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Episode 129: The Benefits of On-and-Off Consulting—with David Wolpert

Deb Zahn: I want to welcome you to this week's episode of the Craft of Consulting podcast. This podcast is little bit different. I'm going to be talking with someone who toggles back and forth between being a consultant and then being employed, and then being a consultant, and then being employed. And I was so excited to talk to him about this because it hadn't occurred to me that this can be a really viable career option. And there can be tons of benefits, not just for you in your life but also for the people that hire you, either as an employee or as a consultant. So I brought on David Wolpert, who this is what his career has looked like, and he's going to talk about what that means and what the benefits have been to being able to build his career in exactly that way. So great stuff on this podcast. Let's get started.

I want to welcome to my show today David Wolpert. David, welcome to the show.

David Wolpert: Thank you, Deb. It's great to be here.

Deb Zahn: So let's start off. Tell my listeners what you do.

David Wolpert: Well, the timing of that question is fantastic because you're catching me just at a point of transition. So currently, I am a content marketing consultant for B2B technology companies, but just yesterday, I accepted a job offer to work for a software company full time, doing content development and content strategy. So I'll be starting that next month, so there you go.

Deb Zahn: All right, well, and that's what we wanted to talk about because you've had a really interesting journey as a consultant that is actually a viable option for folks to consider. So can you say a little bit about how this isn't your first transition back and forth, what that looks like?

David Wolpert: Yeah, this is actually going to be the third time I've gone from being a full-time consultant to being a full-time employee. And each time has been a sort of different scenario, but there are a lot of commonalities. So the first time, just to set it up, I had fallen into consulting quite by accident, or without intention, as many of your listeners probably have too. I was working for a software company full time, and there was going to be a reorganization, and I didn't like how I was going to fall after that reorg into that new organization. So I was open to leaving, and I just said, "You know what, maybe now's the time." I was thinking about leaving anyway. I didn't have a plan in mind; I just said, "You know, I feel like I should be doing something else, so I'm going to exit now."

And so I left the company without a plan of what I was going to do, and I started to do some travel. I started to do some home renovation work. You know, just catching up with friends, this kind of thing. And kind of out of the blue, I got a call from a woman I used to work with at another company who said, "Hey, we really need a white paper written, and it just so happens there's no one on our team that has the skill or the bandwidth to do that. David, would you like to do it?" And I didn't think about it very long; I thought, "Yeah, I mean, I like to write, I've done white papers before, I have nothing else to do, and this is a quick way to make some cash." So I said yes. And then, shortly thereafter, I got a call from another person I used to work with who said, "Hey, we need some competitive intelligence work done. Would you be interested in doing that?" And I said, "Yeah, sure."

So I did that, and then I got a third call from a friend who said, "Hey, we need an eCommerce strategy. Is that something you can help me with?" And I said, "Sure." And so it hit me just then that what I was doing was consulting. I didn't set out to do that. I didn't seek or want to do that, necessarily. But all of a sudden I found clients coming to me. The work was interesting, the pay was good, so I said, "You know what, let's just stick with this." So that's how I became a consultant the first time.

So a couple years go by, and things were going well on the consulting front. I wasn't quite making what I wanted to make, and that was really my fault for not really having a system to how to grow my own business. But I saw a job opening at yet another software company, and it was one I knew well. I'd applied there years before. They were in the publishing industry, which just interested me sort of personally and intrinsically because I had self-published three books in a past life. And so this was a company that was digitizing books in this new ebook market, new at the time. And so I thought, "You know, that could be fun. It's something I've always been interested in. The company's growing. Why not send my resume in? What is the potential harm in just saying I might be interested?"

So I put my resume in the hat. I got a call back, and one thing led to another, and I was hired. And so I went back to the full-time world, was there for a year, and then that company had some financial issues and I was laid off, and I went right back to consulting. Right where I picked off...sorry, left off. And it was really easy to get back in, and I just started doing it again. And this time I was far more successful as a consultant. I sort of knew what I was doing, I had some streetwise ideas now.

And things were going well, but then, once again, I saw a job open up. I said, "That sounds like a dream job," interviewed there, and sure enough, I got hired to be a chief content officer at a new marketing agency, and had a really good three-year run there, and left to go work in the solar industry, which is a personal pursuit of mine. Went from there to work for IBM, long story, and a similar thing as happened years prior, working at IBM, I realized I wanted to do something else, and left IBM, started traveling the world, and then I was in Asia when COVID hit, and…

Deb Zahn: Ruh-roh.

David Wolpert: Yeah, and had to end my world journeys. I came back to home to Austin, and out of the blue, a former client of mine called me and said, "Hey, we got some work. Are you still doing this consulting thing?" And I said, "OK," and so I'm back in the game again. That's how I ended up here.

Deb Zahn: Wow. And then you just are about to make the transition again.

David Wolpert: Exactly. And this setup, again, I wasn't really looking. A friend of mine from my IBM days had gone to this new company. He loves it there, and he heard through the grapevine internally that a woman was looking to hire someone exactly like me, my skillset. And he said, "You know, you should talk to my friend David," and so before the job posting was ever posted, before the job description was ever written, she called me, and things went well. I met the rest of the team and she made me an offer, and it was an excellent offer in a lot of ways, and I loved the team. And again, it was a question of, why not pursue this opportunity? It all sounds great. Consulting is great too, but this sounded even just slightly better to me at this time in my life, so I thought, "Why not lean into that?"

Deb Zahn: How do you decide? What criteria are you using to decide when you want to do consulting versus when you want to actually be employed, other than, "Oh my gosh, it's a dream job, this looks fabulous"?

David Wolpert: Yeah, you know, it's not one thing. I don't really have a checklist or a framework to make that decision. For me, it's always been very much what feels right at this time in my life, right? Like, anyone who's thinking about consulting, there's a lot to like about it. You can be your own boss, you can pick your own clients, you can pick your own working hours, you can set your own rates. There's a lot of things you can do, a lot of flexibility. The downside is, as I'm sure many of your viewers can relate to, it's tough. It's tough to be your own business. You always have to be finding the next client.

And for me, this most recent move, it had a lot more to do with the predictability of income than the total income potential, you know, especially...This is especially true in the creative services field, where I live, where...And especially if you're working with tech companies, where things move very quickly. Tech company priorities shift constantly, businesses come and go, people come and go, projects and priorities come and go. And in that kind of environment, you never know if the client you have today will be your client next month, through no fault of your own in many cases.

Deb Zahn: Yeah.

David Wolpert: And so I often have months where, as a consultant, I'm making great money, things are looking good, more projects are coming my way, and then the next month, it may be zero. And just from a personal budgeting perspective, it makes life more challenging. And right now, right here, at this point in my life, I value the stability more and the predictability of income. I'd rather not spend so much time constantly selling and looking for the next client; I'd rather just focus on delivering my services.

Deb Zahn: It sounds like, though, you also got better over time at the consultant side of it. So at the beginning, things just showed up. What did you have to learn to make it work when you were a consultant?

David Wolpert: Wow, a lot. So one thing early on I was bad at was managing my clients, that...You know, I just assumed that if they're going to engage me, that of course they will check their calendars, attend every meeting, pay my invoices promptly, follow up immediately when I need them to. And, of course, none of this happened. And so I got a lot better at project-managing my clients themselves, reminding them of upcoming meetings, reminding them of the importance of certain deliverables and their timely attention to things, and this kind of stuff. So that was a big one.

The other thing that I had a long learning curve on was pricing my services to value, not to time. And so I made the classic mistake often of saying I charge by the hour, but the fact that it takes me only one hour to do something has nothing to do with the actual value it delivers. So I got better over time at pricing my services accordingly. But yeah, those were long ramps. I'm still not perfect at those things, but I'm much better.

Deb Zahn: That's great, that's great. Now I can imagine toggling back and forth between consulting and employment has benefits, so there's things that it does for you to be able to go back and forth between two...What do you think is the biggest benefit for you?

David Wolpert: What some employers have actually told me about my experience that they find valuable, and I agree, one is that they like that I've worked with so many clients on so many different kinds of problems in so many different industries, so that variety lets me hit the ground running at any new company very quickly, and they like that. I once counted that in all, I've worked with well over 100 companies, either on their payroll or providing services to them, and in all different industries. Mostly tech, but some have been in things like the insurance side of technology. So I've seen a little bit of everything, and I think every employer values that.

Consultants tend to be better at what I call the mechanics of business. They all know, for example, how to sell because they've had to; otherwise, they don't eat. And so when you're a consultant, you've got to spend some time learning how to sell; if you don't, you will have no clients, and things will go south quickly.

Deb Zahn: That's right.

David Wolpert: But consultants are also better at things like legal issues. They often have to come up with their own contracts and review contracts. They understand accounting better for their own business. I think they understand tax issues because they have to work with an accountant or do their own taxes. And so those things really help when you walk into any business, and you understand the legal issues, the accounting issues, and some of the finance issues.

I think most importantly, employers like that consultants are creative. They're builders, they know how to run a business and often are very scrappy about doing that, in a good way. And they've taken some risks by quitting their day jobs and trying their hand at running their own business. And that says a lot about you individually as well as professionally, and so I think those are all very true, and all things I think employers have told me about me that they find valuable, but I think it's true for anyone in consulting.

Deb Zahn: Yeah, I kept picturing a Swiss Army knife as you were describing that. As opposed to you've been in one place, you've been there for however many years, you know how that place works and operates and functions, but if you're a consultant, you have to get up to speed very, very quickly on all sorts of things with new clients: culture, ways of working, new systems that they have, and a whole host of other things that just makes us able to adapt, I think, very, very quickly because we've had to.

David Wolpert: Yeah.

Deb Zahn: So what are the downsides?

David Wolpert: So it depends on the individual. It depends on the company you might be going to. I do think there's two things that are worth being aware of and that need to be managed. One is that your resume may look discontinuous if you've been a consultant and are coming back to the full-time world. And this is an issue of, I think a lot of recruiters, with all due respect to recruiters, I mean, they often are looking at a checklist, and they're looking for people who have obvious career progression. So they want to see someone who was a manager, and then a senior manager, and then a director, and then a vice president, and so forth. And so if you're a consultant, especially if it was for years or a decade or more, they see this break in your resume, and that can obviously interrupt your career progression, and some recruiters can't really see past that.

Deb Zahn: Yeah.

David Wolpert: So I think it's one of these things where if you can get to the hiring manager, you can explain this. I think most hiring managers will understand and be impressed by it and not hold it against you. Some recruiters might, so you need to be careful of how you present it on your resume and who you present it to. And related to that, I think there's another issue of recruiters or hiring managers potentially pigeonholing you as someone who's not serious about work, who might go back and forth or can't make up their mind. But again, I think these are always things that can be explained. It's just an extra step you need to do as a would-be jobseeker now to explain it, but it's something to just keep an eye open for and manage.

Deb Zahn: I think that's helpful. And is there any sort of tips or tricks you've found particularly handy in either getting past the recruiter or explaining it in a way that they see it as a benefit and not as a, you know, "This dude's a flake," which I think is sometimes what they experience?

David Wolpert: Yeah, so we could do a whole different podcast on how to get around the recruiter and get right to the hiring manager, but...You know, if nothing else, I do think on your resume, you need to talk about the things that you learned, the skills that you mastered, the things that are transferable and applicable to your new potential employer, and make it not sound like you were just freelancing it, which has a negative connotation, but that you were adding real value for your clients in a relevant industry, that you've learned a lot, and that you can take those same skills, the same kind of qualities, and apply it at your next job.

Deb Zahn: That's great, so developing that clear value proposition, which is exactly what you have to do when you become a consultant, is clearly define how all of the employment that you've had, or the past consulting gigs, actually make you extremely valuable because again, we can do the Swiss Army knife thing.

David Wolpert: Exactly. And I think it helps, I mean, as with...Whether you're a consultant or looking for a full-time job, you need to have a story, right, a narrative about you. There was a book years ago called The Brand Called You. Same idea, that there needs to be a way you can articulate at an elevator-pitch level what you do, what value you bring, what you've learned, why you're at where you are professionally, this kind of thing. And I can't say that I've done a great job at doing this, but I think it's a great goal and thing to keep in mind of, what is the story you're going to tell your next employer?

Deb Zahn: I love that. I love that. So if you were talking...I'm actually going to ask sort of this question in two different ways. The first is from the perspective of someone who's leaving employment to go become a consultant for whatever reasons. They got laid off or, like you, they're like, "Eh, I really feel like doing something different." What would you tell them, "Absolutely do this" or "Absolutely don't do this"?

David Wolpert: Absolutely make sure that you're not burning any bridges. Often, that company you just worked for can be your first client as a consultant. And you definitely want to mine your professional network, everyone you've ever worked with; they can all be potential clients of yours. And let people know that you decided to leave that world, perhaps temporarily, and go out on your own, and tell people exactly what you're doing and what kind of clients you're looking for. And if people know what you're looking for, they can potentially help you find your first few clients, which is invaluable.

Deb Zahn: So it sounds like you have to gain that clarity first, which I'm sort of saying rhetorically. How did you get clarity about who you wanted to work with?

David Wolpert: Great point. So I knew I wanted to work with business-to-business, technology-driven companies because that was the world I came from. It was what I knew the best, it's where I knew I could add the most value, as opposed to, for example, the business-to-consumer side. I knew I couldn't help a restaurant with content marketing. Not that I didn't know how, but I'm not the right guy; there are better people than me to do that. So you need to be a little humble and say, "This is not what I'm really going to be good at," so probably avoid that. So have some broad parameters.

But to your point, I originally set out to be a product marketing consultant, which is similar to content marketing, but most of my job titles had been Product Marketer. And so what I initially branded my company, and it was called Swordfish Communications, Swordfish was a product marketing consultancy. But what clients began to tell me they valued most was not all the different product marketing skills that I had, but one specific one, which was that I was really good at writing the kinds of things that product marketers wrote. And so the clients guided me into focusing Swordfish onto things like developing white papers and case studies, and away from things like competitive intelligence work, which I was very good at, had a lot of experience doing, but that's not what clients valued the most from me specifically.

And so rather than try to correct that or steer that in a different direction that I thought I wanted it to go, I let my clients tell me what they wanted me to do, and so I began to morph it into a content marketing agency, and that...I'm glad I did it; I think that made the most sense. But you'll never know going into it exactly what you're going to do or the bounds of what you're going to do. You have to do some trial-and-error experimentation there.

Deb Zahn: And it sounds like because of some of your past experience, marketing was a little bit easier because you at least knew what it was and what it meant.

David Wolpert: Sure.

Deb Zahn: How were you able to, particularly as you got better at the consulting side and the business side of consulting, apply some of those skills? Because I know that's baffling for so many consultants who, when they first switch from corporate or switch from wherever their work world was, they're now marketing themselves; that seems strange. So how did you sort of take what you knew and apply that to yourself?

David Wolpert: Yeah, so I'm very unusual in this way, in that I never really marketed myself at all. I got 100% of my clients through referrals, just word of mouth. And that was doable only because I had a very strong professional network, and as I mentioned earlier, I constantly let people know what it was I did, and so they could find companies for me to work with. So I was very fortunate in that way.

The little...I guess you could call it marketing. I did a little bit of outreach myself. I call that more selling than marketing, where, for example, one of my biggest clients ever, I found because I read a newspaper article that a company was relocating from San Francisco to Austin, and I simply found the CEO through LinkedIn and sent him an InMail note and said, "Hey, congratulations on your move. I think you're going to love Austin. Here's what I do. Would that be valuable to you? Because I know you're hiring for that right now, and I'm not necessarily looking for a job, but I'd love to give you some pointers on the Austin market. I know you're looking to hire a lot of people; I might know some people who would be valuable to you. I could make some recommendations. Do you want to have coffee?" And it was that simple. And he said yes, and we had a coffee meeting that turned into them being my biggest client of all at Swordfish.

And so, that is a form of selling. It's a very soft sell, a very soft approach. That is probably the most I've ever done in terms of actually marketing myself. The rest were simply, again, word-of-mouth referrals, and I was very fortunate, that was enough.

Deb Zahn: That's great. Well and I think the network piece is so critical because often, so many people neglect their network, and then only reach out to them when you need something. How do you keep in contact, whether you're employed or you're a consultant, so that your network has some freshness to it?

David Wolpert: It's hard. It's really hard. I think you need to ping people occasionally without a purpose in mind, just to say, "Hey, how's it going?" It's especially great to do that when you see through LinkedIn...I love LinkedIn, it's a great resource for me. But when I see people move from one job to the next, that's a great time to send them a note saying, "I see you moved. Sounds like a great position. How are things going?" And just check in. And so, just a soft ping like that, of just keeping on top of who's moving where, and just saying hi once in a while, that can be enough.

But I would say, to emphasize a point I made previously, it's really important that people in your network know what you're doing and what you're looking for. I'm approached all the time by job-seekers who say, "Hey, I'm looking for a job in marketing. Can you help me?" And I always say, "Well marketing is a very big field. What specifically do you do?" "Oh, I do anything." Well no. What specifically do you do, or what do you want to do? And it's OK not to know, but no one can help you if you don't. And so you need to think about exactly what, and so I would tell people, for example, "If you know of any tech companies in the B2B space, such as," and give some examples, "that need help with content marketing specifically, I would appreciate a referral." And so that was very helpful. The more specific you can be, the more your network can help you.

Deb Zahn: I love that. Yeah, so I'm in healthcare, and if someone says they want to be a healthcare consultant, I'm like, "Well what on earth does that mean?" I've found that it often frightens folks to narrow down enough to define it, as if that means that they're not going to get clients, as opposed to understanding it as, it has to be actionable for the people you're asking help from, otherwise they're not going to know who to send anything to.

David Wolpert: Exactly.

Deb Zahn: I love that. So if someone is interested in the toggling back and forth, so they like being a consultant, then they might want to be employed, and back and forth, any advice you would give them, as that is a truly viable option for having a career?

David Wolpert: It's always a viable option to toggle. Again, think about how you want to position yourself to employers in terms of what you did as a consultant. So go through that sort of personal branding exercise. And here's where a career coach or a life coach or a mentor can really help you sort of objectively frame what you did as a consultant and what you want to do in the full-time world. So just think about that story, that narrative that you're going to tell. That's the biggest part for me. Think about how to avoid serious gaps in your resume, just to keep it cohesive, to tell a story that doesn't sound like you don't know what you're doing, but rather that you know exactly what you're doing, but you're doing it with intention, not by accident, and not because you have to, but because it's a choice that you make. And I think if you can do that and keep that right frame of mind, you'll be fine.

Deb Zahn: I love that, and I love the "really be clear about what the story is." Because the recruiter is going to have a story in their head, you have to replace that with yours, which means you better show up with a really clear and compelling one.

David Wolpert: Exactly right. Exactly right.

Deb Zahn: Oh, that's wonderful. So where can...If folks want your help doing exactly what you said you do, if you're ever a consultant again, or if they're looking to employ you, where can they find you?

David Wolpert: So I do have a website. It's not a great one,, and that's me.

Deb Zahn: That's great. Now, I always ask this question because...And I'm particularly interested given some of the toggling you do in your career, but...And I know how cool Austin is, so there's a lot of...I've been there many times, so there's a lot of cool things to do. But how do you bring balance to your life, however it is you define that?

David Wolpert: Yeah, it's a great question. I feel like my life naturally has pretty good balance as is, in terms of integrating my work life, my play life, and just the parts of life of just doing everything we need to get done, like doing the dishes.

Deb Zahn: Oh, those.

David Wolpert: Yes. I think it's pretty well balanced, but I do think it's important to find a way to stay centered and grounded in life, just to be objective. And so for me, that's connecting with nature, and so I need to be in or around nature on a daily basis. And on a day-to-day level, that could be anything from just taking a walk around the lake on a nice day, it could be picking up litter on a trail that I'm hiking, it could be doing some gardening. Just anything that connects me with nature, it really helps.

More ambitiously, I try to take two trips a year or more to somewhere with just overwhelming natural beauty. Favorite places are...The US national parks are incredible. If you've never been to southern Utah, by all means go. Or to...I also love islands, especially the North Atlantic. There's something about that part of the world, I love it. And when I go to places like that, I'm just overwhelmed by beauty, and it gives me some space to think about my life and what's important in work, what's important in the rest of my life. It gives me some perspective. And so that for me is the balance I need, and so nature really answers that for me.

Deb Zahn: Oh, that's wonderful. Now you're going to indulge me a little bit, simply because...Now I know you're good at networking because I know one of the people in your network, which is how we met. So you've known my brother for how long?

David Wolpert: We met in 1997 at grad school, in the MBA program at the University of Texas.

Deb Zahn: Oh, that's so fun. Yeah, so he introduced us, which is a lot of fun. And I will tell you, he will listen to this podcast, and he will listen to this podcast not because his sister did it, but because you were on it.

David Wolpert: Mm-hmm, sure.

Deb Zahn: So the one thing that I know about, his name is also David, is for some reason, it drives him crazy that I mention cats on my podcast. He finds it weird, a little baffling, he's not sure why I do it. And because I am a bratty little sister, no matter how old I get and how gray I get, I can't resist. So I appreciate you indulging me, this is for my brother: cats, cats, cats, cats, cats, and more cats. I'm going to make him listen to the end so he can hear that, and then we can both imagine his eyes rolling.

David Wolpert: I can see them now, they are rolling.

Deb Zahn: Exactly. So thank you for indulging me in playing that little joke on my poor older brother.

David Wolpert: Of course.

Deb Zahn: But David, thank you so much for joining on the show. I had not really thought of this, as many consultants as I've worked with, as a potential path for someone to enjoy consulting when they enjoy it and enjoy employment when they want to do that. So I appreciate you putting out this as a path that folks can take.

David Wolpert: Absolutely, it's a path anyone can take, and there's no harm in it. It's a choice, it's the right choice for some people at the right time, and I just encourage everyone to do what they need to do to live the richest life they can lead.

Deb Zahn: That's best said, thank you so much.

David Wolpert: All right, well, thank you, Deb. I really appreciate it. It's been an honor being here.

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 if you've enjoyed any of my other ones, hit subscribe. I got a lot of other great guests that are coming up and 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. Bye-bye.

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