TCC Podcast #41: Jenny Blake

Author, coach and career change expert, Jenny Blake, joins Rob and Kira in The Copywriter Club Podcast studio this week to talk about why she organizes her book shelf by color : ). We also talk about her book, Pivot: The Only Move that Matters is Your Next One. But this isn’t just a pitch for Jenny’s book. She walked us through the process but also talked about:
•  How to figure out your strengths then determine where you want to be a year from now
•  How to scan the horizon for opportunities, people, and skills that might take you to the next level
•  How to experiment with your pivots to eliminate risk and find things that work
•  How to deal with your inner CFO who says, “you’re out of your mind” to try something new or different
•  The “Do, Drop or Delegate” formula for staying engaged in your work
•  Why you should create scalable streams of income as part of your business, and
•  How to build a platform so you get noticed

If you’re thinking about changing careers to become a copywriter, or want to explore a new niche, or simply want to make sure you’re on the right career track, this episode is a must listen. Click the play button below, or scroll down for a full transcript.

The people and stuff we mentioned on the show:

Sponsor: AirStory

Life After College
Pivot Method Tool Kit
Actionable Communications
She Can Coterie
Stand Out by Dorie Clark
Harvard Business Review
Fast Company
Huffington Post
Book Yourself Solid by Michael Port
David Moldawer
Ramit Sethi
Marie Forleo
Daily Rituals by Mason Currey
Delegation Ninja (use the code TCC to save $100 or just click here)
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity

Full Transcript:

The Copywriter Club Podcast is sponsored by Airstory, the writing platform for professional writers who want to get more done in half the time. Learn more at

Rob: What if you could hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes and their habits, then steal an idea or two to inspire your own work? That’s what Kira and I do every week at The Copywriter Club Podcast.

Kira: You’re invited to join the Club for episode 41, as we chat with author and career strategist Jenny Blake about her Pivot Method and what it means for copywriters and others who might be wondering what’s next, leaving Google to start her own business, dealing with burnout, and whether she really organizes the books on her shelf by color, not subject.

Rob: Hey, Kira. Hey, Jenny.

Kira: Hello.

Jenny: Hey, thank you so much for having me. Yes, indeed, I organize by color, but I will tell you, I know where every book is because the color imprint stays in my mind. It’s really easy to zoom in, like, “Oh, yeah, that was a red book, it’s over here.” It’s not as confusing as you might think.

Rob: I think a lot of writers, if they go to your website, they’re going to see the video or the pictures that you’ve got of your bookshelf. That’s one of the first things, I’m like, “Oh my gosh, all of the white books are together.”

Kira: I know. I love it.

Rob: “All of the green books are together.”

Jenny: Oh, yeah.

Rob: It makes me laugh.

Jenny: The funny thing is I’ve honed this thing over three or four years of living in the same apartment, so I’ll be watching TV and I’m like, “Oh, that book needs to move one slot to the left.” What you see, it’s like my bonsai tree. I just get to prune at it every single day. What you don’t see is the back of this Ikea shelf is all the reject books that don’t have a pretty color.

Rob: That is too funny. Jenny, I think a lot of our listeners may not know who you are, have seen your work. You’ve got a fantastic book that we definitely want to talk about, but maybe you could start by just telling us a little bit about your story.

Jenny: The best place I like to start is that I felt like I was losing my mind every few years, that I worked at a startup for two years, I took a leave of absence from school. Then I moved over to Google. The career conversation I regret the most is the one I never had, and it was to tell the founder at the startup that I was getting bored and, I didn’t have the language for it at the time, but hitting a plateau or a pivot point. I moved over to Google, and I was at Google five-and-a-half years doing AdWords, began then later coaching and career development. Half way through my time there, I wanted to leave.

I certainly thought something was wrong with me, like, “If I can’t be happy at Google, I’ll never be happy anywhere. I must be one of those entitled millennials that the media keeps talking about.” But at the same time, while I was there I trained over 1,000 people. I was there as the company grew from 6,000 to 36,000. I saw how many people were struggling with this question of what’s next. I started a blog, the Life After College website, in 2005. That’s ancient in internet dog years at this point. That was my side hustle that, in 2011 when my first book was coming out, I decided to do an unpaid leave, go do a book tour, self-funded book tour, and ultimately made the choice not to go back to Google.

I thought there again, “Okay, this is the hardest career decision I’m going to have to make, but I’ve got to try. I’ll forever regret not going all-in and giving my own business a chance.” And, as you mentioned in the intro, I was burning out. I was doing too much. Google is really intense all day, all week, and then my blog and book on nights and weekends. Then, sure enough, two years into running my own business, once again I was wondering what’s next. I had become known on podcasts as the girl who left things, the girl who left college, the girl who left Google. I felt like I couldn’t escape. Even when I was at Google, when I would tell people I worked there, it was, “What’s it like? What’s the culture like? Can you submit my résumé?” Then, as soon as I left, on all these podcasts, “What was Google like? Talk to us about Google.”

I felt like, “Who am I? What is next for me? What am I moving toward, not just away from? What can I create a movement around? How can I create a bigger impact?” As I wrestled with those questions, I paused most of my business activities. I was having a personal apocalypse year. I don’t know if either of you have had one of those, where everything that can go wrong will, starting with a breakup pretty much on January 1st.

Kira: Oh, man.

Jenny: Yeah. Now my business bank account dwindled all the way down to zero, to the point where, as recently as 2014, January, I didn’t know how I was going to pay the rent in two weeks. At that point, the question isn’t the lofty, “What would you do if you knew you wouldn’t fail?” but, “What do you do when your back is up against the wall?” I had to figure this out. Otherwise, I was going to have to fold my business or move out of New York, and neither of which I wanted to do.

The last few years now have been dedicated to exploring, how do we get better at answering this question, “What’s next?” How do we be more resilient in the face of change? What is this movement that’s happening where … As I mentioned, I thought I was the only one. I thought I was going crazy and I was destined to never be happy. As I started researching Pivot, I found that everyone’s going through this more often. We’re not just granted two times in our life a mid-life crisis and a quarter-life crisis in order to search this existential questioning of who we are and what’s most important. We’re all, especially anybody listening to a podcast like yours, questioning, “Am I learning and growing?” every few years we’re going to be cycling through those questions.

As I worked on the book, I adopted the motto, “If change is the only constant, let’s get better at it,” and that’s been my focus, is helping us all accept career change as normal, not beat ourselves up over it, and have a process to move through it more easily, whether we’re self-employed or we work for someone else or a combination of both. I’m happy to say that now I’ve been running my business over six years, and in the first four months of this year I’ve earned more than the last three years combined. The things that I’ve been studying and talking about are working.

Kira: Wow.

Jenny: I feel much calmer, even though I still have no clue what’s next, really. I feel so much calmer going through the process.

Kira: Wow. There’s a lot we want to dig into here. If we could back up, before Pivot, when you just started your own business and you had left Google, how did you start your own business? What did you do to get it going and to rev up the engine in those early days? I’d also love to hear about what wasn’t working, because you mentioned that your bank account dwindled down. Something was working and something wasn’t working. I’m sure that would be relevant to the new copywriters who are just launching their businesses.

Jenny: Well, that’s very Pivoty of you as well, because Pivot is all about focusing on what is working. The biggest mistake I made when I was running my own business was focusing so much on what I didn’t want, what I didn’t know, what I didn’t have. It’s very easy when we’re self-employed to have that fear of, “I don’t want to go broke. Okay, well, I don’t want these nightmare clients. Okay, well, I don’t want this.” None of that moves it forward. It wasn’t until I started to look at what was working. How did I already get clients? What kind of clients did I like the best? What was already bringing in income, like my book, my speaking engagements? Even if I didn’t want to talk about life after college for the rest of my life, I had activities that were working, and now I just needed to shift to them.

There’s the idea of a pivot as well, that it’s not a 180. It’s not like I quit Google to become a full-time yoga teacher, which, I had gone to teacher training, so maybe that wouldn’t have been out of the question, but I was doing coaching and career development at Google, and I left to do coaching and career development on my own.

You asked about getting momentum in those early days. I blogged, and I think now blogging is not the most direct way. If anything, it’s podcasting where more people are hanging out. Less people I find … I think we’re so over-saturated on the information front. But starting to add value. I shared a lot of free templates on my site in the early days that people passed around. I still have over 30, maybe like 50 now, free templates at if you just go /toolkit. People really gravitated toward those and shared those.

Then I learned over time how to be vulnerable. I used to think that if I’m vulnerable in my writing publicly, nobody is going to want to hire me as their coach. I found the exact opposite to be true, that the more vulnerable posts I would write, the more people would inquire and want to work with me, and the more I told my story. Then it was doing things in my life that people found compelling. When I left Google or when I went to go work and live in Bali for a month, I thought, “No one’s going to want to work me. They’re going to think that I’m not focused or not there for them,” and those were the times I got the most clients in the history of my business.

I think the other mistake that I see a lot of new businesses make that I made is it’s really tricky if you’re only doing project-based billing. This is getting into nitty gritty, but especially for writers, freelancers, coaches, when I was charging by the project, it was really hard to know who was paying me when, and where the rent money was coming from. One of the biggest shifts I made that was such a game changer was moving to a monthly retainer, where I would bill people on the first of every month. Even for copywriters, you could think about, even if it’s a retainer of how many hours a month a client is getting and you estimate it out.

I would say that those retainers, they’re good until canceled, because I wanted to set the expectation that just because this one project or this one transition is done doesn’t mean we have to stop working together. Every month we can pick another thing on your plate and strategize around that. Especially for copywriters, it’s a shift, but what if you were to go on a retainer, even if it’s a ghostwriting book writing project? But when that’s done, you ask, “Okay, what’s next? You need to write articles to promote that book or spruce up your social media profiles.” You can be proactively pitching how to fill that month or work with your clients.

But what I loved about that was I could now get 5 or 10 clients on a monthly retainer and know exactly how much I was earning every month, and that really helped stabilize. I call it in the book the cashflow cow, where I really knew that my baseline was taken care of every month and I wasn’t panicked about trying to chase down big paychecks.

Rob: Jenny, you mentioned that you moved from one related thing to another, and I think that’s a really big point that you make in your book. Can we talk about the Pivot Method? The starting point is, how do you actually make a pivot? What are the steps that you would want to go through in order to shift from what you’re doing now or what you were doing then to what you want to do next?

Jenny: Sure, yeah. The analogy that came to me that was really helpful is that of a basketball player. I describe this in the book, that when a basketball player stops dribbling, one foot stays firmly planted. That’s their plant foot. It’s their foundation and their source of strength and stability. Then the pivot foot can look for passing options around the court. When someone is at a pivot point … By the way, not all pivots have to be huge and dramatic, like quitting your job. Anybody listening can do pivots, use this method as, “How do I want to grow in the next year?” or, “Where do I want to take my business? Where do I want to take this project?” This process is a way to just map growth. It doesn’t have to be always such a dramatic change.

In order to do that and to grow from your source of strength, the first stage is plant, and that’s what is working best right now, what is already working. What are your strengths, your values, your ninja super powers that people come to you for advice on most often? Another critical part of the plant stage is, what does success look like a year from now? That, even if you don’t know the specifics of how you’re going to get there — in fact, you shouldn’t know at this point or worry about it — how do you want to feel on a day-to-day basis? How much do you want to be earning in your business or your side hustle? What types of clients would you love to be working with? What kind of impact do you want to make? What else would be happening in your life or business that would just have you jumping out of bed with glee every day? If someone wrote you a glowing thank-you note or you got an award or a big media site profile, what would it be about?

Starting to craft that vision of, what would be really exciting? And just one year from now, because I believe that too much farther out and none of us can predict the future. That’s why the subtitle of the book is The Only Move That Matters is Your Next One. Don’t worry about the five-year plan.

Once you have where you are now, where you want to end up generally, that’s your plant stage. Those are your brackets for your pivot. Now, the second stage, scan, can be so much more efficient and effective because it ties into your strengths and where you want to end up. Scanning is about people, skills, and projects that are related to your strengths and your one-year vision that are compelling.

People. Who is doing what you want to do? Who do you admire? Who might you be able to reach out to? Who are some frientors that you could partner with? I love that you two are doing this podcast together, that, Kira and Rob, you thought, “Okay, hey, here’s a person I would love to work with and collaborate with.” By the way, then, people: Bringing people onto your podcast is another way to make those connections.

Skills. How do you want to grow? In order to get to that one-year vision, what skills do you need? How do you want to learn? Even personal classes that might be fun to take. Even pursuing skills or curiosities that seem like they have nothing to do with your business. What would be energizing to pursue?

Then, the third stage is where it gets fun. It’s called pilot. This is like passing the ball around the court. Piloting is about running small experiments. It’s about taking the pressure off of having the answer and actually removing all expectation to have the answer and instead running a series of small experiments that help you test what I call the three Es: Do I enjoy this new area? Can I become an expert at it? Is there room to expand in the market?

For somebody, maybe someone listening, maybe one of you thinks, “You know what? That monthly retainer thing sounds good.” Well, great. Before you tell all your clients you’re shifting, why don’t you set up your one next client on a monthly retainer? That would be a pilot. It’s a small experiment to see, “Do I even like this? Does this work?” That way, you don’t panic yourself by thinking that you need to flip your whole business over all at once. Even taking on another type of copywriting project than you might be used to, that would be a pilot. Changing the way that you work, that would be a pilot. Experimenting with your client onboarding process, that could be a pilot. There are so many small things that you can do that, again, the more that they tie into what you come up with in the plant and scan stage, the better. You can repeat that cycle — plant, scan, pilot — over and over and over and be perfectly happy.

Then the fourth stage, launch, is every now and then there’s a bigger pull-the-trigger moment, like for me quitting Google, for someone else maybe finally hitting publish — excuse me — on their website or sending an email to friends and family like, “Hey, I’m open for business. Send me your clients.” The launch moments are exciting, but they’re no longer a leap in the dark that it might be without following this process.

Kira: Jenny, how can we approach this with the right mindset? Because I think you’ve alluded to this already, but there’s some strange emotions around Pivot for me personally, because I feel like when I am pivoting or thinking of what I want to do next, I almost feel guilty because it makes me feel like I’m distracted or unfocused and I don’t know what I want, when I know pivoting is good, and you’ve proved that, but I feel like I need the right mindset to go into it and make it work, and there’s a lot of fear. How do I deal with that?

Jenny: I’m so glad you brought up the fear and the inner dialogue that we often have with ourselves. I know when I was thinking of leaving Google, I have this raging inner CFO that was like, “You’re out of your mind. You’re totally messing this up. You have a great salary, bonuses, three meals a day.” Oddly enough, my mom had the exact personification of this inner voice that I had, so my mom was then saying to me in the real world all of the things I was afraid of.

What’s so funny is I went ahead and I wrote a business plan for myself and for my inner CFO. I really didn’t plan to show it anybody but my inner CFO. That gave me the confidence to say, “Okay, Mom, I know that this isn’t what you would do, but I’m going to do this anyway, and just give me a chance.”

What’s funny is that when I was going to edit the book, this is five years later, and I wanted to put in a little tidbit about how, well, now that my mom has seen me generally successful, it’s been five years, now, has she come around? I was going to tell this nice story in the book of how she just came around, and my mom’s like, she was like, “No, I still don’t agree. I still don’t agree with when and how you left Google.”

I just had to give this little tangent that sometimes we have inner fears, sometimes it’s people we love that are afraid for us, and they’re not always going to be onboard, that our family wants to keep us safe and well-fed, and so does our inner CFO. But we often have values around freedom and growth and impact. It’s about reconciling the two.

In your case, Kira, I would say it’s reframing, because I know what you mean, and career change in particular can be very scary because it seems to threaten our livelihood, our ability to provide for ourselves and our families. That’s where really small next steps can be helpful, because we just show ourselves, like, “Oh, hey, this little thing is working. Let me pour a little more juice and attention into it. Okay. Oh, that’s working again. Let me keep going.” It’s very incremental.

It’s also looking at, what’s more important than the fear? Yes, I’m afraid. Yeah, I feel a little uncommitted if I’m looking in a new direction, but what’s more important to me than that is growing my business or is expanding my reach, is making a bigger impact. That has always helped me.

Then the last thing I’ll say is that I do not expect my fear to go away. There’s a lot of really masculine language in our culture around, “Smash your fear, destroy your fear, crush your fear, annihilate your fear.” That never worked for me. I’ve lately … I want to write actually a little short book on this. There’s even talk of slaying dragons, your fear dragons. I call it domesticating dragons, that it’s like, “Hey, dragon. How are you? Thanks for coming.” Our fear just wants to keep us safe. It’s just trying to protect us. If you have a dialogue, like, “Okay, what are you afraid of? Cool. Have a seat.” We’re going to keep going, but there’s no need for it to go away.

That took a lot of the personal beating myself up away, because, I don’t know, maybe for some business people or authors they don’t have as much fear and insecurity and uncertainty, but I certainly did. The only thing that’s had to go down is not expecting it to go away. Now when those things show up, I take it as a good sign, I’m on the right track, I must be stretching myself, and keep going.

Rob: Jenny, when I look back at my career, I can see different times when I knew that I should be thinking about making a change. I was unhappy. Or, others may be thinking, “I’ve just lost a job, so it’s obvious I need to do something.” But what about when we hit plateaus and maybe we’re in the situation where we ought to be starting to think about that next change or the pivot, but we maybe don’t see it because we’re stuck in that plateau? How can we identify those kinds of times so that we can always be pivoting to whatever is going to be better for us next?

Jenny: Just as you said, it’s an inner feeling. The plateau often starts as a whisper, just a tiny whisper, like, “Psst, I think there’s more out there for you.” If we don’t pay attention, it starts to get increasingly more uncomfortable. Sometimes our bodies start making the case for change or we get sick more often or headaches or we just cannot bring ourselves to do a certain task. Sometimes that’s a sign that we just need rest. It’s not that, “Oh, we need to pivot dramatically,” but maybe it’s just taking a step back and giving ourselves permission to rest and recalibrate. Then, at other times it’s, okay, just even acknowledging, “I am at a pivot point,” or, “I’m at a plateau,” that can be empowering to just notice it without having to fix it.

Then what I find helpful is, when I start to feel a plateau, I ask myself … One of my mottoes while writing the book was, “Let it be easy, let it be fun.” If I’m hitting a wall with something, how can I shift this to let it be easy, let it be fun? Maybe you change the way you’re working. In some cases, it might just mean that you need to raise your rates so that you don’t resent the work and it actually feels exciting and worth it. Maybe it’s changing the type of client. There’s also something that would help lighten things up. I think it’s nice to ask those questions of what that would be.

I also like to go through “do, drop, or delegate”. Of everything on my plate, especially when I’m at a plateau or I just really need to make a change, what do I know that I want to do for sure? What can I drop altogether? Then, what can I delegate? How can I bring on help to do work that … I believe in doing work that only I can do and then really constantly trying to ask, how can I delegate the rest?

Kira: I love that, “do, drop, or delegate.” I definitely need to do that.

Rob: Drop and delegate especially, right?

Kira: Yeah, right. I’ve got “do” down. I want to hear more about your pivots, because you’ve had many pivots, and I’m really thinking about you shared that in the first few months of this year you made more than you had in the previous years in your business. What was the pivot you made to go from that moment when you weren’t sure if you could pay your rent to this thriving business that you currently have?

Jenny: I gave two webinars on this that … If anyone wants to join, I have a private community called Momentum. I’m really not trying to be this pitchy about it, but these webinars are in there. They’re both an hour. I talked about multiple streams of solopreneur income, that really the first five years of my business was about developing multiple streams of income. The problem was that I was still the bottleneck. For five years, if I got sick, if I was traveling, if I needed time off just for emotional apocalypse year reasons, the business ground to a halt. I was the only one that could do the coaching. I was the only one that could do the speaking.

The next webinar that I did this year is called Scalable Streams of Solopreneur Income. My big goal, in tandem while writing Pivot … I worked on Pivot for three years, and probably for the latter two years I spent equal attention to building scalable streams of income at the same time while writing the book so that when the book came out I would not make the same mistake that I did with my first one. That mistake was that when Life After College came out, I was the only person they could hire, and I really didn’t have much else for people to do, other than hire me. When Pivot came out, I had corporate speaking and workshops. Google ended up licensing Pivot as global career development training, so we are still working together to this day. That surprised me. Came out of complete left field.

Kira: Wow.

Jenny: But it’s a testament to Pivot continuing. Google and I continue to run in parallel, which is pretty amazing.

Then I did … Kira, we both worked with Actionable Conversations. I created an actionable what I call a workshop in a box that companies can run without me. Then, on the side for individuals, I created Momentum, this private community for side hustlers and solopreneurs where I do calls twice a month, Q&A calls, and then they get access to my full course library and a private Facebook group.

Momentum was the way that, okay, if someone finishes the book and they want to keep in touch, they can join Momentum. It’s now $125 a quarter, so it’s not for what everybody’s getting. Like I’m doing an eight-week delegation ninja course coming up. It’s free for people who are in that. I try and throw in the kitchen sink, because, this is another solopreneur tip, I hated launching products. I hated writing sales copy. I probably need someone who’s listening to this podcast to come help out. I wanted to only ever sell one thing, and that was Momentum. I didn’t want to keep having to go through the whole rigmarole of launching course after course after course. That model of an online business just didn’t work for me.

Then, finally, the last scalable thing that I did was training six Pivot coaches, so while I’m on the road speaking and I have very little time to take on regular clients, these six Pivot coaches are amazing, some of my favorite people, and people can hire and work with them for a two-session jump start.

All of those things I just described, I was very strategic about building them before the book came out. But at the same time, I had no clue which of them were going to work or take off. I have pilots that didn’t go anywhere. Even I mentioned Actionable Conversations, the workshop in a box, I thought companies would be snapping this thing up. I thought they were going to be, like couldn’t wait to go facilitate Pivot on their own, and have yet to have someone really implement that in a material way, whereas the Google thing came out of nowhere.

That’s what I mean about pilots. I think of them now, to switch metaphors, as race horses at the Kentucky Derby. Your job is just to line up all these different sources of income, and ideally some scalable, even if not everything is, and then lift the starting gates and see which ones take off.

Kira: I love thinking about this scalable streams of income and that, yes, you did have multiple streams of income, but you were the bottleneck. I think that happens to a lot of copywriters. Most of us start off working on client projects, and there’s a lot of burnout involved. I think many of us struggle to create scalable streams of income, but it is possible for copywriters. Do you have any advice or maybe a baby step or two to help copywriters think a little bit bigger and think about their business in terms of scalable streams of income, or even something they can do if they want to move in that direction they can do this month to get started?

Jenny: Yeah. The first relief valve that I ever experienced in my business … This is very funny, but I was dating a guy for about a month. Then I got a breakup and a job offer in the same email.

Rob: Wow.

Kira: What?

Jenny: Yeah. Because I couldn’t help but, while we were going on dates, he was starting a business, and I was like, “Oh, don’t hire a web designer for 15 grand. Just use Squarespace. Oh, maybe don’t do that, do this.” I was constantly throwing out tips. I couldn’t resist. I knew maybe it wasn’t the feminine thing to do, I was going to put myself in the friend zone, which, sure enough, I put myself in the friend/business zone, for a combination of other reasons that don’t have to do with that. But, bottom line, I couldn’t help but … I was so interested in his business and what he was doing and giving all these tips.

When he sent that email, it was like, “Hey, do you want to manage our social media for … You’re so good at this stuff. Do you want to manage our social media?” What I did was pitched them a role they didn’t even know they needed. I said, “Yes, but what you really need is a director of operations.” I created a three-page proposal of my role, what it would include. It included social media, but it was much more strategic. It was, “I will help you set a strategy for community building, marketing, social media, outreach, grant writing, all the things.”

This was for a hydroponic urban farming company, so growing basil out of two shipping containers in Red Hook, Brooklyn. I didn’t know the first thing about growing basil, but I did know how to set up all the technical systems that they didn’t, and these are two guys who were former Wall Street traders. They’re in the book. We had a call. By the way, they wanted to pay me $1,500 a month, and I said, “$3,000 a month, and I’m already giving you a bargain, because my one-on-one coaching … “ They were getting a good deal compared to my other rates. I pitched the role, I doubled the price, and they accepted.

Then, what’s more interesting and where I think copywriters can experiment, is I hired my assistant, Marisol, to deliver 80% of what the guys were hiring me for. I set the strategy, and I delegated much of the work to her. I had Marisol writing the tweets, drafting social media strategy, implementing that strategy, but I was still providing the strategic direction and I was double-checking and looking over everything. If you’re going to sub-contract, either the client doesn’t need to know, or they can. In my case, I told the guys, “I work with Marisol on a lot of this stuff.” They didn’t need to know what the breakdown, the ratio was. That was the first thing that allowed me to earn a chunk of income and not be the one doing all the work.

I would encourage all of you listening to look at, “If I were to hire someone,” what are the aspects that you can delegate, even if it’s things like client onboarding, invoicing, social media strategy? It doesn’t mean that you’re not still going to oversee it, approve it, edit it, and do things like that, but how can you give yourself some breathing room?

Even before you think about who to hire and how to delegate to them, one thing I really recommend in terms of delegation and scaling yourself is start to track all the things that you do when you work with a client, because when you think about it in an abstract way, it might be like, “Oh my God, there’s nothing. I can’t let go of anything.” But when you really look at what tasks are involved over the course of a month or several months or a whole project, there’s more than you think.

Once you start delegating small easy stuff, then you can take bigger risks with what … I don’t know about you, Kira and Rob, but, oh man, do I have to pry my little perfectionist fingers off of so many things in my business that it’s not easy to want to delegate things, but I’ve just learned that it’s the best way forward.

Rob: I totally agree with that. In fact, that’s why I haven’t delegated, because every time you rely on other people, you think, “Are they doing it as well as I would do it?” But you’re right, if they can do it even half as well but at a significantly lower cost or they can help you do something different that’s more interesting or more profitable, I definitely need to take that advice a lot more.

Jenny: Yeah, and not to underestimate the power of delegating personal stuff. I work with a company called She Can Coterie, and I’ve worked with them for years. I delegate everything from buying plane tickets, researching things, buying purchases online, disputing things on my credit card statement, or renegotiating a phone bill. I hire a cleaning person to come once every three weeks. There is so much that I do, that it’s just that those are all things I don’t need to do. Maybe if someone is not yet ready to let go of very important client work, maybe there’s other stuff in life that you can take off of your plate so that it at least frees up all those tiny tedious tasks that you don’t have to be the one to do.

When I talk to people, they’re often intimated, like, “Well, I can’t afford that.” My first VA, I started out paying $200 a month. I was broke. I was going broke, and that was the last thing. I would rather eat PowerBars for dinner than give up my VA for how much she was crucial to my life and business. Everybody’s different, but it doesn’t have to break the bank in order to get going in this direction.

Rob: All right. I’ve got work to do there.

Kira: I was going to interrupt before Rob asked a question just to ask, what was the website you used for the personal tasks?

Jenny: Oh, yeah. It’s called I’m going to be sharing … It’s just fun. I’m building this delegation ninja course right now, so I’ll have to get you guys in there. We can give a discount to everybody listening. We can put that in the show notes. I’m happy to give you guys a special offer if any of you want to join.

Rob: Awesome. We will definitely promote that. In fact, I want to talk a little bit more about your thinking around systems, but before we do that, one of the things that strikes me, Jenny, that you’ve done really well throughout your career, starting with Life After College and that book and then what you’ve done with Pivot and what you’ve done with your own community, is that you’ve built a killer platform that you can now build anything on top of. I think that’s something that a lot of our listeners would love to know more about.

What are the things that people can do to build their own platform for finding clients or for creating products, just getting attention and getting out there? Do you have some suggestions, things that we could be doing?

Jenny: Even if you don’t call it blogging, I think one of the most effective things, I refer to it as public original thinking. Being original and figuring out how you can carve out a niche as an expert is I think important. My friend, Dorie Clark, is the pro at this. Her book is Stand Out. It’s five different methods to establish yourself as an expert. One of them is curating interviews, just like you’re doing here. Her next book comes out in October. It’s called Monetize. I actually can’t wait. I think it’s such an important complement to, first you stand out and you learn how to build a breakthrough idea, then you learn how to monetize it.

But Dorie is really good at blogging publicly. When I say that, meaning she writes for sites like Harvard Business Review, and she has grown her list tremendously. She’s so much better at it than I am, because I don’t ever really care what my numbers are. Dorie writes for sites like HBR, and then she gets her exact target clients now signing up for her newsletter and part of her ecosystem, and they’re the ones hiring her to speak and signing up for her courses. I think having a personal blog has actually gone away a little bit in favor of blogging on bigger platform sites that already have an audience like HBR or Fast Company or Forbes, Huffington Post, even re-posting your stuff on Medium.

Then, original and vulnerable. Copywriting is a good example. So is coaching. There are a ton of coaches out there. Being vulnerable and telling your true, real story, that’s what’s going to attract people more than just saying, “I’m the best copywriter out there,” because they want to build some connection. Being original, part of that is the niche of, who do you love to work with? I read a book called Book Yourself Solid when I was first starting out, by Michael Port, and it’s all about finding your red carpet clients and how you’re going to provide them red carpet services. Who do you love working with? Be specific. Don’t be afraid to be specific.

I would post language on my site, in the beginning it was just like, “I like working with young professionals. Sign up here. I’ll help you feel more fulfilled.” Okay. Then, later, for example when I was launching Momentum, I would write things like, “Are you smart, generous, creative, engaging, positive?” I put all these adjectives of the people that-

Rob: Yes. Yes I am.

Jenny: Great. Well, come on in. I was like, “You know what? I don’t want someone here if they don’t self-identify as generous,” and I wasn’t afraid to put that in the copy describing who’s going to be the best fit. I’m just saying that now because even though it’s not directly platform building, I do think that what it means is that, even if you have a smaller platform, they’re more exactly who you want listening and in your sphere.

The other thing I strive to do is be helpful. When I write my weekly newsletter, I’m always sharing one thing I’m reading, something I’m watching, and a tool or two that I’ve found around the web. I want people to, even if they’re filtering all their newsletters to some other folder, which I know so many of us are doing now these days, I want them, when they see mine, to go, like, “I always learn something new in that one, so I’m going to read it.” My friend, David Moldawer, I don’t know if either of you know him. He’s a great writing coach and editor. His newsletters are hilarious. They’re so funny and they’re so smart. His edge is not that he’s providing the latest app that you need to use, like I would do. His is just so funny. It’s like I can’t wait to read his newsletter while I’m working.

I think, think about, this goes back to the Pivot Method, what are your strengths as a writer and a person? What are your quirks? How can you include them all and not think that you have to just put on one face for your business and another one in your personal life? I’ve had the most success when I blend those things.

Then, actually let me just … I know I’m … I have so much to say on all these topics. The last thing I’ll add is…

Kira: Keep going.

Rob: Yeah, keep going.

Jenny: Okay.

Rob: We’re going to book you for episode two in the next hour.

Jenny: Thank you. It’s like, sorry to … You got me going on all the things that I really learned the hard way over the last 10 years. I learned that as a small business, I really did not like selling small things to many people. That is the online marketer model, is, “Let me sell small courses to as many people as I can, and I’m going to build a Marie Forleo sized business, even though her course is $2,000.” It didn’t work for me. I tried it over and over. I really did, and it never worked. I always dreaded my to-do lists around those kinds of things.

What I started to do was offer a ton of value to my community for free. Momentum is really low investment for what I throw in there and offer to that. Beyond that, my platform is everyone in my community, they’re welcome to come hang out, but I stopped expecting things and being disappointed when I would launch things and they wouldn’t sell as well as I wanted. Instead, I shifted to, how can I land corporate clients that fund the rest?

The thing that took the pressure off of platform building and then trying to squeeze a living out of my platform was, and I had a friend say this to me, “JV, you need to be a line item in somebody’s budget.” Instead of coaching solopreneurs on their last pennies, which I was doing for a period — and it’s rewarding but a lot of pressure for both of us — if Google hires me or if companies hire me … Think about, for all of you running a copywriting business, what would it look like to have one client at 10 grand a month, one business or two clients at five grand a month, so that no matter what you’re doing on platform side, your bills are paid?

Often, getting those clients is a little different. Yes, it involves public original thinking and posting, but it’s often going to come from your network, from being proactive about pitching projects, and things like that. That’s the last thing I’ll say on the platform.

Kira: No, I agree 100%. I think that’s the stage I’m in now as well. It’s just a couple of clients, it’s dependable, but it gives me the freedom to grow a platform and to focus time elsewhere. But it takes a while to get there. It takes a lot of work to get to that point, but it is possible.

I want to pivot, Jenny, and ask you about burnout. I’d like to hear about what happened after you launched your book. I have never launched a book, so I can only imagine how tiring and challenging it is, also exciting. What did you do after the launch was over? How do you figure out where to go after something as big as that?

Jenny: Yeah. I was surprised. I call it the void. Once you launch a big project, sometimes there’s this void that opens up, this “what’s next?” limbo where you are truly in between. I thought that was going to come. I knew I would be tired. After launching the book I did a big two-week travel promotion push, did a ton of podcasts in the months leading up. I had no idea how much rest I was really going to need. It consumed me. I did what I could, and then I thought I would rest for a week, maybe two, maximum a month. The book launched in September. By January, I did a silent meditation retreat. Came home, was like, “Okay, time to get to work. It’s the new year.” Still didn’t want to do anything. I was doing the minimum. I was keeping up with clients and going to speaking engagements. I could not bring myself to do much of anything else.

In fact, I had to write the afterward that’s going to come out with the paperback edition of Pivot in September. I had six months to think about this thing. It was due March 1st. I still had to ask for an extension. Then April came, and I struggled with that thing every day. Every day was a struggle just to write a four-page afterward. I don’t know how I wrote the whole book, because I just didn’t have any mojo. The writing mojo just wasn’t back yet. It’s been a journey of giving myself time to just … I don’t know. I couldn’t believe just the effort that when into it, and then how little of that mojo I have on the other side for writing. I’m creating the delegation course, but thankfully that’s so different than writing a book or even an article. I’m just letting that be okay for now. I do like talking about it to let people know this does happen, and I think it’s a natural part of the creative process.

Then the other post-launch thing that’s been really interesting is just all these pilots that I’ve described. For three years I was the woman writing a book called Pivot, and once it launched it was this weird feeling of, like, well, who am I now? Yes, I wrote a book called Pivot, but I’m still facing the question, what’s next? People are already asking, “Well, what’s your next book?” Someone told me at a party, they’re like, “You know, the sweet spot is two years between books.” I’m like, “What?”

Kira: Yeah.

Jenny: I know. I’m like, “I can’t force myself.” There’s no way I can start on something right now, period. I’m just letting these business pilots, I’m observing them. I have fun with them. That’s actually the thing I love, and the speaking. I pilot with my rates. I’m experimenting. That’s where I’m at now, and then just letting creative ideas incubate, but taking the pressure off to do anything about them.

Rob: Jenny, we are starting to run out of time, but I want to ask about how you went about even creating the Pivot Method. Did that come out of your coaching or was it really by sitting down and writing the book and going through it specifically? If I wanted to do something similar or if another writer wanted to do something similar, what kind of steps would we want to think through the things that we know in order to create that?

Jenny: Yeah, it is a combination of the 10 years of coaching that I’ve done, career coaching and studying careers, and my own personal experience, my own struggles. I think so much of IP can come from, what have been your biggest challenges and how did you overcome them? Because when you are the one in the trenches, you have a front-row seat to how to solve it, whereas someone else who was maybe more resilient in their career and about asking and figuring out what’s next, or who maybe just doesn’t make a lot of changes at all, they wouldn’t even have the impetus to write this book because it’s not on their radar as a challenge, whereas for me I felt like the sky was falling every two years, and so I’m like, “Ah, I have to fix this.”

My strength is in systems and organization and creating order from chaos, so it worked for me to create a method for a messy thing called change. That’s in my line of what I like to do. I would recommend thinking about what your unique challenges are, how you’ve uniquely solved them, how your brain works. Dorie’s Stand Out book would be great, because maybe you want to curate a book, like Daily Rituals by Mason Currey. He researched all these great writers and what their morning rituals were. Or maybe you want to come up with a method, like I did, a pivot method or some method or thing, a process. Dorie gives the example of the stages of grief. Maybe you’re doing original research. It really has to hook into your strengths.

Then, yeah, it’s I think testing it and seeing, “Does this work?” so that by the time you are writing about it, you have examples and you know that it’s road tested and you have the confidence to then say, “This thing works. I’ve tried it,” or, if you’re curating interviews, developing that unique flavor of what it is that you offer.

I would say to start with those things, and if you really are interested in building expertise, the Stand Out book is a great place to start.

Kira: Jenny, this has been an incredible hour. I feel like there’s so much in here, and if anything it’s so nice just to know we’re not the only one. It’s good to know that other people are feeling the same way and dealing with the same challenges and forced to pivot as well. Thank you for your time. Let us know where we can find you online.

Jenny: Sure. Thank you so much for having me. It’s so fun. Thanks for letting me jam about all this stuff. Really excited to be here. I love what the two of you are up to. Thank you, and big thanks to everybody for listening. If you want more, there’s a ton of free resources at I would invite anyone who’s interested, I do Q&A calls every two weeks in Momentum, and then delegation ninja is coming right up, so I’ll send you guys a link and a discount code if anyone’s interested in that.

Rob: That’s awesome. Let me just jump in and say Jenny’s book is incredible. I think that anybody who is working with clients or working on projects, writers, would benefit immensely, even if you’re not going through a career change, just because it helps you think through the process of how do you identify what’s next or what the possibilities are. I cannot recommend it highly enough. We’ll link to it in the show notes. Definitely it’s a book worth reading. It’s awesome.

Jenny: Thank you so much, Rob. Thank you.

Rob: Thanks, Jenny.

Kira: Thanks, Jenny.





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