Mazarine Treyz: Hey, everybody. Welcome. This is Mazarine Treyz of Wild Woman Fundraising and today I am talking with Barbara Winter, the author of Making a Living Without a Job. This book has been an inspiration for me throughout my path through entrepreneurship. I’ve given it to other people. They have also said how incredible this book is.

Barbara Winter talks about how to keep it fresh and fun in your side gig or your business, and if you want to learn more about consulting, consider coming to the the Fundraising Career Conference in 2017.


The gig economy is now getting a lot of press from media outlets like Forbes. What do you think of places like Uber and Task Rabbit for entrepreneurs? The precarious existence of trying to work full time for these gigs and not having a steady paycheck coming in. Do you think it’s a way for people to survive long term?

Barbara Winter: Well, I think – and as anyone knows who had read my book, I’m really an advocate of multiple profit centers and having more than one income source when you build a business. So for a lot of people, things like AirBnB and Uber and Task Rabbit are just part of their bigger portfolio. I think that there certainly are a lot of people who have it as their one and only gig, and in some instances that works brilliantly. There’s so many different factors with it.

I had my first Uber ride a couple of months ago and the driver was I think pretty much a full time Uber driver and was working on her doctorate or something. So it was very interesting because I hadn’t taken Uber before and it was a bit of a drive from the Burbank Airport to where I live. So I interrogated her the entire way of course. I ended up giving her a copy of Making a Living Without a Job when we arrived at our destination.

MT:  If people haven’t read your book, Making a Living Without a Job, you advocate for people to have multiple streams of income. For example, when I started my fundraising consulting business, I taught art classes out of my car port for extra money. What streams of income have worked for people that you’ve talked with?

BW: All kinds, and your experience I think is very common, is that you have things that are kind of diverse activities. I think that’s one of the things that is really appealing to people about self employment. I’ve had so many people in seminars who would come up afterwards and say, I’ve always wanted to do more than one thing and I’ve been resisting it because I was discouraged from doing that. She said, you finally gave me permission to do that.

I think that was my experience, too. Growing up, I have a sister two years younger than I am, who knew from probably junior high age she wanted to be an archaeologist. I just watched her go right down that road and just do what she needed to do to become an archaeologist. I remember when I was in high school, about once a week at breakfast, my mother would say, ‘Well, Barbara. What are you going to be this week?’

I’d have a different answer because I knew there were lots of really interesting things to do. I remember when I went to enroll in college. I was excited. I thought, I have no idea what I want to do when I get out of college. I’m not really sure why I’m here. I’m going to hang out for four years and I’ll be an adult then. Then I will know what I’m supposed to do. When I went to enroll, they asked me what my major was going to be. I had no idea.

They said, well, you can’t enroll if you don’t declare a major. So I said English, because I thought that would be a really nice way to spend the next several years, sitting around reading English literature and having intellectual discussions with people. At the same time, it wasn’t like I think this is what I want to do for the rest of my life. When I ended up, I had a teaching degree. But it really took a lot more life experience until I got clear about not the job title that I wanted, but the kind of activities I wanted to spend my day with.

I remember the first time I wrote this down, and it felt like it was really a courageous thing to do. I wrote down, what do you most love to do? And I only put three things on the list. I would still have the same three things on the list. I like to teach. I like to travel and I like to read books. Of course when I wrote those three things down, I looked at the list. It’s like, who would ever pay you to do that?

Eventually, though, as I became more entrepreneurial and started to think about the possibility of creating my own business, it occurred to me I could create a business where I got paid to travel. I remember at one point, I had over a million miles on one airline. It was all going out to do the other thing I loved, which was teach. So it took a while to figure that all out. But once I did, then creating something that supported that became a lot easier.

MT: That actually leads into my next question. So for example, this is something that happens a lot, especially with fundraising consulting and with nonprofit consulting. So you said that people should re-evaluate every 90 days what’s working and what’s not working in my business. What if, let’s say, a consultant has two clients and they’re also doing speaking engagements, which are not paying, which they love. One of the clients, who they do not love. What do you suggest that they do?

BW: I think the really important thing to understand is that having a business is an evolutionary process and it changes over time. So sometimes those experiences that aren’t so pleasant also show us what we don’t want to include on a regular basis. But we make decisions differently depending on the age of our business.

So if we are just getting started, we pretty much have to say yes to every opportunity that comes along. But then as we start to develop a track record, then we can in our 90 day evaluation say, okay, it’s time to get rid of that and focus more attention on getting more of this because this is paying better and it’s also more satisfying to me. So I tell people the business you start out with isn’t the business you end up with.

MT: So true.

BW: When I was kind of rebuilding my whole life, actually, and moved to Minneapolis, I started doing speaking. Anyone who asked me, I would say yes. Most of the time, that was not a paying thing either. But I was doing it not just for visibility, but also practice. In fact, I spent a year after I got to Minneapolis as an editor. I became a volunteer, a backstage tour guide at the Guthrie Theater.

Every Saturday I would do tours. I would do tours. Partly it was because I was enchanted with the theater. But the other part of it was, I knew that if I went for a long period of time without doing any speaking, I would get rusty. So the way for me to just keep putting myself up in front of an audience and talking. It turned out to be a really wonderful fit. Plus I got free tickets to every show which made me very popular. So it was very good for my social life as well.

MT: Wow. You know, that’s really good advice, saying yes to everything in the beginning and then slowly reevaluating every 90 days. Okay, now what? What’s the next thing I want to do? It doesn’t have to be the thing you start out with is the thing you’re going to go with forever.

BW: Exactly, and sometimes you’ll be surprised. I had a huge gift. I’m aware of it. When I had probably been in Minneapolis for a year, I discovered an independent adult ed program that was probably also about a year old. I decided to send them a couple of ideas for classes, one of which was making a living without a job, which I thought was so radical that maybe 20 people would take it and then that would be it. We’d have covered it. But that wasn’t what happened.

The first time that it went in their catalog, I got a call from the director saying, you better know how to make a living without a job because we’ve got twice as many people as we’ve got room for. So I think we did two classes the first time. But the other thing that was so wonderful about this relationship was that they were so desperate for ideas for classes, they would let me try anything.

So I’d come up with an idea for a class that I would think, oh, this is going to be great. Then I’d do the class and walk out and think, that wasn’t as much fun as I thought it was going to be. Or we didn’t get a very good response. But it was just a great way to audition my ideas, and I think too often, we evaluate before we try. That’s futile. This way, you go into it with kind of an adventurous spirit, saying I don’t know what’s going to happen but let’s just see.

So out of that, eventually after a couple years of experimenting, I discovered the classes I loved to teach the most and the ones that got the best student response. Then from there it was just a launch into doing it on a national scale. So it really is starting in your own backyard and being willing to experiment and take it from there.

MT: Yeah. I have a friend who keeps relaunching her business and she does consulting for nonprofits. She says, okay, I want to launch. Now I’ll relaunch because that didn’t go the way I wanted it to. I see her relaunching and I see her struggling because I feel like she feels like she has to get it right the first time.

BW: No.

MT: So I’m really hoping that people like her who are listening can see that it’s perfectly okay to reevaluate every few months. Just what’s working and what’s not? Really give yourself permission to make little tiny bets on what will work and what won’t.

BW: Also to pay attention to things as they’re happening. Like I said, I sometimes walked out and was like, that wasn’t that much fun. But other times I would just practically float to my car because it had been such a joyful experience. We need to bring attention to our own response to things, because those things that are joyful experiences for us are really our superpowers, the things that are really going to become important parts of the business that we’re building. It’s an amazement to me because all the jobs I had before I was self employed, I always went into them with a fair amount of enthusiasm.

But then I would get bored and I realized that I really loved learning. But once I had it figured out, I wasn’t so sure I wanted to keep doing it. That’s been what’s been an amazement for me with making a living without a job is I’ve never been bored with it and I’ve never done anything as long as I’ve done it. The Buddhists have this wonderful description of right livelihood that I just love. They say, you can tell you’re doing your right livelihood when the work becomes more, not less interesting the longer you do it. This has been my total experience with making a living without a job.

MT: That is just fascinating. That’s worth repeating. You can tell you’re doing the right thing when the work becomes more, not less interesting the longer you do it.

BW: Exactly.

MT: You have said in previous interviews that we have multiple selves within ourselves. I know a lot of friends of mine and myself personally, in our twenties and thirties, we had frustrations that we could not have all of our selves present and used in a job, probably throughout your life. But have a series of jobs or a series of facets of our lives that can seem disjointed. Can you say more about what our multiple selves look like and how our entrepreneurship can serve that?

Barbara Winter Quote You can tell you’re doing the right thing when the work becomes more, not less interesting the longer you do it.

BW: Well, I think that’s a really interesting question because I think that self employment is the ultimate personal growth program where we really do develop a new level of self awareness and we start discovering things that, first of all, we didn’t know we could do. We also keep evolving as human beings along the way, which is incredibly exciting. I think that it’s certainly something that in a normal job situation, most of us have not experienced, or not to as great a degree as when we’re designing it ourselves. But some people have a really strong passion in their life and their profit centers are all kind of built around this singular passion.

Other people have very diverse interests and like to do things that seem to have no connection. I can remember when I have had long periods of time where I was writing and wasn’t interacting a lot with other people and was kind of sedentary, even though the brain was working. I would think, I should start a business painting houses. I need to do something physical. I need to use my body more. But there are people who do set up businesses like that, where they have things. They’re using their whole selves to do. I think as we go down the joyfully jobless trail, we become more willing to pay attention when something gets our attention and we think, you know? I’d probably be really good at teaching archery to kids.

Where did that come from? But we pay attention. We start paying attention and looking at these things that sometimes seem like random ideas but actually are a perfect fit in our portfolio.

MT: Wow. That really makes me happy and surprised because when I read other job advice online, it says things like, see what people are willing to pay you for and then just do that forever. I mean, for entrepreneurs. That can make things seem very dull and lifeless after a while because you’re just doing the same thing over and over again. I’m like you, Barbara. I like to do lots of different things. So that’s very fascinating that you say that. Why not just see where your feelings take you and not where your logic takes you?

BW: Exactly. I have not really known how to address this very well. But I’m feeling like I’m gearing up to really take it on, that I think for most of us who were born after the second world war, which is most of us, there is so much unlearning we have to do when we first go down this road. There’s so much we have learned that doesn’t serve us.

We have done a pretty good job of teaching people to be obedient and to follow directions. But to be creative and willing to find the adventure and live it? That has not been well publicized. So that’s all I have to say about that I guess.

self employment is the ultimate personal growth program where we really do develop a new level of self awareness and we start discovering things that, first of all, we didn’t know we could do. barbara winter quote

MT: That is fascinating. I feel this yearning, this need for people inside themselves when they’re entrepreneurs, or just human beings. They’ll be like, how can I also have this part of myself seen and acknowledged and understood? What you’re saying is you can. It doesn’t have to be with what you’re doing right now, but you can start doing a new thing and you can let the other thing fall away for a little while. That is so powerful. We don’t have to have the same job encompass all of our pieces of ourselves.

BW: Exactly. I tell people too, if you have very diverse interests, you have to separate them or you’ll confuse people. I’ve seen people who have had business cards that have everything on it from window washing to language translation to whatever. You’ve got to separate audiences for the different things that you’re offering. But it’s doable, and you can manage it. Another thing that people don’t realize if they haven’t been in business for themselves is that every business in the world – it doesn’t matter what our product or service is – goes through cycles.

We have times where we’re busier. We have times when things drop off. I wrote an article a few years ago about how everything felt like it came to a screeching halt in my business and I was acting like a whiny baby, saying what happened? Is it over? Then I came to my senses like no, it’s July. Your business always slows down in July. But it takes us a few years to see what our cycles are for the different things we’re doing. So sometimes people put together profit centers that are rather diverse, but change with the time of year.

For instance, I know this guy in Seattle whose main business is window washing. Well, you don’t wash a lot of windows in the winter time in Seattle. So he started his second profit center, which is brilliant. Putting up and taking down Christmas yard decorations for people. He’ll even rent them storage space. They have so many lights and things that they don’t have room in their garage to store it themselves. For a fee, he’ll take care of that for them. Which I think is just brilliant.

That’s kind of a short time frame, but it’s a big profit center for him. Then spring time rolls around and he starts washing windows again. I love it.

MT: That’s such a good idea. It could be anything. Something you can’t even think of yet, but think about what people need.

BW: Exactly, and I tell people, the best idea generating question I know is who has a problem I know how to solve?

MT: Who has a problem I know how to solve? Good question!

BW: Very often, the things that would be the most logical for us and the most profitable are things that are so natural to us, we don’t know they’re valuable to other people. I have a sister who is a natural born organizer. She can just walk into any space and straighten it up. One day I said to her – and this was before organizing was such a popular business. I said, you should really start a business as an organizer. I think there are a lot of small businesses that could really use you.

She never said anything. I kept bringing it up from time to time. About the third time I mentioned it, and again, she didn’t respond verbally at all. I kind of hit my head and said, I get it. She doesn’t know she has a gift. She thinks anyone can do what she does. I can’t do what she does. I bet she thinks we’re lazy. I do not see things the way she does. So that often really slows us down.

I have a guy who, years ago, came to a class of mine. I read his story in my seminars because I love it so much. He said he has spent ten years working in a job he hated and taking every career assessment test known to mankind trying to find what he should be doing with his life.

While he was looking out there for what he should be doing, he remodeled his house three times. It’s kind of hiding in plain sight. He said, I realized I really love to do projects that have a beginning, a middle, and an end. So he started a handyman service. That was probably 15, 20 years ago and he’s still going strong. He not only loves doing it, but he wrote me this wonderful letter. He said, I have never felt so appreciated as I do now from my customers. Then they pay me on top of that.

I just love it. I read it in my classes, read his letter. Even if I didn’t know this guy, if I just had this information about him, I would know he was going to be successful.

MT: Yeah, because he’s doing what he loves to do all the time.

BW: Doing what he loves to do. But he’s such a perfect example of oh, I’ve heard this so many times. Who’d pay me to do that? I have another story and I think it’s in my book, about my neighbor in Boulder who had this beautiful yard. She was always out working in her yard and it was on a corner. I would see cars slow down when they drove by to look at it because it was so beautiful. One day she was out working in the yard. I walked by. I stopped and talked to her. I said, Susan, have you ever thought about starting a gardening business?

She said, who’d ever pay me? I said, anyone who wanted their yard to look as good as yours. That really planted a seed. She took a master gardening class, more to give her confidence, I think, than anything else. Next spring started her business. Her first customers were her mother’s friends. Her mother was like, Susan started this business if you need help in the yard. She could probably do it. After a few months, she hired her first employee, husband who quit his job to work in the gardening business because it was doing so great.

MT: Wow.

BW: Who’d ever pay me to do that?

MT:  On a related note, you said sometimes the hardest part of the journey is being who we really are. You talked about finding your values in your business. Do you have any books or exercises that you’d recommend about finding your values so you don’t take the wrong kind of gigs or clients?

BW: Well, I’m not sure I know the answer to that question exactly. I think it’s a highly personal thing. I think that for me, my early days – and prior to starting my first business, I became a real self help junkie. I read a lot of self help books. I think there are also a lot of snake oil salesmen out there and sometimes I’m kind of surprised at some of the people that have big followings that I really think are not doing what they should do. Just a minute, please.

MT: Oh, yes.

BW: I think that taking care of the boss is a really important thing. Self care is something that we have to become very conscious of doing. We’re the biggest asset of our business. It doesn’t matter what our business is. Especially if you’re a one person operation, or even if you have employees working with you. So that’s very important. But I think we need to find those teachers and those books that inspire us and keep us stretching ourselves. I love to read biographies of entrepreneurs. I, in fact, was so surprised a few years ago. I came across a biography of Hershey, the candy guy.

I found it just fascinating. I knew there was a town in Pennsylvania. But I didn’t know its origins. He was really a social entrepreneur in many ways, and he really gave back from his business. I also happen to be a big fan of Richard Branson. I have no interest in having a business like Richard Branson does. But it’s about finding the philosophy and finding philosophies and giving thoughtful attention to yes, I want this to be part of my business. I want this to be how I am in the world. So it’s always stretching ourselves a little bit further. I have all sorts of books. In fact, I have an article I wrote a while back, 25 books every entrepreneur should have. One of my favorite books which is a favorite of many, many people is Steven Pressfield’s The War of Art which is about resistance, which I always thought, no, I’m not really a procrastinator. I never gave much thought to resistance until I read that book and realized that we all have part of us that is resistant. That keeps us from doing the things that we should be doing.

If I’m having a day where I’m feeling uninspired and unmotivated to take on whatever’s on the list for today, I just grab The War of Art, open it at random, read a chapter or two. That just fixes it. We need to have those kinds of things at our fingertips that we know will get us back on track. That’s what my library looks like. I have a huge number of how-to books but I also have a lot of personal growth books and a lot of personal stories about starting businesses.

MT: So if people want to buy your book, where should they buy it?

BW: They can buy it at Amazon, of course, or they also could go to my website, which is joyfullyjobless.com and they can order it from me. They’ll get it autographed.

If you would like to learn more how to be a successful consultant, please join us at the Fundraising Career Conference in 2017.

Join us for the 3rd annual Fundraising Career Conference April 17th, 19th and 21st 2017. Since 2015 over 900 people have attended this online conference, resulting in more successful job interviews, 42% salary increases, new jobs, better workplace environments, and more! This year we’re going deep, with sessions on how to build trust with your boss (and not get fired), how to be a better mentor and manager, creativity and play at work, and more! Learn more