is for those building a product or business within a large business. In a startup, my measure for the number of fanatical lovers I need to create as quickly as possible is 1,000. I consider this a first major milestone. Fanatical lovers are highly likely to evangelise your product to others more effectively than your marketing efforts could hope to achieve. This drives virality that is essential to rapid growth.

The number might differ from business to business but if you are convinced that you can quickly create a large group of fanatical lovers for the problem you are solving, the answer to this question is YES.

Question 3: Can I bring my experience and expertise to the problem?

After achieving Defragmentation in Chapter 3, you are now armed with clear lessons and a narrative about your skills and capabilities. Apply them when answering this question.     

This question also has a subtle secondary meaning related to learning. By documenting lessons in Defragmentation, you are now familiar with your rate of learning. So the second part of this question is, ‘Will I have the chance to keep learning or accelerate my rate of learning?’

Answer YES if you can bring your experience and expertise to the table AND if there is an opportunity to increase your rate of learning.   

Question 4: Is there a model hiding in plain sight?

This question is asking if you can see how money is or could be made. 

For established organisations, the continuous challenge is to avoid over-romanticising how money is made and finding ways to disrupt their own business model before it’s too late.

For startups, the focus is growth. This involves experimenting with ways to make money that fuel and reinforce that growth.

For not-for-profits, the focus is growing a sustainable donor base.

Answer YES if you can see how money can be made or how this can be evolved.

Question 5: Is there room for serendipity to play out?

Call it chance, call it luck or call it faith. There is uncertainty in all facets of life and by default, there is room for happy coincidence or serendipity to play out. This question provides a guard rail for the four questions that preceded it. You can answer YES to the other four questions but you might ask this question and find that there is a very small margin for serendipity, what some might call a ‘Hail Mary’, i.e. a plan or project with a very little chance of success. This might be due to industry dynamics, an organisation in decline that lacks the ability to innovate or other environmental factors. 

If the response is more Hail Mary and less serendipity, answer NO.


One last thing…

There will be 20 pre-launch copies of In Between for those reading this post. Shoot me an email if you would like a copy. First in, first served!