Caroline Donahue and I met on a breezy (read: so sticky our clothes clung to us like peels to bananas) evening in Chicago. We were both attending BlogHer and clicked instantly. I knew I loved Caroline because she has the passion, the wisdom and the guts that I admire in people. She writes about becoming an entrepreneur, gives awesome advice/inspiration for budding creative careerists and owns Remabulous Creative Career Design. She lives in sunny LA. Lucky girl!

Our conversations are always uplifting and educational as this one in which we discuss entrepreneurship, money and doing what you’re passionate about.

People that often self-identify as Creatives also often have difficulty making a living or balancing doing what they love with paying the bills. Do you have suggestions for these types (and I suspect every one of us has some part of this in us)?

I think that people often look too much on the surface when trying to come up with ways to make money and finance a creative dream. There are stereotypes about what is possible, generally, especially in Los Angeles; every actor waits tables as one example. I think it is more important to consider very specifically what you need for the creative part of the picture financially and then to get creative about how to come up with the necessary resources. Make sure you are not taking a job that puts you somewhere you don’t want to be during peak creative time. Or take one where you have maximum flexibility. I would also advise taking a solid inventory of tasks you actually enjoy doing and try to find paid work that capitalizes on those skills.

I worked with one client who had done work that involved a lot of traveling overseas and didn’t want to be stuck in an office every day when looking to change direction. We started talking about tasks he did enjoy from his current work and one thing that came up was spreadsheets. He loves them. Could go on and on about them. This can be a huge asset when looking for other work that would want someone who has a talent for organizing complex concepts into manageable ways of charting and tracking it. Once you identify a skill and a talent and then start thinking about work that would need that kind of thinking and action, the conversation often opens up quite a bit. I think people believe that day jobs or temporary work options have to be painful, and I think that is a mistake. In fact, it is essential that you are able to see the benefit of the work for supporting your dream as well as still feel motivated to pursue it.

What do you say to the Burned Out Idealist?

In terms of the burned out, some kind of movement in a new direction is necessary. I often find myself getting burned out if I am not taking in enough new stimulation. Working from home, I can go a whole day without leaving the house as I work with clients over the phone. It is important to me to go and look at art, see shows, go out to eat with friends and so on regularly as well as travel so that I keep coming up with new ideas. I think someone who is burned out is probably feeling trapped in a routine that is not bringing in enough fresh material. I would suggest taking some kind of risk- going somewhere or calling someone or writing a letter or trying something you thought you never would. I once took a flying trapeze lesson and that jump started me for weeks and months.

After reading the Four Hour Work Week & Refuse to Choose, what practices have you personally found the most rewarding?

I think the permission to think outside of traditional and expected work and career structures was a relief from both of these books. It is a great thing to be able to think, “wow- there might be a way for me to create a structure that fits me, instead of trying to cram myself into one that everyone else has decided is right.” i definitely identify as a scanner, with many projects going and always wanting to incorporate more options into my life rather than fewer.

These two books make a really nice pair. I loved the blocking concept from Refuse to Choose- my day often runs like that, with chunks of time spent in many different aspects of my work. I prefer this as it creates a sense of movement which prevents stagnation as often. I also think the 4 hour work week is a great foundation for a scanner, as having an independent revenue cultivated can then allow for time and flexibility to pursue interests without fear of practicality. I suspect that Tim Ferriss might be a scanner himself. I think the other thing that is great about these is the specificity and practical advice given about making this kind of life work. Ferriss does not hold back at all telling how his techniques can work and how to make them work. I think often these kinds of books through a lot of vague theory around and then leave you to figure it out yourself. He certainly does not do that. And with the many different types of scanners that Sher describes and gives suggestions for, I certainly agree that these a good starting points for a creative plan.

[Note to reader: I link to the books in the column to your right, under "Now Reading."]

As a consultant/coach, what are the highs and lows of working with clients? What’s the most remarkable change you’ve seen in a client to date?

The excitement I have seen consistently is listening to a client describe a dream or project that is in some way beyond their reach and to feel immediately that it is possible. I have yet to have someone come up with something that was impossible to make work, so that is a great feeling. Usually, all that is needed is an adjustment- how long they think it will take, how many hours they can dedicate to it in comparison to the rest of their lives (often they have more time at their disposal than they thought.) and also the commitment to making it real.

I think that people can get scared of moving something from a fun daydream to a real live part of their lives. The high comes when they take that leap and see their own potential in a new way.

I think the hard part is sometimes being able to see more clearly than the client how close they are. People will do a lot of things to avoid scary change in life and it is sometimes painful to watch people distract themselves, resist continuing by putting off the next set of sessions, or by changing direction when they were about to succeed. I have helped people work through this part, which is really rewarding, but it can be hard to watch them give themselves a tremendously hard time when they don’t deserve such criticism.

Amazing changes I have seen include a client who went from an idea to a prototype that we could actually hold and look at of a product that she has long wanted to develop, a client who learned that delegating work that she didn’t enjoy doing was not only a good idea, but gave her more time and opportunity to work on the parts of her business that she does love, and in general watching people allow themselves to be themselves and to honor and respect their strengths and begin to play to them. We seem to have this idea in western society that we have to be good at everything and that it is a sign of failure if we can’t do it all ourselves. This is ridiculous and really shuts people down. I love it when a shift I help someone make- like taking Ferriss’s suggestion to get an assistant- can open people up to bigger and more rewarding, not to mention lucrative, dreams.

Remabulous?

This is a word that I made up when I was 6. i was looking at a dessert cookbook my mother had in our kitchen and it had a giant gingerbread house on the front and I couldn’t figure out a way to say it was both remarkable and fabulous. So I said it was remabulous. My family was thankfully very supportive of my dabblings in linguistics and always referred to it as my own word. I decided to use it for my business because the people I work with often do not have a pre-made job title they are looking to fill. Since they need to make up their own title, I figured my own made up word for the kind of life I hope to have would serve as inspiration.

You really want to start something. Anything. But you can’t get up the energy/tools/guts to do it. What do you do?

I’ll answer this two different ways. If you know what the something is, I would do a reverse flow chart. (I love this exercise)

1. Get a gigantic piece of paper and lay it out. If you have fun colored pens and markers, get those out as well, but a regular pen is fine.

2. At one side of the paper, preferable in a corner, draw a bubble and write it in what the end product will be. This might be “perform interpretive dance at a public venue” or “publish novel” or “have art show” or “get distribution for documentary” this is the very end of the line where you get to have a party and celebrate having achieved your dream.

3. Now, move just slightly to the left of this bubble and make smaller bubbles to indicate what must happen just before the dream. For the documentary, this might be “meet with studios” and “screen film at festivals” then move to the left and work backwards from there. “Submit film to festivals,” “research studios who have released docs on similar topics” until you get back to where you are sitting on your floor in your house with a big piece of paper.

4. Then look at what you have assigned yourself to start by doing.

5. Take a deep breath, and take one tiny step toward doing it. Make sure that this plan includes ways for you to get the tools/guts/energy you need as part of it.

I love this method because it doesn’t force you to start where the dream isn’t. You get to start where the dream is real and then see how you made it real in advance by working backwards. People are often much better at conceptualizing in this direction. what came just before is an easier thing to consider that the terrifying question of “what next” that makes you wake up sweaty at night.

If the person we are dealing with knows they want there to be something, but they don’t know what it is yet, I would suggest a pre-step to the one above. Get a small notebook- I love those little pocket Moleskines- and carry it around with you for a week. Whenever something excites you, write it down. If it’s a great sandwich, or a view, or a book you saw in a shop window or someone’s cute outfit on the bus, write it down.

Don’t bother with why you like it yet. Just a week of things that excite you. This can really get the creative juices going. I think when we are stuck we don’t even remember how to get excited. This is a way to let that happen again. Then, on the second week, start thinking about why you like the things you notice. Write that down too. Are there any connections? Does this remind you of something else? Eventually, you can start to ask yourself the question of “if I could do anything I wanted to, what would it be?” It might be related to the things you wrote down or not. Doesn’t matter. But you are more likely to find something good when you are able to see things you like around you in the world than if there is a gray dry dull feeling about life at the moment.

One of the best pieces of advice I ever received from a mentor about making a major change in my work life was: “You’ll know you are onto something when you are wanting to move towards something that feels right and exciting, rather than just trying to get away from something that feels wrong at the moment.”

I love this because it acknowledges that all work, even creative work is difficult at points, but as long as we still feel we are headed in the right direction when moving through difficulty, we can still succeed.

Thank you, Caroline! You have definitely got me revved and ready to go. We look forward to getting to know you better!
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Read previous interviews with Gwen Talks with Remarkable People for more inspiration!