The Unfortunate Middle

When it comes to the way we earn a living, whether entrepreneurs or employees, we tend to get stuck in the unfortunate middle…

We are taught, from a young age, to exist in the middle.

Everything in moderation. Don’t be a tall poppy, nor a shrinking violet. Good enough is good enough. The middle way, middle-class, mid-tier. That’s where we want to be. Not so big that we get cut down, and not so small that we can’t stand up. Just, you, kind of, well, average. That’s the goal.

Build a career that’s okay, not amazing, not terrible. Launch a company that’s cruising along, not struggling and not leading. Build relationships that are, well, “solid,” not empty, nor deeply passionate.

The middle—the coasting life—that’s where life is meant to be lived. That’s our aspiration.

Except that it’s not. With rare exception, the middle is not the easier, most comfortable place to be, but rather the hardest to sustain and the least rewarding on nearly every level. Sure, it protects you from the anxiety of growth and the stress of survival, but it also ends up feeling like the worst of both worlds.

This is true in nearly ever domain in life. But, if presents itself in a profound (and often massively painful) way in the world of careers, especially entrepreneurship. So, let’s use that as our example.

Let’s take starting and building a business, for example. You start with an idea. You test it and people respond. They’re digging it, and so are you. So you begin to put resources and effort into it. In the beginning, it’s just you, maybe a partner and a few people working, in no small part, out of love and for the cause.

You get to a point where things are humming along. People want what you’re doing. Maybe it’s just you and an assistant. If you have a team, it is small and tight and everyone does what’s necessary. You work hard, but nothing’s overly complicated and you’re only growing your costs when your revenue covers it. Everything is optimized, capacity is fully-utilized, you’re generating a nice bit of income, living well and contributing meaningfully to the world.

Many people can (and probably should) stay in this place. You can live an extraordinary life here, do great and meaningful work. Sure, there are always day-to-day grumbles and things you have to fix, but for the most part, life is good.

I call this phase “Simple Grace.”

For many, it’s wonderful. But, for others, at some point, we fall prey to the Relative Success Virus. We judge how successful we are, and how good our lives are in relation to those around us. And, without fail, the comparisons we make are to folks who are earning a lot more or have built something substantially larger that is affecting a lot more people. And, fulfilled as we may be, we convince ourselves we should be playing a much bigger game. We choose shallow and wide over narrow and deep. Whether we should or should not, that’s a conversation for another time. For now, let’s just say, you catch the virus and decide, “oh hell no, I’m not staying ‘small.'”

So you begin to ramp up in preparation of a push to grow.

You need more, and maybe different people. Ones who’ve got more operating experience and who will also need to get paid more. You start to hire and pay people to help you get to that next level. Your counting on them to create the bump in growth and sales needed to first cover their salaries and then exceed them. But, you’re not there yet and you may not be for some time. This adds a new level of chronic stress to your work and life. Breathe in, breathe out.

For the first time, the word “financial runway” enters the conversation.

You’ve got a certain amount of money in the bank to pay your new staff. If they don’t help you grow, they have to go and that might put not only your vision, but your entire business in jeopardy. Plus, it would just plain suck. For them, and for you. So, you work even harder than before, and push your new team fiercely because much as you want to be all chill and love everyone up, you also know, every minute of every day, you’ve got a drop dead date in your head. A Monday, Tuesday or Thursday in the not too distant future where you’re going to wake up with no more money in the bank.

Along with the new people and capacity comes the need for new and better solutions, new systems, processes, relationships and technologies. This includes management protocols, sales training, marketing strategies, financial controls, talent development, information management and training, along with manuals and policies.

On the one hand, the buildup is a necessary foundation for scalability. It sets you up for growth so that, if and when you reach that next level, you don’t utterly melt down. It becomes your new sustainable plateau, setting the table for a potential new experience of ease, but at a much higher level of operation.

Until you get to that next level, though, even if a high-level of automation happens along the way, getting all these people, products and systems developed and in place is often brutally hard, fraught with missteps, implosions and real hard costs. And, all the while, you’re racing against money and stress clock.

It puts fierce pressure on resources and amplifies complexity. You’ve got all this new capacity, but not enough new business to utilize it and, in turn, generate the money needed to pay for the people you’ve brought into the fold. Translation, massive amounts of money going out, not enough coming in yet, things constantly breaking and stifling levels of stress and sleepless nights.

This is the point so many founders end up taking outside investment. Not so much because you want to, but because you can’t breathe any more. You bounce almost violently between being pumped at the prospect and proximity of that next place and feeling like you’re drowning in stress and complexity. Visions of curling up in a ball and binge-watching Phineas and Ferb dance through your sleep-deprived, stress-addled brain. And, now more people are looking to you to take care of them. Your job is, in no uncertain terms, to not run and hide.

You’re stuck in the utterly untenable space between Simple Grace and Sustainable Complexity. It’s a glorious, catastrophic and sublimely consuming cocktail of possibility and pain.

I call this place the Unfortunate Middle.

Tech entrepreneurs often call it the dark night of the soul, which coincides with the part of Joseph Campbell’s Hero’s Journey, where you’ve committed to the grand adventure, left the ordinary world, everything becomes hard, you’re being tested fiercely and haven’t yet found the answers, allies or the way back home.

This is a place that exists purely for the purpose of forging you. It is a place that is designed to be moved through. Yet, far too often, it’s the place you end up settling into. Never doing what’s necessary to propel yourself forward into Sustainable Complexity, buoyed by structure, resources and momentum, or release yourself back into the lightness of Simple Grace.

The Unfortunate Middle becomes something of a “set-point.” You just keep reverting back to it, no matter how much pain living in this place brings with it. You dwell. And toil. And suffer. And, every day, you die a little more.

This same spectrum—Simple Grace, The Unfortunate Middle and Sustainable Complexity—isn’t just about business, it also is about every domain of life. Careers at the top have extraordinary benefits. Careers devoted to simplicity and craft bring extraordinary benefit. Those in the middle are often defined not by the best of, but by the worst of both.

Relationships that stay simple and light can add joy and fun, without the baggage of commitment and complexity. They are relationships that are about Simple Grace. Relationships that grow out of a fierce commitment to self-discovery, and building pathways and mechanisms for conversation, connection, engagement, understanding, support and joy can become astonishingly nourishing sources of meaning and life that have moved into a place of Sustainable Complexity. And, then there’s that massively fraught middle ground that tends to be marked by a whole lot of conflict and strive, the relationships that stall out in the Unfortunate Middle.

The Unfortunate Middle, in fact, defines far too much of the daily experience of far too many. Not because we want it to, but because we don’t know how to get to the other side. And, because, while it’s relatively easy to settle into a place of Simple Grace as a solitary creator, maker, lover or leader, nobody…let me repeat that…NOBODY…gets through the Unfortunate Middle alone.

You need people. To hold you. To guide you. To work with you. To collaborate and co-create with you. To, gulp, even lead you. And, that means, you also have to surrender, to be vulnerable and to welcome others into your adventure. Or else, you risk subsisting somewhat mercilessly, often for years, in crush of the Unfortunate Middle. Until either you give in, fall apart, or the thing you’ve sacrificed so much to create simply crumbles under it’s own weight. Because, as we know, this not a place to be inhabited, it is a place to be passed through.

So, my invitation, today, is this…

Ask yourself, in which of the three domains are you dwelling? In work, in your relationships, in your health, in life?

Simple Grace, Sustainable Complexity or the Unfortunate Middle?

If it’s Simple Grace, that’s fine. We all need some of that in our lives. And, if you yearn to make the leap to Sustainable Complexity, ask if you’re willing to endure the journey through the Unfortunate Middle. Are you equipped, emotionally, physically. Do you have access to the resources and people needed to make it through? And, are you willing to step into the space of vulnerability needed to receive help, if and when you open yourself up to asking for it?

If you’re in that oft sought-after place of Sustainable Complexity already, congrats. But, know too, that this is not sustainable indefinitely either. There will come a time when you are tasked with moving to the next level or contracting.

There is no sideways in business, realtionships and life, only expansion or contraction.

And, when that happens, you will re-enter a different, yet equally challenging Unfortunate Middle. Own it, expect it, prepare for it. Both on a personal level and by ensuring you’ve surrounded yourself with the right people.

If you find yourself currently operating in the Unfortunate Middle, know that this is a place that must exist, brutal as it often is, but must also be moved through. First ask if you still want what’s potentially on the other side. Knowing what you now know, you may or may not. There is no judgment either way. But, being honest about the answer is do-or-die.

If you do not, start thinking about what might need to be done to move back to a place of Simple Grace. If you do, ask yourself if you’re equipped with the resources and people, both in your venture, and outside it, that you will need to get through this gauntlet. AND, ask if you are willing to be vulnerable, own your unknowing, ask for help and then receive it. Then make assembling those who can guide and support you a priority.

Each of these phases comes without judgment, just the simple reality that they are moments along a path. How far you are willing to travel is a decision only you can make.

Question is, where are you now, and what, if anything, might you do about it?

Something to think about as we all move into a new season, filled with aspirations, plans and the desire to do more of what we’re here to do.

P.S. – To listen to this on audio, click here now.


Founders & entrepreneurs: you don’t have to do it alone! Growing a business, creating an “emergent vision” for everything from a product or service to an entire venture, then building it into something real, can be a brutally lonely process. Nobody does it alone. We all need people to guide us, to offer wisdom and advice, to hold us up, to journey along with us. That’s why I’ve created a powerful new Conscious Business Collective called The 108.

When you become one of the 108 founders invited into this new alliance, you no longer travel alone. You are a part of a fiercely committed group of visionaries, all working together to create game-changing ventures, while helping each other rise. As of March 1st, there are only about 25 spots remaining. After that, we’ll close registration until 2018 Learn more here, then get your application in now!

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