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My twin brother, Jack, visited recently. It was our birthday, and we like to spend it together if we can. We turned 51 and were feeling philosophical. What had we each done, and what did we still want to do, with our one wild and precious life?

Jack raised two great kids and has a fulfilling career as a firefighter-paramedic. He also has a regret: that he did not finish college and therefore could not serve as a military officer, a family tradition.

Jack didn’t so much drop out of school as he slipped out. College was more demanding than he’d reckoned, and his restaurant job, with its good pay and great social life, was very compelling. This made him question his original goals: were college and the military really right for him? This doubt created a negative feedback loop: a weakened commitment to the goal led to less study, which led to poor grades, which led to pleasure-seeking, which led to feeling bad about himself, which intensified his doubt that he was worthy of his dream. So, he let it go.

Has this ever happened to you – you have a goal that is harder to achieve than you’d anticipated, and so you doubt that it’s right for you? It’s such a common tale, because worthy goals are almost always hard to achieve!

How do you know when to dig in – or quit?

Questions to Connect to Your Deep Desire

To answer that question, connect to your deep desire. Deep desire is the desire under the surface: what you really want when you say you want something.

If I had been a life coach back then, instead of a worried sister who just wanted her brother to be happy, I would have asked Jack these questions, which help uncover deep desire:

  • What would you do if you knew you wouldn’t fail? People sometimes downgrade their dreams to what they believe is “more realistic.” But what is “realistic” is often uninspiring – easy to abandon if things get hard – and unsatisfying if achieved. By taking the possibility of failure off the table, this question liberates people to claim their deep desire and dream big.
  • What would you do if you knew you would fail?  Goals are 99% process, 1% outcome. What process is worth doing even if you don’t get the desired outcome? This question invites you to identify what you care deeply about and what you enjoy doing for its own sake – and what you don’t. It can show you what goals you might be pursuing to please others or satisfy social expectations.
  • What feeling will this having this goal give you? One secret about goals is that we desire not so much the thing itself but the feeling we believe that having it will give us. This question can help you discern what feelings are most important to you, and if this goal is the best way to them. Following a family tradition, for example, can create a feeling of belonging, but are there other ways to feel belonging? Imagine that you’ve done it. You have the thing you want. In addition to belonging, what else do you feel? Do you like those other feelings?
  • Who do you want to be? Another secret about goals is that they are not only about the achievement. They are about who you become in the pursuit of the achievement. Completing college, for example, gets you a degree and some knowledge. More importantly, though, it shapes you into the kind of person who can get a degree – who can pursue a prescribed path, distill a great deal of information, juggle a full schedule, etc. What would you do if you knew that you are the outcome you’re striving for?

Doubt Your Doubts

The desire to complete his degree has never left my brother – endurance is often evidence of a deep desire. So, he’s picking it up again. He doesn’t need it for his career, but it’s something that he believes is worth doing even so. He wants the experience and to be someone who believes in himself and honors his deep desires.

When you can answer that way about a goal and it gets hard, you know you can doubt your doubts, not the goal.

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