Everyone Has a Year of Hell

May 11, 2020
Author: Aaron ross

Excerpted with permission of the publisher, Wiley, from From Impossible to Inevitable, Second Edition by Aaron Ross and Jason Lemkin. Copyright (c) 2019 by Pebblestorm, Inc. All rights reserved. This book is available wherever books and ebooks are sold.


Once there was a CEO who, clearly, was miserable. His business was doing $30 million and growing nicely. He was about to introduce a new product that he thought could be game-changing, and he had a strong team (according to him) that he truly enjoyed working with.

What was so bad? We don’t know exactly. But what we do know is that he was experiencing what almost all founders experience at least once on the 7- to 10-year journey: the Year of Hell.

This is never the first year. As tough as that first year is, that’s still an exploration. The potential is limitless, your long-term vision undiminished by short-term reality. You are learning, just trying to get something off the ground. You have a small, tight team. It can be incredibly stressful, full of drama, and have some near-death moments. But that struggle is . . . what it is. You make it, or you don’t, and you’re still in your hyper- creative period, figuring something new out, which is always stimulating.

No, the Year of Hell comes later (Figure 18.1). It usually comes post-traction and sometimes happens postscale, like for the CEO earlier.

It’s that one year when it’s just too darn hard on every level to keep slugging it out. You’re just under assault on too many fronts.

This isn’t a particularly profound insight, other than to say, trust me—it’s part of the journey, and you’re not doing anything wrong. Hang in there. We’ve talked with a lot of SaaS CEOs and founders, and almost all of them who’ve done it long enough have had a Year of Hell. If you’re in your Year of Hell, you’ll get through it. We’ve all been there.

Jason’s personal Year of Hell was 2008. The leads were there, the customer base was there, but we started to spend a lot of money, and it just wasn’t clicking. It was a tough year.

The strange thing isn’t that almost everyone has a Year of Hell. The strange thing is that when people get through it (if they do), most times the business does more than just improve; it Reignites and grows faster than ever.

That Reignition comes because the hell you go through forces you to retool what was stuck. You embrace it, and adapt, rather than keep doing the same old same old. David Ulevitch of OpenDNS had two different Years of Hell (lucky him). In 2010, just after returning as CEO, David had a Year of Culture Hell, because people were rudder- less after a year under a prior, professional CEO. In 2012, he had a Year of Growth Hell because the company wasn’t growing fast enough, and they had to retool the entire sales and marketing system, apply- ing many of the same ideas we’ve already covered in prior sections of this book. In both cases, OpenDNS came out of the Hell Years stronger—first with energized people, and then with predictable, scalable sales systems.

If you keep at it in your Year of Hell, you’ll see Reignition. A reacceleration of growth. It may be a full year after the Year of Hell (like at EchoSign), but it does happen often. If you have good customers, decent product, a committed team, and you keep at it with 100% dedication, unless the entire market collapses (rare in true SaaS), you’ll see Reignition, too.

Patience and dedication will see you through. Don’t give up. Do the Time and you’ll see.


During your journey, at some point you’ll plateau. It’ll probably happen more than once, in sales, personal energy, or innovation. Everyone plateaus. You feel stuck and nothing seems to kick-start growth again. If it’s a revenue plateau, it’s often because:

●  You’ve tapped out your networks and relationships.

●  You or your business doesn’t stand out; you sound like everyone else.

●  You’re overly dependent on a single person for a key function, such as bringing in leads, closing deals, or engineering.

The market or customer needs have changed, and changing the business feels impossible or impractical. You’ve hit a business model or market wall but aren’t sure what to do about it.

Sometimes a business breaks this plateau and ends up growing by hundreds of millions of dollars. And others struggle, unable to break their slump. What was the difference?

In all of these cases, comfort is the problem: not as in the “relaxed and happy” type of comfort, but the comfort found in “doing what you’ve always done”—even when you’ve done it really well or even when it hasn’t worked. Comfort as in “what is familiar, known, or taken for granted.”

Unfortunately, comfort is the enemy of growth.

The irony is, what’s already worked best for you so far (what you’re familiar and comfortable with) can be the enemy of faster growth, because you become dependent, complacent, or just too busy to keep up.

The idea of tripling your prices, redoing your product, rebuilding a sales team, firing a revenue leader, and taking six months to find some- one new, going for 10 times as many deals, creating a whole new way to generate leads, swapping out sales automation systems, writing a book in your nonexistent spare time . . . these potentially game-changing initiatives feel impossible to get to with so many other demands on your energy. A drastic change might be required to Nail a Niche or get on the path to scalable growth along with the other lessons in this book.

With any big change or investment, you’re going to obsess with how long it’ll take, how much it’ll cost and whether it’ll affect sales at all. By definition it’s a big risk with an uncertain payoff, or else you would have already done it. Honestly, most people can’t handle this much uncertainty, so staying with the devil you know is easier than “going for it.”

In a bicycle race, when your bicycle tire’s leaking air but not flat yet, it feels easier just to keep pushing. You don’t want to lose time. It’s hard for you to feel like it’s worth stopping in the middle of a race, to get off the bike, fiddle with it, and finally fix it, before starting up again.

Likewise, you put off restructuring the sales team. Or firing the executive you know needs to go. Or rebranding and repackaging. Or doubling down on a target market, making the change from “What problem do you need solved?” to “We solve X problem, do you have it?”

You put it off until you end up in a Year of Hell, with your back against the wall with no other options, and you’re forced to change.

It’s the same reason employees will bitch and moan about their manager or their job, but do nothing about it—because it’s easier (more comfortable) to stay in their job than to find a new one, confront their manager, or change their own attitude, at least in the short term.


As we went over in Part I: Nail a Niche, Aaron didn’t reach a personal Escape Velocity motivation to grow his income and business until he got married and started a family, going from zero to 10 kids in less than 10 years (which is a whole ’nother story).

Because the family grew so fast, the money needed to grow fast, too. They chose to grow the money to support their life, rather than fit their life into the money. That’s why their money grew fast—he had an epic Forcing Function he couldn’t hide from.

Those who succeed in making the big leaps find the motivationwhether through drive or passion—to sustain them through the ups and downs of Doing the Time, or a Year of Hell.

You have to want something as badly as a drowning person wants air.

Without that kind of “I need to breath” motivation—from any mixture of ambition, passion, desperation, or fear—you’re going to keep falling back into your habits, routines, and comfort zone.

What are you willing to lose a limb for? What do you want so badly that you don’t care about “how you look”—to friends, family, or employees—in order to get it?

If you can’t find something that drives you to change your own life or your own contribution at work, you’ll end up getting more of what you already have.

If you’re reading this and are thinking “it makes sense, but there’s nothing I want that badly”—dig into the next Parts, VI and VII. The ideas around Forcing Functions are the main way Aaron predictably motivates himself to do things he doesn’t want to do, but that need to get done.

This is part 2 of From Impossible To Inevitable‘s 18th chapter. Click here to read chapter 19th!

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