3 Reasons You Probably Shouldn’t Be Asking How to Make a Living Doing What You Love


“There are no right answers to wrong questions.”
— Ursula K. Le Guin

I’m going to go out on a limb here and say that in today’s mainstream culture, we don’t tend to value questions very much. What we really want is answers.

As such, we don’t pay much attention to whether the questions that we’re asking are the right ones.

But questions are like the destinations you put into your GPS; make the wrong query, and no matter how good a route you come up with, it’s going to take you to the wrong place.

I say this because there’s one question in particular that I see coming up over and over again with people who are unhappy in their jobs that almost always takes them in the wrong direction.

Why not to ask how to make a living doing what you love

Don’t get me wrong. There are times when this is the perfect question to ask. It’s just that it’s usually not the right question when most people ask it.

In general, there are two main questions we need to answer when we’re looking for work we love:

  1. What? As in, What do I want to be doing? and
  2. How? As in, How can I best do that?

For some reason, our minds tend to be drawn towards the second question before getting fully clear on the first. Perhaps it’s because we’re anxious to know if it’s really possible to do what we love most. Or maybe it’s because we’re tired of feeling like we’re going nowhere and want to start taking action.

Regardless of the reason, it’s a habit that misleads us. In my experience, it’s almost always better to get really clear on the what before we try to figure out the how.

Here’s why:

1. You may not want it after all.

Often my clients have ideas when they come to me about what they want to do. I had one client, for example, who was thinking of going into physical therapy. His family thought it was a great idea. While we were still exploring what he really wanted in his work, he started looking into what it would take to go back to school to become a physical therapist. The amount of school work and debt he would have to take on concerned him, and he felt a strange sense of dread and sadness as he considered it.

Fortunately, he didn’t spend much time worrying about it or trying to find ways to make it work, because as he got clearer about what he was good at, what made him come alive, and what was meaningful to him, none of it pointed towards physical therapy. It turns out that the main thing pushing him towards it had been a fear about turning 40 and not having a “suitable” way to earn a living. His inner guidance was actually pointing him in a different direction, towards equally promising and better-fitting work.

If you try to figure out the how before you’re very clear on the what, you might spend a good deal of time and worry pursuing something that you don’t actually want after all.

2. You won’t uncover what may be your best options.

There’s a reason that leading innovation and design firm IDEO suggests deferring judgment and encouraging wild ideas as their first two rules for brainstorming.

When we judge ideas or try to keep them practical, which we naturally do when figuring out how to make something work, we shut down our creativity. We discard certain ideas before they’ve even seen the light of day. And I don’t know about you, but it always feels to me like my mind can either create or it can evaluate; it has a hard time doing both at the same time.

When we’re asking the question of how, we’re in the mode of shutting down, not opening up possibilities.

Sometimes wild or seemingly impractical ideas are more doable than we realize; other times they open up a new path that leads to more pragmatic options. You can always make time in the future to get practical and ask the question of how, but if you ask it too soon, you’ll kill innovation and miss out on some of your most promising choices.

3. You can’t know what’s possible until you actually try it.

I’m all for doing research about your dream job and finding out how others are supporting themselves from it. But it’s incredibly important to remember as you do this that everyone is different. Not everyone needs the same amount of money. Not everyone will generate the same income doing the same type of work. And you can never really know what’s possible for you until you try it.

I had a client who worried he couldn’t make enough money freelancing to support his family. Another thought she couldn’t have her own business and work only 4 days a week. Still another believed she couldn’t be happy if she had to move to another state. If these three people had been more concerned with how than what, they would have turned their backs on what they felt called to do.

Fortunately, none of them did. The first made plenty of money and enjoyed the work he was doing. The second started taking Fridays off and found that her business didn’t suffer in the slightest. The third moved to Texas (not her dream destination) and found out that she was quite happy living there. All three found that more was possible than they’d realized.

How is a question we cannot truly know the answer to.

In a world as infinite, dynamic, and complex as ours, how can we possibly predict what will unfold?

We can’t. Trying to answer how keeps our minds spinning and frustrated because we can never find definitive answers for how something will happen in a world we can’t control and a future we cannot see. We can use theories to make our plans, but the route we’re going to take will always be unknown.

What we can do is tune into our incredible inner guidance and ask what action we feel called to take (or not) right now, take it one step at a time, and do that over and over again.

That’s how we discover the answers we seek. That’s how we find what we’re meant to do in the world. That’s how we determine our how.

If you’re not sure what your what is, don’t worry.

You may just need a little help. We’re taught many things in school about how to fulfill someone else’s definition of success, but we don’t learn much about how to create our own.

I offer individual and group coaching programs at various levels of investment designed to help you learn how to listen to your wisest inner self, define what success means to you, discover what you’re meant to do in the world, and get started actually doing it.

To find out more, schedule a free 1:1 call with me. We’ll illuminate your goals, clarify your challenges, and discuss what each program involves and how it can help. There’s no cost for the call and no obligation to buy anything. Click here to apply for your free call today.

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