Building a business is tiring work. In the beginning, it's just you. There's nobody to coach, cajole, or encourage you.

But you keep going anyway. If you stick it out long enough, you may hire a few employees. With full-time staff, you have a built-in motivation to meet payroll, but at some point even having others rely on you can start feeling hollow.

In some ways, having a boss is easier; someone else sets your objectives and holds you accountable. You don't have to constantly motivate yourself to do more, because someone else is already asking.

Do You Get Motivated By Setting Goals?

As an entrepreneur, the motivation to always carry on has to come from inside you. To cope, a lot of us become compulsive goal setters. Our objectives become our guiding light and the reason we get up in the morning.

But even goals can start to become boring. Typical goals (hit $1 million in annual sales, start a third location, etc.) can sound good on paper but provide little emotional energy when nobody other than you is keeping score.

If you don't find your goals motivating anymore, you may want to consider replacing your goals with what Chris Guillebeau calls a "quest" in his new book The Happiness of Pursuit. You probably know the name Guillebeau from his other bestsellers, The $100 Startup and The Art of Non-Conformity. In his latest book, Guillebeau argues that pursuing a really big goal or "quest" is good for the soul.

Guillebeau describes a variety of quests, from the adventurous (Matt Krause's goal to walk across an entire continent) to the philanthropic (Scott Harrison's goal to bring clean water to everyone in Sub-Saharan Africa) to the downright bizarre (A.J. Jacobs' goal to read the entire Encyclopedia Britannica in one year).

I decided to interview Guillebeau about his new book and its application for an entrepreneur who feels like there must be more to life than yet another goal. Here's our exchange:

As entrepreneurs, we hear we need a vision for our business that is much greater than ourselves, e.g., Google's mission "to organize the world's information and make it universally accessible and useful." Is the vision statement the business version of a quest? If not, what are the key differences?

Chris Guillebeau: If a vision statement is specific enough, sure, it's a quest. Many vision statements are generic, though, just like generic personal goals. "I want to lose weight" is a generic personal goal. "I will lose 40 pounds and run a marathon in the next seven months" is a specific goal. So the same is true for companies: "We will introduce the world's first [x] and become a market leader with $100 million revenue," or whatever, sounds a lot better than "We will do good work and serve our customers."

Are all quests worthy? For example, you describe the story of a Dutch teenager attempting a trans-Atlantic sailing quest. Although certainly noteworthy, is it worth risking your life for a goal?

CG: We tend to judge the noteworthiness of a quest based on the outcome, not the process. But in reality, both the degree of risk and the noteworthiness are all about the process! In the case of Laura Dekker, the young woman who sailed around the world, sure, it was risky. In her judgment it was worth it. My quest to visit every country in the world was somewhat risky. But again, it was worth it and I can't imagine not making the attempt.

In business we hear about the importance of failing well--the idea that great entrepreneurs "pivot" when they see something is not working. Any worthy quest is going to hit roadblocks--how do you know when to push through a roadblock and when you should abandon the quest?

CG: I think it depends on two things: your own motivations and how far you've come. If you're no longer motivated and it's still early days, you should let go of the goal. "Never give up" can be terrible advice. But let's say you're coming to the end of a 10-year quest. Should you let it go then? I'd say that in that case you should focus on the long-term outcome. Will you regret it later if you give up now? If so, there's your answer: Don't give up.

You talk about the natural "coming down" off the high of completing a quest. Were you depressed after accomplishing your goal to visit every country in the world? What advice would you have for other goal-oriented entrepreneurs who accomplish something they dreamed about for years?

CG: "Depressed" is a clinical term, so I don't think I'd use it without talking to someone more qualified than me. But it was certainly bittersweet. I realized that "going to every country in the world" had been a big part of my identity for a long time and that I'd need to find something else. I guess I'd encourage those goal-oriented entrepreneurs to think about why they pursued those goals in the first place. What drove them? What were the underlying values? Next, I'd encourage them to find a new focus. No one wants to live in the past, or at least they shouldn't.

Are quests better if they have a worthy goal attached to them? 

CG: That's a great question. I think quests are worthy even without a direct contribution to charity or nonprofit work. You can do good things for yourself and for others--I don't view these ambitions as mutually exclusive.

A lot of entrepreneurs put off their personal quests and defer them until after they have cashed out of their business. Do you agree that a quest is better suited for someone not running a company day-to-day, or can a busy entrepreneur also pursue a quest?

CG: I'm interested in total life convergence. I'd never want to defer my business goals or my personal goals. Of course there are always tradeoffs--there was a guy in the book who ran 250 marathons in one year, for example, and a family who bicycled from Alaska to Argentina. It might be hard to tackle those particular quests while charging ahead full force as an entrepreneur. But the greater point is that you should be able to accomplish more than one thing at a time. If your business requires a lot of focus now, find a way to cultivate the value of adventure in small ways.

What other things should a busy Inc.com reader be thinking about as it relates to the happiness of pursuit?

CG: Many people I talked to described their journey as "a crazy idea I couldn't get out of my head." Not everyone else understood it, but it became something they simply had to do. If there are any busy Inc.com readers with crazy ideas, I think they should pay attention to them. Discontent can be a powerful motivator for positive change.

Published on: Sep 19, 2014