267: Handling Consulting Bussinesses and Client Loads

00:36 - Panelist Consulting Experience and Backgrounds

• Debugging Your Brain by Casey Watts
• Happy and Effective

10:00 - Marketing, Charging, and Setting Prices

• Patreon
• Chelsea’s Blog
• Self-Worth by Salary

28:34 - GeePawHill Twitter Thread - Impact Consulting

• Casey’s Spreadsheet - “Matrix-Based Prioritization For Choosing a Job”
• Interdependence

38:43 - Management & Mentorship

• Detangling the Manager: Supervisor, Team Lead, Mentor
• Adrienne Maree Brown

52:15 - Explaining Value and Offerings

• The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field by Mike Michalowicz
• User Research
• SPIN Selling: Situation Problem Implication Need-payoff by Neil Rackham
  

55:08 - Ideal Clients

Reflections:

Mae: The phrase “indie”.

Casey: Having a Patreon to help inspire yourself.

Chelsea: Tallying up all of the different things that a given position contributes to in terms of a person’s needs.

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Transcript:

CHELSEA: Welcome to Greater Than Code, Episode 267. I'm Chelsea Troy, and I'm here with my co-host, Mae.

MAE: And also with us is Casey.

CASEY: Hi, I'm Casey.

And today's episode, we are our own guests. We're going to be talking to you about our experiences in consulting.

To get this one started, how about we share what got us into consulting and what we like, don't like about it, just high-level?

Chelsea, would you mind going first?

CHELSEA: Sure.

So I started in consulting, really in a full-time job. So for early in my programming career, I worked for several years for a company called Pivotal Labs and Pivotal Labs is chiefly, or was chiefly at the time, a software engineering consulting organization.

My job was to pair program with folks from client teams, various types of clients, a lot of health insurance companies. At the time, there was a restaurant loyalty app that we did some work for. We did some work for General Motors, various clients, a major airline was also a client, and I would switch projects every three to six months. During that time employed by Labs, I would work for this client, pair programming with other pivots, and also with client developers.

So that was my introduction to consulting and I think that it made the transition to consulting later, a little bit easier because I already had some consulting experience from under the Labs’ umbrella.

After I worked for Labs, I moved on to working at a product company for about 2 years and my experience at that product company burned me out on full-time programming for a little while.

So in my last couple of months at that job, I realized that I was either going to have to take some time off, or I was going to have to find an arrangement that worked better for me for work, at least for the next little while. And for that next little while, what I decided I wanted to try to do was work part-time because I was uncomfortable with the idea of taking time off from programming completely. I felt that I was too early in my career and the skill loss would be too great if I took time off completely, but I knew I needed some space and so, I quit my full-time job.

After I quit the full time—I probably should have done this before I quit the job, but I didn't—I called an organization that I had previously done some volunteer work with, with whom I discussed a job a couple of years prior, but for a couple of different reasons, it didn't work out. I said to them, “I know that you're a grant-funded organization and you rarely have the funding and capacity to bring somebody on, but just so you're aware, I like working with you. I love your product. I love the stuff that you work on. All our time working together, I've really enjoyed. So if you have an opening, I'm going to have some time available.” The director there emailed me that same day and said, “Our mobile developer put in his two weeks’ notice this morning. So if you have time this afternoon, I'd really like to talk to you,” [chuckles] and that was my first client and they were a part-time client.

I still work with them. I love working with them. I would consider them kind of my flagship client. But then from there, I started to kind of pick up more clients and it took off from there after that summer. I spent that summer generally working 3 days a week for that client and then spending 4 days a week lying face down in a park in the sun. That helped me recover a little bit from burnout.

And then after that, I consulted full-time for about 2 years and I still consult on the side of a full-time job. So that's my story.

Is anyone feeling a penchant for going next?

MAE: I can go. I've been trying to think how am I going to say this succinctly. I've had at least two jobs and several club, or organization memberships, or founding, or positions since I was 16. So wherever I go, I've always been saying, “Well, I've done it these 47 ways already [laughs] even since I was a teenager.” So I've sort of always had a consulting orientation to take a broader view and figure out ways in which we can systematize whatever it is that's happening around me.

Specifically for programming, I had been an administrator, like an executive leader, for many years. I just got tired of trying to explain what we as administrators needed and I just wanted to be able to build the things. I was already a really big Microsoft access person and anybody who just got a little [laughs] snarky in there knows I love Microsoft Access. It really allowed me to be able to offer all kinds of things to, for example, I was on the board of directors of my Kiwanis Club and I made a member directory and attendance tracker and all these things.

Anyway, when I quit my executive job and went to code school in 2014, I did it because I knew that I could build something a lot better than this crazy Access database [laughs] that I had, this very involved ETL things going on in. I had a nonprofit that I had been involved with for 15 years at that point and I had also taken a database class where I modeled this large database that I was envisioning.

So I had a bunch of things in order. I quit my full-time job and went to an income of $6,500 my first year and I hung with that flagship customer for a while and tailored my software. So I sort of have this straddling of a SaaS situation and a consulting situation. I embed into whoever I'm working with and help them in many ways. Often, people need lots of different levels of coaching, training, and skills development mixed with just a place to put things that makes sense to them.

I think that's the brief version [laughs] that I can come up with and that is how I got where I am and I've gone in and out of also having a full-time job. Before I quit that I referenced the first year I worked a full-time job plus at least 40 to a 100 hours on my software to get it ready for prime time. So a lot of, a lot of work.

CASEY: Good story. I don't think I ever heard these fuller stories from either of you, even though I know roughly the shape of your past. It's so cool to hear it. Thanks for sharing them.

All right, I'll share about me now.

So I've been a developer, a PM, and I've done a lot of design work. I've done all the roles over my time in tech. I started doing programming 10, 15 years ago, and I'm always getting burnt out everywhere I go because I care so much and we get asked to do things that seem dumb. I'm sure anyone listening can relate to this in some organization and when I say dumb, I don't use that word myself directly. I'm quoting a lot of people who would use that word, but I say either we're being asked to do things that don't make sense, aren't good ideas, or there are things that are we're being asked to do that would make sense if we knew why and it's not being communicated really well. It's poor communication. Either one, the other, or both.

So after a lot of jobs, I end up taking a 3-month sabbatical and I'm like, “Whatever, I got to go. I can't deal with caring so much anymore, and I'm not willing to care less either.”

So most recently, I took a sabbatical and I finished my book, Debugging Your Brain, which takes together psychology ideas, like cognitive behavioral therapy and programming ideas and that, I'm so proud of. If you haven't read it yet, please check it out.

Then I went back to my job and I gave them another month where I was like, “All right, look, these are things need to change for me to be happy to work here.” Nothing changed, then I left. Maybe it's changing very slowly, but too slowly for me to be happy there, or most of these past companies. [laughs]

After I left, this last sabbatical, I spent three to six months working on a board game version of my book. That's a lot of fun. And then I decided I needed more income, I needed to pay the bills, and I can totally be a tech consultant if I just deal with learning marketing and sales. That's been my… probably six months now, I've been working on the marketing in sales part, thinking a lot about it. I have a lot of support from a lot of friends.

Now I consult on ways to make teams happier and more effective and that's my company name, Happy and Effective. I found it really easy to sell workshops, like diversity, equity, and inclusion workshops to HR departments. They're pretty hungry for those kinds of workshops and it's hard to find good, effective facilitators. It's a little bit harder to get companies to pay for coaching for their employees, even though a new EM would love coaching and how to be a good leader.

Companies don't always have the budget for that set aside and I wish they would. I'm working with a lot of companies. I have a couple, but not as many as I'd like. And then the hardest, my favorite kind of client is when I get to embed with the team and really work on seeing what's going on me on the ground with them, and help understand what's going on to tell the executives what's happening and what needs to change and really make a big change. I've done that once, or twice and I'd love to do that more, but it's the hardest. So I'm thinking about easy, medium, hard difficulty of selling things to clients. I would actually make plenty of money is doing workshops, honestly, but I want the impact of embedding. That's my bigger goal is the impact.

MAE: Yeah. I basically have used my software as a Trojan horse for [laughs] offering the consulting and change management services to help them get there because that is something that people already expect to spend some money on. That, though has been a little problematic because a few years in, they start to think that the line item in the budget is only for software and then it looks very expensive to them. Whereas, if they were looking at it as a consultant gig, it's incredibly inexpensive to them.

CASEY: Yeah. It's maybe so inexpensive that it must not be a quality product that they're buying.

MAE: Yes.

CASEY: Put it that way implicitly.

MAE: Definitely, there's also that.

CASEY: When setting prices, this is a good general rule of thumb. It could be too low it looks like it'll be junk, like a dollar store purchase, or it can be too high and they just can't afford it, and then there's the middle sweet spot where it seems very valuable. They barely can afford it, but they know it'll be worth it, and that's a really good range to be in.

MAE: Yeah. Honestly, for the work that I do, it's more of a passion project. I would do it totally for free, but that doesn't work for this reason you're talking about.

CASEY: Yeah.

MAE: Like, it needs to hurt a little bit because it's definitely going to be lots and lots of my time and it's going to be some of their time and it needs to be an investment that not hurt bad [laughs] but just be noticeable as opposed to here's a Kenny’s Candy, or something.

CASEY: I found that works on another scale, on another level. I do career coaching for friends, and friends of friends, and I'm willing to career coach my friends anyway. I've always been. For 10 years, I've reviewed hundreds, thousands of resumes. I've done so many interviews. I'm down to be a career coach, but no one was taking me up on it until I started charging and now friends are coming to me to pay me money to coach them. I think on their side, it feels more equitable. They're more willing to do it now that I'm willing to take money in exchange for it. I felt really bad charging friends until I had the sliding skill. So people who make less, I charge less for, for this personal service. It's kind of weird having a personal service like that, but it works out really well. I'm so happy for so many friends that have gotten jobs they're happy with now from the support. So even charging friends, like charging them nothing means they're not going to sign up for it.

MAE: Yes, and often, there is a bias of like, “Oh, well, that's my friend.” [laughs] so they must not be a BFD.”

CASEY: Yeah. But we are all BFDs.

MAE: Exactly!

How about you Chelsea? How did you start to get to the do the pricing thing?

CHELSEA: Yeah, I think it's interesting to hear y'all's approaches to the marketing and the pricing because mine has been pretty different from that.

But before I get off on that, one thing I do want to mention around getting started with offering personal services at price is that if it seems too large a step to offer a personal service to one person for an amount of money, one thing that I have witnessed folks have success with in starting out in this vein is to set up a Patreon and then have office hours for patrons wherein they spend 2 hours on a Sunday afternoon, or something like that and anyone who is a patron is welcome to join. What often ends up happening for folks in that situation is that people who are friends of theirs support their Patreon and then the friends can show up.

So effectively, folks are paying a monthly fee for access to this office hours, which they might attend, or they might not attend. But there are two nice things about it.

The first thing about it is that you're not – from a psychological perspective, it doesn’t feel like charging your friends for your time with them. It feels more indirect than that in a way that can be helpful for folks who are very new to charging for things and uncomfortable with the idea.

The second thing is that the friends are often much more willing to pay than somebody who's new to charging is willing to charge. So the friends are putting this money into this Patreon, usually not because they're trying to get access to your office hours, but because they want to support you and one of the nice things about Patreon is that it is a monthly amount.

So having a monthly email from Patreon that's like, “Hey, you we're sending you—” it doesn't even have to be a lot. “We're sending you 40 bucks this month.” It is a helpful conditioning exercise for folks who are not used to charging because they are getting this regular monthly income and the amount is not as important as receiving the regular income, which is helpful psychological preparation for charging for things on your own, I think.

That's not the way that I did it, but I have seen people be effective that way. So there's that.

For me, marketing was something that I was very worried about having to do when I started my business. In fact, it was one of those things where my conviction, when I started my consulting business, was I do not want to have to sell my services. I will coast on what clients I can find and when it is no longer easy, I will just get a full-time job because selling traditionally conceptualized is not something that I enjoyed.

I had a head start on the marketing element of things, that is sort of the brand awareness element of things, my reputation and the reason for that is that first of all, I had consulted at Labs for several years, which meant that every client team that I had ever worked with there, the director remembered me, the product owner remember me. So a lot of people who had been clients of Labs – I didn't actually get anybody to be a client of mine who was a client of Labs, but the individuals I had worked with on those projects who had then changed jobs to go to different companies, reached out to me on some occasions. So that was one place that I got clients from.

The other place that I gotten clients from has been my blog. Before I started my business, I had already been writing a tech blog for like 4, or 5 years and my goal with the tech blog has never actually been to get clientele, or make money. My goals for the blog when I started it were to write down what I was learning so that I would remember it and then after that, it was to figure out how to communicate my ideas so that I would have an easier time communicating them in the workplace. After that, it became an external validation source so that I would no longer depend on my individual manager's opinion of me to decide how good I was at programming.

Only very recently has it changed to something like, okay, now I'm good enough at communicating and good enough at tech that I actually have something to teach anybody else. So honestly, for many years, I would see the viewership on my blog and I would be like, “Who are all these people? Why are they in my house?” Like, this is weird, but I would get some credibility from that.

CASEY: They don't expect any tea from me.

CHELSEA: Yeah. I really hope. I don't have enough to go around, [laughs] but it did help and that's where a lot of folks have kind of come from. Such that when I posted on my blog a post about how I'm going to be going indie. I've quit my job. I didn't really expect that to go anywhere, but a few people did reach out from that and I've been lucky insofar is that that has helped me sustain a client load in a way that I didn't really expect to.

There's also, I would be remiss not to mention that what I do is I sling code for money for the majority of my consulting business, at least historically and especially in the beginning was exclusively that, and there's enough of a demand to have somebody come in and write code that that helped. It also helped that as I was taking on clients, I started to niche down specifically what I wanted to work on to a specific type of client and to a specific type problem. So I quickly got to the point where I had enough of a client load that I was going to have to make a choice about which clients to accept, or I was going to have to work over time.

Now, the conventional wisdom in this circumstance is to raise your rates. Vast majority of business development resources will tell you that that's what you're supposed to do in this situation. But part of my goal in creating my consulting business had been to get out of burnout and part of the reason for the burnout was that I did not feel that the work that I was doing was contributing to a cause that made me feel good about what I was doing. It wasn't morally reprehensible, but I just didn't feel like I was contributing to a better future in the way that my self-identity sort of mandated that I did. It was making me irritable and all these kinds of things.

MAE: I had the same thing, yeah.

CHELSEA: Yeah. So it's interesting to hear that that's a common experience, but if I were to raise my rates, the companies that were still going to be able to afford me were going to be companies whose products were not morally reprehensible, but not things that coincided with what I was trying to get out of my consulting business.

So what I did instead was I said, “I'm specifically looking to work with organizations that are contributing to basic scientific research, improving access for underserved communities, and combating the effects of climate change,” and kept my rates effectively the same, but niche down the clientele to that.

That ended up being kind of how I did it. I find that rates vary from client to client in part, because of what you were talking about, Casey, wherein you have to hit the right price in order to even get clients board in certain circumstances.

CASEY: Right.

CHELSEA: I don't know a good way to guess it. My technique for this, which I don't know if this is kosher to say, but my technique for this has been whoever reached out to me, interested in bringing me on as a consultant for that organization, I ask that person to do some research and figure out what rate I'm supposed to pitch. That has helped a lot because a lot of times my expectations have been wildly off in those circumstances.

One time I had somebody say to me, this was for a custom workshop they wanted. I was like, “What should I charge?” And they were like, “I don't know, a few thousand.” I was like, “Is that $1,200? Is that $9,000? I don't know how much money that is,” and so they went back and then they came back and they were able to tell me more specifically a band. There was absolutely no way I would've hit that number accurately without that information.

CASEY: Yeah, and different clients have different numbers. You setting your price standard flat across all customers is not a good strategy either. That's why prices aren't on websites so often.

CHELSEA: Yeah. I find that it does depend a lot. There's similarly, like I said, a lot of my clients are clients who are contributing to basic scientific research are very often grant funded and grants funding is a very particular kind of funding. It can be intermittent. There has to be a skillset on the team for getting the grant funding. A lot of times, to be frank, it doesn't support the kinds of rates that somebody could charge hourly in a for-profit institution.

So for me, it was worth it to make the choice that this is who I want to work with. I know that my rate is effectively capped at this, if I'm going to do that and that was fine by me. Although, I'm lying to say it was completely fine by me. I had to take a long, hard look in the mirror, while I was still in that last full-time job, and realize that I had become a person who gauged her self-worth by the salary that she commanded more than I was comfortable with. More than I wanted to. I had to figure out how to weaken that dependency before I was really able to go off and do my own thing. That was my experience with it.

I'm curious whether y'all, well, in particular, Casey, did you find the same thing?

CASEY: The self-worth by salary?

CHELSEA: Yeah.

CASEY: I felt that over time, yeah. Like I went from private sector big tech to government and I got a pay cut and I was like, “Ugh.” It kind of hurt a little and it wasn't even as much as I was promised. Once I got through the hiring process, it was lower than that and now I'm making way less. When I do my favorite impact thing, the board game, like if I made a board game about mental health for middle schoolers, which is something I really want to do, that makes less than anything else I could with my time. I'll be lucky to make money on that at all. So it's actually inverse. My salary is inversely proportional to how much impact I can have if I'm working anyway.

So my dream is to have enough corporate clients that I can do half-time, or game impact, whatever other impact things I'm thinking about doing. I think of my impact a lot. Impact is my biggest goal, but the thing is salary hurts. If I don't have the salary and I want to live where I'm living and the lifestyle I have, I don't want to cut back on that and I don't need to, hopefully.

CHELSEA: Right.

CASEY: I'm hoping eventually, I'll have a steady stream of clients, I don't need to do the marketing and sales outreach as much and all those hours I kind of recoup. I can invest those in the impact things. I've heard people can do that. I think I'll get there.

CHELSEA: No, I think you absolutely will.

Mae, I'm curious as to your experience, because I know that you have a lot of experience with a similar calculation of determining which things are going to provide more income, which things are probably going to provide less income, and then balancing across a bunch of factors like money, but also impact, time spent, emotional drain, and all that stuff.

MAE: Well, Chelsea.

[laughter]

I am a real merry go round in this arena. So before I became a programmer, I had a state job, I was well paid, and I was pretty set. Then I was a programmer and I took huge pay cut because I quit. I became a programmer when I was 37 years old. So I already had a whole career and to start at the beginning and be parallel with 20-year-old so it's not just like my salary, but also my level and my level of impact on my – and level of the amount of people who wanted to ask me for my advice [laughs] was significantly different.

So like the ego's joking stopped and so when you mentioned the thing about identity. Doing any kind of consulting in your own deal is a major identity reorganization and having the money, the title, the clout, and the engagement. Like a couple years, I have spent largely alone and that is very different than working at a place where I have colleagues, or when I live somewhere and have roommates. But I have found signing up for lots and lots of different social justice and passion project things, and supporting nonprofits that I believe in.

So from my perspective, I'm really offering a capacity building grant out of my own pocket, my own time, and my own heart and that has been deeply rewarding and maybe not feel much about my identity around salary. Except it does make me question myself as an adult. Like these aren't the best financial decisions to be making, [chuckles] but I get enough out of having made them that it's worth it to me.

One of the things probably you were thinking of, Chelsea, we worked together a little bit on this mutual aid project that I took on when the pandemic started and I didn't get paid any dollars for that and I was working 18 hours a day on it, [chuckles] or something.

So I like to really jump in a wholeheartedly and then once I really, really do need some dollars, then I figure something else out. That is kind of how I've ebbed and flowed with it. But mostly, I've done it by reducing my personal overhead so that I'm not wigged about the money and lowering whatever my quality-of-life spending goals [chuckles] are. But that also has had to happen because I have not wanted to and I couldn't get myself to get excited about marketing of myself and my whole deal. Like I legit still don't have a website and I've been in operation now since 2014 so that's a while.

I meet people and I can demonstrate what it is and I get clients and for me, having only a few clients, there's dozens of people that work for each one. So it's more of an organization client than a bunch of individuals and I can't actually handle a ton. I was in a YCombinator thing that wanted me to really be reporting on income, growth rates, and all of these number of new acquisition things, and it just wasn't for me. Those are not my goals. I want to make sure that this nonprofit can help more people this year and that they can get more grant money because they know how many people they helped and that those people are more efficient at their job every day. So those are harder to measure. It's not quite an answer to your question, [laughs] but I took it and ran a little.

CHELSEA: No, I appreciate that. There is a software engineer and a teacher that I follow on Twitter. His name is GeePawHill. Are y'all familiar with GeePawHill?

MAE: No.

CHELSEA: And he did a thread a couple of days ago that this conversation reminds me of and I found it. Is that all right if I read like a piece of it and paraphrase part of it?

MAE: Yes, please.

CHELSEA: Okay.

So this is what he says. He says, “The weirdest thing about being a teacher for young geek minds: I am teaching them things…that their actual first jobs will most likely forbid them to do.

The young'uns I work with are actually nearly all hire-able as is, after 18 months of instruction, without any intervention from me.

The problem they're going to face when they get to The Show isn't technical, or intellectual at all. No language, or framework, or OS, or library, or algorithm is going to daunt them, not for long.

No, the problem they're going to face is how to sustain their connection to the well of geek joy, in a trade that is systematically bent on simultaneously exploiting that connection while denying it exists and refusing any and all access to it.

It is possible, to stick it out, to acquire enough space and power, to re-assert one's path to the well. Many have done it; many are doing it today.

But it is very hard.

Very hard.

Far harder than learning the Visitor pattern, or docker, or, dart, or SQL, or even Haskell.

How do you tell people you've watched “become” as they bathed in the cool clear water that, for some long time, 5 years or more, they must…navigate the horrors of extractive capitalist software development?

The best answer I have, so far, is to try and teach them how and where to find water outside of work.

It is a lousy answer.

I feel horrible giving it. But I'd feel even more horrible if I didn't tell them the truth.”

CASEY: I just saw this thread and I really liked it, too. I'm glad you found it.

MAE: Oh, yeah. I find it honestly pretty inspiring, like people generally who get involved in the kinds of consulting gigs that we three are talking about, which is a little different than just any random consulting, or any random freelancing.

CASEY: Like impact consulting, I might call that.

MAE: Yeah. It's awesome if the money comes, but it's almost irrelevant [chuckles] provided that basic needs are meant. So that's kind of been my angle. We'll see how – talk to me in 20 more years when I'm [chuckles] trying to retire and made a lot of choices that I was happy with at the time.

CASEY: This reminds me of a conversation I had with a friend who's an executive director of an orchestra in the nonprofit space and he was telling me that so many nonprofits shoot themselves in the foot by not doing enough fundraising, by not raising money, and that comes from not wanting to make money in a way because they're a nonprofit, money is not a motive, and everybody's very clear about that.

That's noble and all, but it ends up hurting them because they don't have the money to do the impactful things they would as a nonprofit. Money is a necessary evil here and a lot of people are uncomfortable with it. Including me a lot of the time. Honestly, I have to tell myself not to. What would I tell a friend? “No, charge more money.” Okay, I guess I'll tell myself to do that now. I have this conversation with myself a lot.

MAE: Yeah. I've been very aware that when I become anti-money, the well dries up. The money well. [laughs]

CASEY: Yeah.

MAE: And when I am respectful of and appreciative of money in the world, more comes my way. There is an internal dousing, I think that happens that one needs to be very careful about for sure.

CASEY: One of the techniques I use with myself and with clients is a matrix where I write out for this approach, this thing that I'm thinking about how much money will it make, how much impact will it have on this goal, and all the different heuristics I would use to make the decision, or columns and all the options arose. I put numbers in it and I might weight my columns because money is less important than impact, but it's still important. It's there. I do all this math.

In the end, the summary column with the averages roughly matches what's in my head, which is the things that are similar in my head are similar on paper, but I can see why and that's very clarifying for me. I really like being able to see it in this matrix form and being able to see that you have to focus on the money some amount. If you just did the high impact one, it wouldn't be on the top of the list. It's like, it's hard to think about so many variables at once, but seeing it helps me.

CHELSEA: It is. GeePaw speaks to that some later in the thread. He says, “You’ve got to feed your family. You’ve got to. That's not negotiable. But you don't got to forget the well. To be any good at all, you have to keep finding the well, keep reaching it, keep noticing it. Doesn't matter whether it's office hours, or after hours. Matters whether you get to it.

The thing you’ve got to watch, when you become a professional geek, isn't the newest tech, and it sure as hell isn't the org's process.

You’ve got to watch whether, or how you're getting to the well.

If you're getting to the well, in whatever way, you'll stay alive and change the world.”

I think I'm curious as to y'all's thoughts on this, but like I mentioned earlier, I have a full-time job and I also do this consulting on the side. I also teach. I teach at the Master's program in computer science at University of Chicago. I do some mentoring with an organization called Emergent Works, which trains formerly incarcerated technologists.

The work situation that I have pieced together for myself, I think manages to get me the income I need and also, the impact that I'm looking for and the ability to work with people and those kinds of things. I think my perspective at this point is that it's probably difficult, if it's realistic at all, to expect any one position to be able to meet all of those needs simultaneously. Maybe they exist, but I suspect that they're relatively few and far between and I think that we probably do ourselves a disservice by propagating this idea that what you need to do is just make yourself so supremely interview-able that everybody wants to hire you and then you get to pick the one position where you get to do that because there's only one in the entirety of tech, it's that rare.

Sure, maybe that's an individualist way to look at it. But when we step back and look more closely, or when we step back and look more broadly at that, it's like, all right, so we have to become hypercompetitive in order to be able to get the position where we can make enough while helping people. Like, the means there seem kind of cutthroat for the ends, right? [laughs]

CASEY: This reminds me of relationships, too and I think there's a lot of great parallels here. Like you shouldn't expect your partner to meet all of your needs, all of them.

MAE: I was thinking the same thing!

CASEY: Uh huh. Social, emotional, spiritual, physical, all your needs cannot possibly by one person and that is so much pressure to put on that person,

CHELSEA: Right.

CASEY: It's like not healthy.

CHELSEA: Right.

CASEY: You can choose some to prioritize over others for your partner, but you're not going to get a 100% of it and you shouldn't.

CHELSEA: Well, and I find that being a conversation fairly regularly in monogamous versus polyamorous circles as well. Like, how much is it appropriate to expect of a partner? But I think it is a valid conversation to have in those circles. But I think that even in the context of a monogamous relationship, a person has other relationships—familial relationships, friend relationships—outside of that single romantic relationship.

CASEY: Co-workers, community people, yeah.

CHELSEA: Right. But even within that monogamous context, it's most realistic and I would argue, the most healthy to not expect any one person to provide for all of your needs and rather to rely on a community. That's what we're supposed to be able to do.

CASEY: Yeah.

MAE: Interdependence, not independence.

CHELSEA: Right.

CASEY: It's more resilient in the face of catastrophe, or change in general, mild, more mild change and you want to be that kind of resilient person for yourself, too. Just like you would do a computer system, or an organization. They should be resilient, too.

MAE: Yes.

CASEY: Your relationship with your job is another one.

MAE: Totally.

CHELSEA: Right. And I think that part of the reason the burnout is so quick – like the amount of time, the median amount of time that somebody spends at a company in tech is 2.2 years.

MAE: I know, it's so weird.

CHELSEA: Very few companies in tech have a large number of lifers, for example, or something like that. There are a number of reasons for that. We don't necessarily have to get into all of them, although, we can if you want. But I think one of them is definitely that we expect to get so much out of a full-time position. Tech is prone. due to circumstances of its origin, to an amount of idealism. We are saving the world. We, as technologists, are saving the world and also, we, as technologists, can expect this salary and we, as technologists, are a family and we play ping pong, and all of these things –

[laughter]

That contribute to an unrealistic expectation of a work environment, which if that is the only place that we are getting fulfillment as programmers, then people become unsatisfied very quickly because how could an organization that's simultaneously trying to accomplish a goal, meet all of these expect for everybody? I think it's rare at best.

CASEY: I want to bring up another example of this kind of thing. Imagine you're an engineer and you have an engineering manager. What's their main job? Is it to get the organization's priorities to be done by the team, like top-down kind of thing? We do need that to happen. Or is it to mentor each individual and coach them and help them grow as an engineer? We need that somewhere, too, yeah. Or is it to make the team – like the team to come together as a team and be very effective together and to represent their needs to the org? That, too, but we don't need one person to do all three of those necessarily. If the person's not technical, you can get someone else in the company to do technical mentorship, like an architect, or just a more senior person on, or off the team somewhere else. But we put a lot of pressure on the engineering managers to do that and this applies to so many roles. That's just one I know that I can define pretty well.

There's an article that explains that pretty well. We'll put in the show notes.

MAE: Yes!

So what I am currently doing is I have a not 40 hours a week job as an engineering manager and especially when I took the gig, I was still doing all of these pandemic charity things and I'm like, “These are more important to me right now and I only have so many hours in the day. So do you need me to code at this place? I can, but do you need me to because all those hours are hours I can go code for all these other things that I'm doing,” and [laughs] it worked. I have been able to do all three of the things that you're talking about, Casey, but certainly able to defer in different places and it's made me – this whole thing of not working full-time makes you optimize in very different ways.

So I sprinkle my Slack check-ins all day, but I didn't have to work all day to be present all day. There's a lot that has been awesome. It's not for everyone, but I also have leaned heavily on technical mentorship happening from tech leads as well.

CASEY: Sounds good.

MAE: But I'm still involved. But this thing about management, especially in tech being whichever programmer seems like the most dominant programmer is probably going to be a good needs to be promoted into management. Just P.S. management is its own discipline, has its own trajectory and when I talk to hiring managers and they only care about my management experience in tech, which is 6 years, right? 8, but I have 25 years of experience in managing. So there's a preciousness of what it is that we are asking for the employees and what the employees are asking of the employer, like you were talking about Chelsea, that is very interesting. It's very privileged, and does lead a lot of people to burnout and disappointment because their ideas got so lofty.

I just want to tie this back a little bit too, something you read in that quote about – I forget the last quote, but it was something about having enough to be able to change the world and it reminded me of Adrienne Maree Brown, pleasure activism, emergent strategy, and all of her work, and largely, generations of Black women have been saying, “Yo, you’ve got to take care [chuckles] of yourself to be able to affect change.” Those people have been the most effective and powerful change makers. So definitely, if you're curious about this topic, I urge you to go listen to some brilliant Black women about it.

CASEY: We'll link that in the show notes, too.

I think a lot about engineering managers and one way that doesn't come up a lot is you can get training for engineering managers to be stronger managers and for some reason, that is not usually an option people reach for. It could happen through HR, or it could happen if you have a training budget and you're a new EM, you could use your training budget to hire coaching from someone. I'm an example. But there's a ton of people out there that offer this kind of thing. If you don't learn the leadership skills when you switch roles, if you don't take time to learn those skills that are totally learnable, you're not going to have them and it's hard to apply them. There's a lot of pressure to magically know them now that you’ve switched hats.

MAE: And how I don't understand why everyone in life doesn't have a therapist, [laughs] I don't understand why everyone in life doesn't have multiple job coaches at any time. Like why are we not sourcing more ideas and problem-solving strategies, and thinking we need to be the repository of how to handle X, Y, Z situation?

CASEY: For some reason, a lot of people I've talked to think their manager is supposed to do that for them. Their manager is supposed to be their everything; their boss. They think the boss that if they're bad, you quit your job. If they're good, you'll stay. That boss ends up being their career coach for people, unless they're a bad career coach and then you're just stuck. Because we expect it so strongly and that is an assumption I want everyone listening to question. Do you need your manager at work to be that person for you? If they are, that's great. You're very fortunate. If not, how can you find someone? Someone in the community, a friend, family member, a professional coach, there's other options, other mentors in the company. You don't have to depend on that manager who doesn't have time for you to give you that kind of support.

CHELSEA: So to that end, my thinking around management and mentorship changed about the time I hit – hmm. It was a while ago now, I don't know, maybe 6 years as a programmer, or something like that. Because before that, I was very bought into this idea that your manager is your mentor and all these types of things.

There was something that I realized. There were two things that I realized. The first one was that, for me, most of my managers were not well set up to be mentors to me and this is why. Well, the truth is I level up quickly and for many people who are managers in a tech organization, they were technologists for 3 to 5 years before they became managers. They were often early enough in their career that they didn't necessarily know what management entailed, or whether they should say no based on what they were interested in. Many managers in tech figure out what the job is and then try to find as many surreptitious ways as possible to get back into the code.

MAE: Yeah.

CHELSEA: Additionally, many of those managers feel somewhat insecure about their weakening connection to the code base of the company that they manage.

MAE: Yeah.

CHELSEA: And so it can be an emotionally fraught experience for them to be mentor to someone whose knowledge of the code base that they are no longer in makes them feel insecure. So I learned that the most effective mentors for me – well, I learned something about the most effective mentors for me and I learned something of the most effective managers for me.

I learned that the most effective managers for me either got way out ahead of me experience wise before they became managers, I mean 10 years, 15 years, 20 years, because those are not people who got promoted to management because they didn't know to say no. Those are people who got promoted to management after they got tired of writing code and they no longer staked their self-image on whether they're better coders than the people that they manage. That's very, very important.

The other type of person who was a good manager for me was somebody who had never been a software engineer and there are two reasons for that. First of all, they trended higher on raw management experience. Second of all, they were not comparing their technical skillset to my technical skillset in a competitive capacity and that made them better managers for me, honestly. It made things much, much easier.

And then in terms of mentors, I found that I had a lot more luck going outside of the organization I was working for mentors and that's again, for two reasons. The first one is that a lot of people, as they gain experience, go indie. Just a lot of people, like all kinds. Some of my sort of most trusted mentors. Avdi Grimm is somebody I've learned a lot from, indie effectively at this point. GeePawHill, like I mentioned, indie effectively at this point. Kenneth Mayer, indie effectively at this point. And these are all people who had decades of experience and the particular style of programming that I was doing very early in my career for many years. So that's the first reason.

And then the second reason is that at your job, it is in your interest to succeed at everything you try—at most jobs. And jobs will tell you it's okay to fail. Jobs will tell you it's okay to like whatever, not be good at things and to be learning. But because if I'm drawing a paycheck from an organization, I do not feel comfortable not being good at the thing that I am drawing the paycheck for.

MAE: Same.

CHELSEA: And honestly, even if they say that that's the case, when the push comes to shove and there's a deadline, they don't actually want you to be bad at things. Come on! That doesn't make any sense. But I've been able to find ambitious projects that I can contribute to not for pay and in those situations, I'm much more comfortable failing because I can be like, “You know what, if they don't like my work, they can have all their money back.”

And I work on a couple projects like that right now where I get to work with very experienced programmers on projects that are interesting and challenging, and a lot of times, I just absolutely eat dirt. My first PR doesn't work and I don't know what's wrong and the whole description is like somebody please help and I don't feel comfortable doing that on – if I had to do it at work, I would do it, but I'm not comfortable doing it.

I firmly believe that for people to accelerate their learning to their full capacity for accelerating their learning, they must place themselves in situations where they not only might fail, but it's pretty likely. Because that's what's stretching your capacity to the degree that you need to get better and that's just not a comfortable situation for somewhere that you depend on to make a living.

And that ended up being, I ended up approaching my management and my mentorship as effectively mutually exclusive things and it ended up working out really well for me. At this particular point in time, I happened to have a manager who happened to get way out ahead of me technically, and is willing to review PRs and so, that's very nice. But it's a nice-to-have. It's not something that I expect of a manager and it's ended up making me much more happy and manage relationships.

MAE: I agree with all of that. So well said, Chelsea.

CHELSEA: I try, I try. [laughs]

Casey, are there things that you look for specifically in a manager?

CASEY: Hmm. I guess for that question, I want to take the perspective inward, into myself. What do I need support on and who can I get that from? And this is true as also an independent worker as a consultant freelancer, too. I need support for when things are hard and I can be validated from people who have similar experiences, that kind of like emotional support. I need technical support and skills, like the sales I don't have yet and I have support for that, thank goodness. Individuals, I need ideally communities and individuals, both.

They're both really important to me and some of these could be in a manager, but lately, I'm my own manager and I can be none of those things, really. I'm myself. I can't do this external support for myself. Even when I'm typing into a spreadsheet and the computer's trying to be a mirror, it's not as good as talking to another person.

Another perspective that I need support on is how do I know what I'm doing is important and so, I do use spreadsheets as a mirror for that a lot of the time for myself. Like this impact is having this kind of magnitude of impact on this many people and then that calculates to this thing, maybe. Does that match my gut? That's literally what I want to know, too. The numbers aren't telling me, but talking to other people about impact on their projects really kind of solidifies that for me. And it's not always the client directly. It could be someone else who sees the impact I'm having on a client.

Kind of like the manager, I don't want to expect clients to tell me the impact I'm having. In fact, for business reasons, I should know what the impact is myself, to tell them, to upsell them and continue it going anyway. So it really helps me to have peers to talk through about impact. Like that, too types of support.

What other kinds of support do you need as consultants that I didn't just cover?

MAE: I still need – and I have [laughs] hired Casey to help me. I still need a way to explain what it is that I am offering and what the value of that really is in a way that is clear and succinct. Every time I've gone to make a website, or a list of what it is that I offer, I end up in the hundreds of bullet points [laughs] and I just don't – [overtalk]

CASEY: Yeah, yeah.

MAE: Have a way to capture it yet. So often when people go indie, they do have a unique idea, a unique offering so finding a way to summarize what that is can be really challenging.

I loved hearing you two when you were talking about knowing what kinds of work you want to do and who your ideal customer is. Those are things I have a clearer sense of, but how to make that connection is still a little bit of a gap for me.

But you reminded me in that and I just want to mention here this book, The Pumpkin Plan, like a very bro business book situation, [chuckles] but what is in there is so good. I don't want to give it away and also, open up another topic [laughs] that I'll talk too long about. So I won't go into it right now, but definitely recommend it. One of the things is how to call your client list and figure out what is the most optimal situation that's going to lead toward the most impact for everybody.

CASEY: One of the things I think back to a lot is user research and how can we apply that this business discovery process. I basically used the same techniques that were in my human computer interaction class I took 10, or 15 years ago. Like asking open ended questions, trying to get them to say what their problems are, remembering how they said it in their own words and saying it back to them—that's a big, big step.

But then there's a whole lot of techniques I didn't learn from human computer interaction, that are sales techniques, and my favorite resource for that so far is called SPIN selling where SPIN is an acronym and it sounds like a wonky technique that wouldn't work because it's just like a random technique to pull out. I don't know, but it's not.

This book is based on studies and it shows what you need to do to make big ticket sales go through, which is very different than selling those plastic things with the poppy bubbles in the mall stand in the middle of the hallway. Those low-key things they can manipulate people into buying and people aren't going to return it probably. But big-ticket things need a different approach than traditional sales and marketing knowledge and I really like the ideas in SPIN selling. I don't want to go into them today. We'll talk about it later. But those are two of the perspectives I bring to this kind of problem, user research and the SPIN selling techniques.

I want to share what my ideal client would be. I think that's interesting, too. So I really want to help companies be happier and more effective. I want to help the employees be happier and more effective, and that has the impact on the users of the company, or whoever their clients are. It definitely impacts that, which makes it a thing I can sell, thankfully. So an organization usually knows when they're not the most happy, or the most effective. They know it, but my ideal client isn't just one that knows that, but they also have leadership buy-in; they have some leader who really cares and can advocate for making it better and they just don't know how. They don't have enough resources to make it happen in their org. Maybe they have, or don't have experience with it, but they need support. That's where I come in and then my impact really is on the employees. I want to help the employees be happier and more effective. That's the direct impact I want, and then it has the really strong, indirect impact on the business outcomes.

So in that vein, I'm willing to help even large tech companies because if I can help their employees be happier, that is a positive impact. Even if I don't care about large tech companies’ [chuckles] business outcomes, I'm okay with that because my focus is specifically on the employees. That's different than a lot of people I talk to; they really just want to support like nonprofit type, stronger impact of the mission and that totally makes sense to me, too.

MAE: Also, it is possible to have a large and ever growing equitably run company. It is possible. I do want to contribute toward that existing in the world and as much as there's focus on what the ultimate looking out impact is, I care about the experience of employees and individuals on the way to get there. I'm not a utilitarian thinker.

CASEY: Yeah, but we can even frame it in a utilitarian way if we need to. If we're like a stakeholder presentation, if someone leaves the company and it takes six months to replace them and their work is in the meantime off board to other people, what's the financial impact of all that. I saw a paper about it. Maybe I can dig it up and I'll link to it. It's like to replace a person in tech it costs a $100K. So if they can hire a consultant for less than a $100K to save one person from leaving, it pays for itself. If that number is right, or whatever. Maybe it was ten employees for that number. The paper will say much better than I will.

CHELSEA: I think that in mentioning that Casey, you bring up something that businesses I think sometimes don't think about, which is some of the hidden costs that can easily be difficult to predict, or difficult to measure those kinds of things. One of the hidden costs is the turnover costs is the churn cost because there's how much it takes to hire another person and then there's the amount of ramp time before that person gets to where the person who left was.

CASEY: Right, right, right.

CHELSEA: And that's also a thing. There's all the time that developers are spending on forensic software analysis in order to find out all of the context that got dropped when a person left.

CASEY: Yeah. The one person who knew that part of the code base, the last one is gone, uh oh.

CHELSEA: Right.

CASEY: It's a huge trust. And then engineering team is often really interested in conveying that risk. But if they're not empowered enough and don't have enough bandwidth time and energy to make the case, the executive team, or whoever will never hear it and they won't be able to safeguard against it.

MAE: Or using the right language to communicate it.

CASEY: Right, right. And that’s its own skill. That's trainable, too thankfully. But we don't usually train engineers in that, traditionally. Engineers don't receive that training unless they go out of their way for it. PMs and designers, too, honestly. Like the stakeholder communication, everybody can work on.

MAE: Yeah.

CASEY: That's true.

MAE: Communication. Everyone can, or not. Yes. [laughs]

I learned the phrase indie today. I have never heard it and I really like it! It makes me feel cool inside and so love and – [overtalk]

CASEY: Yeah, I have no record label, or I am my own record label, perhaps.

MAE: Yo!

CASEY: I've got one. I like the idea of having a Patreon, not to make money, but to have to help inspire yourself and I know a lot of friends have had Patreons with low income from it and they were actually upset about it. So I want to go back to those friends and say, “Look, this prove some people find value in what you're doing.” Like the social impact. I might make my own even. Thank you.

MAE: I know I might do it too. It's good. That's good.

CHELSEA: Absolutely. Highly recommended.

One thing that I want to take away is the exercise, Casey, that you were talking about of tallying up all of the different things that a given position contributes in terms of a person's needs. Because I think that an exercise like that would be extremely helpful for, for example, some of my students who are getting their very first tech jobs. Students receive a very one-dimensional message about the way that tech employment goes. It tends to put set of five companies that show remain unnamed front and center, which whatever, but I would like them to be aware of the other options. And there is a very particular way of gauging the value of a tech position that I believe includes fewer dimensions than people should probably consider for the health of their career long-term and not only the health of their career, but also their health in their career.

CASEY: One more parting thought I want to share for anyone is you need support for your career growth, for your happiness. If you're going to be a consultant, you need support for that. Find support in individuals and communities, you deserve that support and you can be that support for the people who are supporting you! It can be mutual. They need that, too.

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