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Episode 202: Lessons From Working Independently—with Steven Cristol

Deb Zahn: Hi. I want to welcome you to this week's episode of the Craft of Consulting Podcast. So, on this podcast, we're going to talk about working independently. So, if you're an independent consultant or you're thinking of becoming one, this is a great episode to think through the details behind that and some of the things that you need to do or some of the things that you shouldn't do to have it work for you. It's also really helpful in terms of deciding if it's a great fit for you. So, I brought on someone who actually wrote a great book about this. Steven Cristol is going to be on the show talking about sort of the do's and don'ts behind being independent and ways that you can assess whether or not it's a great choice for you, and if you pick it, how you can make it work best for you. So, let's get started.

Hi, I want to welcome to my show today, Steven Cristol. Steven, welcome to the show.

Steven Cristol: Thanks, Deb. It's really a pleasure to be here. I have a lot of respect for the resources you've offered, consultants, and people who want to be one.

Deb Zahn: That's wonderful. Well, thank you so much. Let's tell people what you do.

Steven Cristol: So, I've been doing this for a long time. So, what I do actually has evolved quite a bit over the years. When I left my last corporate job, I was originally helping companies with brand management and how to position their brands in the market, how to simplify customer experience. I did that for a number of years and realized that in just about every company, there was a big disconnect between how brands are managed and the products and services that get developed. And of course, that became a real issue because what a company says and what it delivers is often not the same thing, and that's why.

So, I developed a system for bringing brand management and product development closer together, more in alignment. I've spent a lot of the last 15 to 20 years advising companies on what products to make and not make, which is just as important and what features those products should have. The work is still evolving because it turns out that the same method that's used for prioritizing product development investments works very well for prioritizing investments in supply chain, investments particularly in sustainability when a company is trying to arbitrate between do we make our data centers more efficient or do we do compostable packaging or do we put a water recovery system in our factories. It's all about choices, which is what strategy is. And so if you ask for the simple answer of what I do, it's helping companies make better choices to create value for their customers and stakeholders.

Deb Zahn: I love that. Well, and what's interesting, so we're not going to talk about that, but it applies to the book that you wrote that is about lessons of working independently because that's all about choices too.

Steven Cristol: Yes. I mean, and actually it has evolved even further. It turned out that model has been excellent for coaching, which I also do because when people are making choices among alternatives, one of those alternatives may be staying in their current job or with their current company, but they may have two or three or four other possible paths that they've thought about, wondered about. There's a very disciplined way to arbitrate between those that still brings in all the psychological and emotional considerations in addition to the rational ones.

Deb Zahn: That's wonderful. Well, we're going to dive into some of the details of the book and we'll have a book, NO BOSS! The Real Truth about Working Independently, that has your lessons from 30 years of doing this. We're going to have a link to that in the show notes. But before I get into some of the specifics you talk about, if you had to take a step back and you think when you look at working independently, what are your top two sort of biggest, "This definitely is a thing to do and this is definitely a thing not to do"? Are there any that would jump out at you?

Steven Cristol: Well, I think the biggest thing to do is to know yourself well enough to know if you're a good fit for independent work and to know your motives because some people leave their jobs for all sorts of reasons, right? Sometimes it's to just escape a horrible boss. But a lot of times it's because they're feeling undervalued or maybe they have a great idea for doing something new that can't be done inside of their company environment. Or maybe they just want to succeed or fail on their own and see what that feels like. There's a million possible reasons, right?

And so make sure of your motives. Before you take the plunge, there are some important questions. I think I put 30 of them in the book on that you should ask yourself to really get in touch with the truth about his independent work for you because it is so easy to underestimate the benefits of working for a great company, being highly valued, having colleagues that you love to see every day, and having people to bounce ideas off of. Lots of reasons to do that. I ultimately had to decide after spending 10 years in five companies that maybe it was time for me to do something that wouldn't have to be coloring between the lines quite so much, or inside the lines, I should say.

Deb Zahn: Wonderful. And you mentioned, and I'm going to skip ahead, sort of the know thyself, which of course I love that you quoted the Temple of Apollo in Delphi because I know all three of them, all the three of the maxims, and I love them all.

Steven Cristol: Oh, you do?

Deb Zahn: Do you know all three?

Steven Cristol: I know. Well, I talked about know thyself and nothing to excess, but I don't remember the third one

Deb Zahn: When I learned the third one, I loved it, which is, certainty brings ruin. And I thought, "What a powerful path," because you know you can get tripped up by being absolutely locked into the certainty of things. So, the third one is actually one of my favorite ones.

Steven Cristol: Thanks for reminding me. Don't tell my high school Latin teacher that I forgot that.

Deb Zahn: That's OK. But I was delighted that you have that in there. And again, I know one of the things that I loved about the book is that you do have a series of questions, not just, "Hey, do you think you'd like being independent?" but really delve in deeply into some of the questions associated with knowing yourself and knowing what independent work might look like for you. What are some of the other things that you would have people consider when they're looking at themselves in the mirror and saying, "Is this the right choice for me?"

Steven Cristol: Well, the first thing they have to commit to is brutal honesty because really understanding your strengths and weaknesses are critical and you'll learn a lot more about those on your own. But in the meantime, you have to just decide, "What am I really good at? What am I not so good at? What will I never be good at? What can I be good at that I may not be as good as I need to be now?" Because it's always continuous learning and there's always possibilities. I think you have to really look back over your life and think about persistence and how well you've stood up under difficult times. I think you need to be willing to ask for help from others, which a lot of people go out on their own and feel like they have to be an island. That's a trap. I think you have to think about the times in your life that you've gone outside your comfort zone and how that worked out.

I raised that because when people do that exercise at coaching, they're often surprised at how well it worked out when they went outside their comfort zone. And it gives them more compliments in power when they realized that, "Oh, even though I'm doing this business for the first time, there have been a number of times from the time I was a kid until maybe in the last few years where I've done something that made me really uncomfortable," and then you ask, "Well, do you regret that you did it?" And almost always the answer is no, unless it turned into an unmitigated disaster.

Deb Zahn: In which case, now you have a good story.

Steven Cristol: Exactly.

Deb Zahn: Yeah, it's interesting. When I read that piece, I recall, I'm one of those people who had the dream of a country life. I was going to go out in the country and I was going to raise chickens and have a little mini farm, which I have by the way. And.

Steven Cristol: See, that's amazing. That's amazing.

Deb Zahn: But I remember saying to my husband, I have a tendency to overwork, and what I don't want to do is move to the country for the peaceful life that comes with me and I bring that same sort of chaos that that created with me. What we did is we sort of balanced it with. "Yes, but you're also very self-reflective. And yes, you're also a problem solver. So, if you see yourself doing that, which you probably will do, you're very good at figuring out solutions." And so we kind of kept balancing it until we thought, yeah, this actually makes some sense.

Steven Cristol: Well, I think it worked out for you. That is great.

Deb Zahn: Thank you. Yeah. And sometimes I don't pick my tomatoes soon enough, so that just happens. I'm OK with that.

Steven Cristol: Well, it's always compromises whether we are self-employed or not, right?

Deb Zahn: That's right. Well, one of the things that struck me when I first started the book, your first chapter, I felt like I had to look around my house to see if you had bugged it, which is, don't assume your new boss is better than your old one. I'd love to have you dive into that a little bit more and talk about what does that mean for choices related to going independent.

Steven Cristol: Well, it actually intersects with a later chapter on perfectionism because the more you're perfectionist tendencies, the tougher boss you are. And actually a tougher and more unreasonable boss you are likely to be. So, I actually spend a lot of time on both of those things because I found them to be... And this is a little bit confessional, but I found them to be so inextricable that they sort of had to both be dealt with because I thought I had demanding bosses until it was me, and I was relentless, and I was unreasonable. There was very little mercy in the first couple of years. It's hard enough in the first couple of years.

So, self-compassion becomes really, really important. And it's something that you kind of discover both as you get older. But hopefully don't wait until you're older if you're just starting out to really think about that every day. I mean, later in the book I talk about things like consciousness and meditation and other ways to stay in touch with the softer skills that are required when you're bossing yourself around. That's a big part of it. And just finding that balance between not being unreasonably demanding and perfectionist and doing fabulous work. It's a very fine line. It's easy to set the bar too low for some people too. I had coaching clients who said, "I really exceeded my goals last year," and it turns out their goals were less ambitious than they really could have been for a person of that level of talent.

Deb Zahn: Yeah. Yeah, yeah, yeah. I love that. I actually will sometimes joke and I'll say, "My boss sucks." And I'm my boss, which means I need to pay attention to what I'm doing. So, that whole chapter in the one on perfectionism, which guilty is charged, very powerful. I really like also that you hit upon, and again, I'm not hitting all of the gems in the book, but making discipline choices among many paths. Because a lot of folks, even after let's say that they've even said, "Yes, I want to be an independent consultant," there are many paths that someone could take to doing that. And often it's a place where I see that people get lost because either they think "I can only do one thing," and they don't even see that there's many paths or, "There's so many paths. I can't choose." And you have a really, I found, simple but sort of helpful three step process to move through that. Can you share that with folks starting with the identify?

Steven Cristol: Sure. Well, I talked earlier about drivers of satisfaction. I never care whether a client calls them drivers of satisfaction or drivers of happiness or drivers of fulfillment or drivers of meaning or drivers of joy. You get the idea. What are the things that are going to make you fulfilled and productive in independent work? And so the first thing is identifying those things, those needs that you have that really matter and what they are. Some of them will be concrete, like financial security, although that has some abstract aspects too. Some of them will be very abstract, things that are about aligning with your values, things about more control. Those things need to be identified. And I find that there'll usually be somewhere between five and 10 of those needs, if you will, or drivers of satisfaction that account probably for 90% of how things are going to turn out. You could have a list of 20 or 30 of them, but most of them are noise and really aren't going to make or break you. But those five to 10 probably will make or break you.

Step one is to identify what those needs are. However, before you can prioritize those needs because they're not all equally important, you have to know what you're prioritizing. So, they need to be unpacked. I spent a fair amount of time in the book talking about how do you take an abstract need and make it more concrete so that you know what you're evaluating because where we're going here in a minute is actually scoring alternatives on these drivers of meaning or drivers of satisfaction.

And so when you start to say, "Well, I want more control," control over what? Do I want control over my hours? Do I want control over who I work with? Do I want control over what the work is? Do I want control over who I partner with? More control over work-life balance? And oh, and there's another one, work-life balance. What does that mean to you? What's going to feel balanced? Is it just about hours a week or is it how you're spending them and how you're spending the hours that you don't consider work?

So, once you unpack these things, when I say step one is identifying, step two is define. When I ask people to define their drivers of satisfaction, they say, "Well, I already identified them," I said, "Yeah, but you didn't define them. We have to unpack those." They all have component parts. And I actually learned this from optimizing product roadmaps for companies because if you look at something like... I think one of the examples in the book from one of my clients was portable wireless speakers for audio. When somebody says, "It's got to sound great," well, what does sound great mean? It means deep bass, clear vocals. I mean, there's seven or eight things that constitute great sound, just like there're some things that constitute cool design. These are abstract concepts, but they have concrete pieces.

And so it's very important with these drivers of satisfaction for consultants in independent work to know what those drivers are, to define them adequately so you know what you're evaluating and prioritizing. And then comes step three, which is prioritizing their relative importance. They're all important or they wouldn't be on the list, but some might be two or three or four times more important than the least important one.

And so in the book, again, much like I do with products, when you're prioritizing these, you can assign a certain... Imagine allocating 100 points in a pie chart to seven things that really matter to you. One of them might get 25 points, and one of them might only get five or 10. So, that once you rate how well a particular path to independence for a particular kind of consulting work stacks up on each of these seven, let's say at seven, drivers of satisfaction, you can multiply those scores by the relative importance of the driver. And ultimately, it's going to tell you, you have just taken a bunch of informed subjective inputs, turn them into quantitative outputs, and you now have some metrics that basically say, "This is a better fit for me. I'm likely to be more fulfilled at this."

I've had clients where they score their current... I always advise to score your current job if you have one against your alternatives, so you know what you're potentially giving up. What we'll find sometimes is that if all of those drivers had been treated equally, their current job would win. But when they weigh the most important drivers, they actually find out that going into the internet business with their best friend was a better choice for them.

Deb Zahn: Interesting. So, I love this. I also love scoring things. I do that in my personal life, I can't help it. But what I love about it is it made me think about, and I want to give a concrete example, I keep talking about wanting flexibility as being independent. That's one of the things that I truly, truly love about the independence. But what do I mean by that? I realize I don't have a metric. I don't have really something very well-defined. I know that it would rise to the top of the list. I realize my metric this year would actually be, essentially of the times that my 82-year old mom wants to go kayaking, 80% of the time can I go with her regardless of what time it is, regardless of what day? And if I can only do that 5% of the time, then I don't really have that flexibility that I say is so important to me.

Steven Cristol: No, that's a great example. And actually you probably saw in the book somewhere me referring to kayaking on Tuesdays when I can have the ocean to myself.

Deb Zahn: That's right. I just added an 82-year-old mom, but otherwise, yeah.

Steven Cristol: Right.

Deb Zahn: I realized that that's probably how I would define that because it has meaning to me and it's a good canary in the coal mine if I'm working too much that I don't really have that flexibility. So, that's wonderful.

So, I want to skip ahead because there's a lot of other great things that come in the book, but one of the things that I thought was so important that you mentioned that people have to think about is making it work for the long haul, just how you describe it. So, it's not, I become independent, and Shazam! And then you haven't thought about what does that look like in three years, what does that look like in five years. So, how do you help people think about that long-haul type of approach?

Steven Cristol: Sure. It's such a personal thing and everybody needs to do this in a way that they're comfortable with. I've actually just found that a lot of it came later in the second half of my consulting career, that it was felt so counterintuitive in the first half to do things like rest.

Deb Zahn: Exactly.

Steven Cristol: And then I actually studied quite a bit, both for my last book and the new one. I studied quite a bit of worldwide data and research on stress and disease and sleep, and a lot of the things that really do determine performance. On the one hand, it's just very counterproductive when a lot of people think, "Well, the more hours I put in, the more productive I'm going to be," especially when they're starting their own business. If you look at the statistics, it's really interesting. If you look at countries like Ireland that have three times the GDP per person that some countries have work longer hours than they do, United States is seventh among the 37 OECD countries in terms of GDP per person. And we work more than almost anybody except some countries in Asia. So, there is not a correlation between, let me make this very clear, between hours and productivity. And in fact, there is often an inverse correlation.

And so you have to find a rhythm. It's especially hard in that first year or two when it's just all on you and the money's not coming in yet maybe and you're feeling all these pressures to prove that you can actually do this. So, it's so hard to let up. But you can get away with that for a while. Sometimes it's sort of required. But for the long haul, I mean, I wouldn't still be here if I worked for the last 20 years the way I did for the first 10.

So, I talk about resting. I talk about meditation because, again, it's a personal thing that happens to work for me. Some people, when I mention meditation, they think, "Oh, that means I've got to find an hour or somewhere to sit in front of an altar." That's not what I'm talking about. Sometimes you can do a five-minute mini meditation at your desk and it will refresh you and get you unstuck from whatever you're working on. But I do that every day and I do it a little bit in between.

And then I talk about consciousness as distinguished from the mindfulness that you get with meditation. Consciousness really is more about being purpose-driven, really staying in touch with why do you do this work, how you are helping people, how does that feel. Get a lot of power from reminding yourself when you're making clients successful and happy, which is a pretty good reason to be a consultant, when you're doing that, we get energy from that. I know you do. And then there's the whole aspect of being purpose-driven in terms of, I like to think companies, we all need a social license to operate. Are we doing anything for the greater good? I talk about that a little bit more in the next to last chapter. And then I think really that kind of spilled over into really talking about how working independently, we talked about flexibility, how it can be a gateway to a larger life.

Deb Zahn: Yeah, I loved that phrase. I actually have it written down to ask you about because what a great way to think of it as a path to opening things up. So, describe what you mean by that.

Steven Cristol: Well, what I mean by that is we can't all be Leonardo da Vinci, but I have this belief really just about anyone has a polymath in there somewhere that's dying to be excavated. I think it was Walt Whitman and Leaves of Grass who said, "I am large. I contain multitudes." Well, we all contain multitudes. Sometimes our work isn’t big enough to encompass all of those multitudes. And so, one of the great things about independent work is having the flexibility and the leverage to pursue other passions, pursue other talents, whether that's kayaking or whether it's music, or whether it's volunteer work or all the above. And much like, rest, instead of taking away from your independent consulting success, it completely nourishes it, not just because of the energy, but... I don't know about you, but I've gotten some of my best ideas in a kayak under Tuesday afternoon for a client, or walking in the woods. So, all of it pays back, and you're using different muscles, you're using different creativity, you're using different parts of your brain. It all comes back and nourishes what you're doing for clients.

Deb Zahn: Absolutely agree. I was trying to solve a problem for a client once, and I couldn't think of how because it was just dicey and there were too many missing parts. So, I took a break and I went to my garden and I was picking beets, and suddenly it occurred to me, "What if they did it this way?"

Steven Cristol: There you go. That's exactly what I'm talking about.

Deb Zahn: If I'd been staring at a computer or stuck in a meeting, I don't know that it would've come to me.

Steven Cristol: That's right. So, you have to be able to disassociate from the guilt reflex that, "Oh, I'm not working right now." So, that's a lot of what I meant by a larger life. And I know for me, I have no way of knowing how happy and fulfilled I would be if I were only doing my consulting work. Obviously, it's been the center of the enterprise. When people ask me what I do, that's what I do. But without those other things, I purposely like those lines to be blurred. I never like to think of work and play as being two totally separate things. And so a lot of the battle is blurring those lines so that you can't really tell for sure where one leaves off and the other begins.

Deb Zahn: Yeah, yeah, yeah. Which, if well managed, can be a beautiful, beautiful thing.

Steven Cristol: Yes, there is the potential for mismanaging it, that's for sure.

Deb Zahn: So, we've hit upon so many of the fabulous things there in the book. And by the way, I am going to take your little assessment and do my scoring. I'm absolutely doing that.

Steven Cristol: OK.

Deb Zahn: But if folks want to dive into this because they're either thinking of being independent or they are, and it's not exactly looking the way they want it to look, where can they find you?

Steven Cristol: Oh, well, they can find me in two places. My company's website is Strategic Harmony. It's S-T-R-A-T, hyphen, My book website for the new book and coaching is So, And that's probably the first place I would go because there's also... I did a pretty carefully curated resources page for independent self-employeds, organizations, publications, events, things with links to all of those places. And so I'd like to think that that could be really useful for someone who's either recently self-employed or considering doing it.

Deb Zahn: Wonderful. Wonderful. So, let me ask you this last question. We've actually probably hit upon some of the things that you do, but how do you bring balance to your life however it is you define that?

Steven Cristol: Well, for me, a lot of it is those other passions. The nice thing is in the beginning, it's so all consuming when you're setting up a business. Realistically, is less time for these other things. But if you just stay with it for the long haul, things really start to open up. And when they do open up, you find it, you get to do all these other things. Like you, I love kayaking. I'm a singer-songwriter, I love performing in coffee houses. When I was a boss, I used to tell people that worked for me, "If you want to learn how to prepare information for senior executives, learn how to write a song because you only have 150 words for a beginning, middle end, and character development and a climax." And it turned out to be a pretty useful exercise.

Deb Zahn: Oh my gosh, I love that.

Steven Cristol: That's just one example of how these things inform and nourish each other. So, when we talk about a larger life, I can't think of a better ticket to a larger life than independent work if it's managed reasonably well and if you're doing it for the right reasons, and you know what your drivers of satisfaction actually are.

Deb Zahn: Wonderful. Well, Steven, thank you so much for being on the show. I really appreciate it. And I do encourage folks who are independent consultants to go check this book out because there's a lot to dive into that's going to make the experience better for you.

Steven Cristol: Thank you. Really nice to be in conversation with you. I've been watching your work for a while.

Deb Zahn: Thanks so much for listening to this episode of the Craft of Consulting podcast. I want to ask you to do actually three things. If you enjoyed this episode or you've enjoyed any of my other ones, hit subscribe. I got a lot of other great guests that are coming up in a lot of other great content and I don't want you to miss anything.

But the other two things that I'm going to ask you to do is, one is if you have any comments, so if you have any suggestions or any kind of feedback that will help make this podcast more helpful to more listeners, please include those. And then the last thing is, again, if you've gotten something out of this, share it. Share it with somebody you know who's a consultant or thinking about being a consultant, and make sure that they also have access to all this great content and all the other great content that's going to be coming up.

So, as always, you can go and get more wonderful information and tools at Thanks so much. I will talk to you on the next episode.

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