Freelancers’ Show

The Freelancers' Show discusses the challenges that freelancers face. The panel includes technology freelancers and entrepreneurs with many years of experience.

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196

196 FS On Failure


02:39 – On Failure (GitHub Issue)

03:49 – What does failure look/taste like for a freelancer?

14:22 – Irritability, Shame, and Embarrassment

20:00 – What does it mean to fail for your psyche, your family, and your position in your community?

24:33 – Warning Signs

30:13 – Should I give up or push through?

32:56 – Once you've spotted warning signs, how can you change course (especially in light of the fact that you are probably short on cash and hustling flat-out already by this point)?

39:06 – Success

Picks

Startup: A Silicon Valley Adventure by Jerry Kaplan (Reuven)
Dreaming in Code: Two Dozen Programmers, Three Years, 4,732 Bugs, and One Quest for Transcendent Software by Scott Rosenberg (Reuven)
Surprisingly Awesome (Reuven)
Brené Brown (Philip)
Draft Evidence: Essays About Design & Independent Business by Nick Disabato (Philip)

 

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TRANSCRIPT

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CHUCK: Hey everybody and welcome to episode 196 of The Freelancers’ Show. This week on our panel we have Philip Morgan

PHILIP: Hello, hello.

CHUCK: Reuven Lerner.

REUVEN: Hey everyone.

CHUCK: Charles Max Wood from Devchat.tv. And this week we’re going to be talking about failure.

I’m going to go ahead and read this. It was posted back in November to our ‘topic recommendation’ forum thing on GitHub. You can put your own in there. We put a ton in there, but if you have ideas, go ahead.

Anyway, here we go. “It’s an episode on failing in your freelancing endeavors. This could mean just failure of a particular facet of your business or outright failing as a freelancer and having to crawl back to the man and regular employment to feed your family. Maybe consider the effects of failure; what does it mean to fail for your psyche, for your family, for your position in your community? How does it feel? How do you react to learning this about you? Or how do others react to learning of this about you? How can you pick yourself back up and possibly turn it into a lesson that benefits you in the long run?”

Then he has, “But more importantly, were there warning signs? Because you haven’t had heard of failure. Once you have spotted warning signs, how can you change course especially in light of the fact that you are probably short on cash and hustling flat out already by this point? How do you know that you are indeed about to fail and not just in a lull or have to wait a little longer until a new approach finally picks up, and any other lessons learned?”

So lots of questions there. I’m curious, what does failure look like for a freelancer? Is it going back to getting a full-time job or are there other flavors of it?

PHILIP: A really good question, Mike. I don’t think there’s one definition of failure. And I know that at least as I’ve experienced it – I got some pretty good stories to share later on – it has this quality of you feel stuck, you feel like nothing’s working. I think I’ve experienced some stuff that other people would be fine as a failure but for me, it’s just like, “Well, this is a thing I got to get through to get where I want to go.”

I don’t know; maybe you guys can speak to that. I’ve never had a failure that I didn’t just take as a signal of change of direction or try something different.

CHUCK: I can see that. I was talking to my wife yesterday and I basically used the words ‘I feel like I’m failing at everything.’ And for the most part, just talking to her, I came to the realization – she coached me toward the realization; she’s much smarter than I am – that in a lot of ways, I’m not failing but in a lot of ways, I also feel like I’m not doing as much as I want or feel like I ought to. So for me, it’s mostly mental now. I have had some colossal failures in business and other things. But yeah, for me it’s the same. It’s, “Okay, well, what do I change? How do I get to another place where it’s healthier or happier or better or more money?” Or whatever our problem really is. And once you put it into context, failure is a whole lot scary and is more just a place to change, a place to move on to something better.

PHILIP: Yeah. I feel like there’s tons of things I tried and they did not work, but there was always the next thing to try or it never seem like at the end of something.

I guess for me, if I was forced to stop working for myself and start working for somebody else, that would probably feel as close to what a failure is as anything I’ve ever experienced.

CHUCK: Yeah.

REUVEN: I think they are learned from different parts and different perspectives of the failure. And one of them is just a personal failure. Like I know just – if I do a bad job with a client, I know – that’s one kind of failure. If I’m not making as much money as I need to in order to support my family, that’s a deeper kind of failure where I say, “Boy, maybe I’m just not cut out for this.” That is definitely not for me over the years.

And then part of that is a feeling of failure, part of that is a feeling of embarrassment. Like I said I could pull this off; why am I not able to pull this off? What am I doing wrong? It must be something inherent to me?

There’s another one which is we see and we talk about it, and we even interview on a show here, people who are just amazingly successful freelancers. And sometimes – I felt through the last few years, “Boy, I’ve been doing this for a long time.” And I always thought it was okay because I can pay the mortgage and everything. But I talked to these guys and wow, they just blow the pants off me. Like what am I doing wrong? I must be bad at this.

And so I think you have to put it in perspective and, say, if you’re meeting your bare necessities for income, for expenses and so forth, that’s probably a good line up of where to keep it or to be striving for. But above and beyond that, it’s just a matter of always getting better and everyone’s always improving; everyone is trying to improve.

CHUCK: Yeah. Well, you put the base line out there, being able to pay your expenses. I have a story I can tell about that.

So last summer – I didn’t publicize this much but last summer, my house was in foreclosure. And there were a number of things that came down to that. We weren’t paying any bills really. And my wife was depressed and there were a whole bunch of other things going on; it was all related.

But anyway, what happened was I was in the dumps. We could pay for food and keep the lights on but there was no way I was going to come up with any – it was $15,000 I needed to get my house out of foreclosure. And we had another house that was also in foreclosure and that was another $12,000. So it’s like, “Oh my gosh; what are we going to do?” And you’re looking at that and you’re like, “I failed.” I mean really. My family, we’re going to get a fridge box and we’re going to go live by the mail box. It is scary at that point.

Or even – I’ve been in a few situations where it’s like I don’t know how we’re going to eat for the next month and then something will work out. But it is; it’s really rough to be in that position. And then what wound up happening all just – ugh, I should save it for later to keep the suspense. But what wound up happening was I have been working on pulling together a remote conference for Angular.

So I talked to my mastermind group and they said, “If you –,” I didn’t tell them everything but I told them I was in dire financial straits. And they looked at me and they said, “Make a plan for your conference. Make a plan on how you’re going to market it and then follow the plan.” And so I did. I made a plan, I followed the plan. And I think at that inflection point was when I realized I can find a way out of this. I can make my own way out of this. And maybe I can’t but at least I’ll put myself in a position to where I can minimize most of the damage.

So I followed the marketing plan and I needed 15 grand to fix the foreclosure on the house that we live in and the conference made 24 grand. I don’t know that it would’ve nearly went that well if I haven’t been pushed along and have been motivated to do it.

It’s a terrible place to be down at the bottom, but at the same time a lot of times, that allows you to rise that much higher when you come back out of it.

REUVEN: And I think that perspective thereof also – and it’s so hard to see this when you’re there. That sounds like – I haven’t quite gotten to that point. When I’ve experienced failure, especially financial failure, it’s much like, “Oh my God, where am I going to get my money? Where am I going to get more clients? How is this possibly happening to me?” So I realized it is possible. It is possible. At least certainly I think it’s the same thing for those of us with technical skills, for those of us with these [inaudible] skills, it might mean going and getting a job but at the end of the day, you will be able to get out of it. And that’s a matter of choosing a path that you’ll find.

But believe me, I remember exactly what was happening and what was [inaudible]. But I remember coming out of it [inaudible], getting a phone call from my accountant basically telling me “you’ve got bad news going on.”

This was many years ago and it’s still – gives me a pain in my stomach hearing these sorts of things or thinking these sorts of things because you think, “Oh my God, I thought I had it all together I thought I’m really doing a great job consulting here. I tell other people what to do,” because even then I was doing that and I – it’s just a sham.

[Crosstalk]

PHILIP: What do you mean? [Chuckles]

REUVEN: Based on the thought that I can actually pull this off. Right? Because to some degree, I’ve often had – just last week, I’m saying to someone, “Yeah, I’ve been independent for 20 years and somehow I’ve still been able to pay the bills just about every month.” And it’s not a matter of “oh, somehow I’ve been able to”; it’s a matter of some of it is certainly luck and some of it is been learning the hard way. Some of it has been – it’s a business and it’s not always guaranteed to happen but it can happen.

So it definitely feels like “wow, I can’t believe this is actually going on.” I can’t believe that I’ve been able to pull this off for so many years and not have a job with a pay check for so many years, and has managed to work.

I’m still waiting in some ways for someone to say to me, “Haha! You thought you can do it! No, no. go back to your real job.”

PHILIP: I think you’re talking about my pet – I think mental illness is a wrong word for this but I have a bad case of black and white thinking where I’m like “it’s either this or it’s this.” I think when we think about failure, maybe a lot of us come from that perspective of “well, I’m either making this imagined standard of success or I’m a failure.”

And I think there’s a whole wonderful world of learning that can occur between those two extremes. So this might be interesting for listeners. I’m going to list out some of my bigger failures. This is a very partial list folks, so strap yourself in.

So I file Chapter 7 Bankruptcy which for our non-US listeners is the kind of bankruptcy where you don’t really get to keep much at the end of it.

I’ve had a home foreclosed on and taken away by the bank. I had credit card debt that I was unable to pay which lead to the former two things. I, for extended periods of time, failed to make enough money to cover my expenses. I’ve been fired multiple times by clients that’s largely over but that was part of the learning curve. I launched a productized service that went well for a while, did not scale and then I shut down. Early on, I got behind on my taxes and had to negotiate with the scariest department of the US federal government, the IRS, to work out what’s called an offering compromise. I’ve made bad hires and later those people had to be let go or fired. This was really just the highlights.

So I think as people are listening, they might mentally – I guess there’s a scale of pain that comes with different types of failures. And I’ve experienced some of the most stressful, painful ones. They all seem like learning experiences in retrospect. None of them would ever say, “Well, I failed and I’m not going to be paying my taxes.” [Chuckles] The US government doesn’t let you declaring yourself [chuckles] of failures and stop trying; you just – you get to keep trying. “I’m not done trying to be a home owner” or “I’m not done trying to make money as a freelancer.”

Things are much better now but yeah, I’ve tasted failure. And I think that’s one of the questions like, “What does it taste like? What does failure taste like?” It tastes like a lot of pain. And one of the things that I was mentioning before we started a bit into recording is that I think it tends to isolate you because it’s not easy to talk about or share about your failures. So that’s one of the biggest downsides.

Chuck, I’d be curious – how long did it take you to tell anybody what was going on with the house’s financial situation?

CHUCK: About four months after our [inaudible] occurred.

PHILIP: Okay. [Chuckles] Yes right. You didn’t want to tell anybody about it, right?

CHUCK: Oh, heavens know.

PHILIP: Yeah. [Crosstalk]

CHUCK: I was embarrassed. [Crosstalk] The other thing is I portrayed myself in these shows and stuff as a successful person and I just felt like I was letting people down by admitting that I had messed that up. [Crosstalk]

PHILIP: What?

CHUCK: Yeah. And I got over it and it’s like, “You know what, this is really important for people to understand.” I mean, it’s not just an automatic whatever and that I didn’t get a ‘Game Over’ sign on my screen when I – you know.

PHILIP: Right. They didn’t come and take your computer away and coach you on your Dropbox account.

CHUCK: Yeah, nobody said [crosstalk] you can get another coin to continue it; you just didn’t – you know. I didn’t have a choice. I kept continuing.

PHILIP: Yeah.

REUVEN: Although it’s much tougher. I think the lessons that I learned when I was an early consultant early on – and I’d say the lessons that I learned later on were probably tougher and harsher. But it was really once when I was like, “Well, at least it’s just me.” And the fact that I’m married, the fact that I have kids [crosstalk], every time things aren’t working out, oh my God, this is all on me. This is all on my shoulders.

If a client doesn’t pay on time and I was depending on that client’s payment to make whatever payments I needed, I’d feel pretty horrible. And by the way, I’m then extremely cranky as a result.

PHILIP: Yeah. We should do a show on irritability. [Laughter]

CHUCK: I might be [crosstalk].

REUVEN: My family is not invited.

PHILIP: The more self-employed people I talk to, the more I find that they’re all like, “Yeah, I have gone through long periods of time where I’m super irritable and just a pain to be around.”

CHUCK: Yup. My current funk is that I just – low energy, just not feeling good, unhappy with certain things. And it’s funny because just talking through it and realizing “oh, the worst case scenario is that I’m still unhappy with it.” With most of the stuff that I’m dealing with right now, it was like, “Okay. I’m going to live through this and it’s going to be fun.”

PHILIP: Uh-hm.

CHUCK: But when you really think about it, your brain just goes to Oh Crap Land and then what?

PHILIP: I’m curious if this is just an American thing. So here’s the dynamic that the emotional dynamic that happens around failure – and this is true of myself and I’m hearing Chuck say something that sounds very similar. It’s like, “Okay, this doesn’t match other people’s perception of me or the perception I want them to have with me, so I’m just not going to talk about this. I think that’s driven by shame, embarrass – I mean, Reuven, you mentioned embarrassment which is the extreme version of that is shame. [Crosstalk]

CHUCK: The other end to that though, just to quote in, is not just ‘this is the perception that other people have of me’ but the perception that I have of other people is that they don’t have these problems. And so I’m way worst off than them and I’m a loser and a failure because nobody else has these problems [inaudible] and embarrassed to talk about it.

PHILIP: Right. Our variation there of ‘what client would hire me if they knew…’ right?

CHUCK: Right.

REUVEN: Oh, that’s a good one. Yeah.

PHILIP: And I think we’re all on this show pass that fear because we talk about stuff that [inaudible]. Anyway [crosstalk].

REUVEN: The upper class just don’t [inaudible], that’s all.

PHILIP: Yeah. The shame leads to isolation and – here’s why I’m bringing this up, Chuck. You mentioned that when you fessed up in a [inaudible] version to your mastermind, they gave you an action plan and that connection with them started to turn things around.

So I don’t know if this is a United States thing where we all want to be oil paintings of success or Reuven, do you see that in other cultures? You’re more widely travelled than I am.

REUVEN: Yeah. I think it’s a universal thing. Although it’s probably safe to say that if people [inaudible] speaking especially on a business level, if I’m meeting with them or working with them, they’re not about to share with me, “Oh yes, I did this terribly and this terribly and this terribly.” Everyone start trying to put on a good front.

Yeah. I think it’s natural as humans. Look, here’s an extreme version of it, right? You always like to say or people in Silicon Valley always say “we fail fast and we learn from our failures and everything.” And yet the people we talk about in Silicon Valley, the people we hear about, the people we hear about, they’re not saying “wow, I really crash and burn.” They’re saying, “My company offers fancy catering every day and I’m making lots of money, I’m running two companies,” on and on and on. You don’t hear enough about this [inaudible] which is 90% or more of the startups and the other companies that are failing where people are probably learning a lot. And I’ve heard many stories about how investors are more – not by [inaudible] investors but that investors are looking to find people who have failed because they’ve learned a lesson and they’ll do it better next time around.

We talk about it a lot but we don’t actually hear from these people very much. We don’t glorify them very much. And yeah, there’s some shame there. It’s hard to get up in front of people and say, “Hey, this thing that I’m talking to you about that I’m claiming to be an expert in –,” what’s okay to say is, “I made this mistake a while back and I learned. And I don’t want you to have to make the same mistake.” And quite frankly, I do that a lot in my courses.

Here’s a really big [inaudible] – don’t do it. I did it a lot of times. [Chuckles] Right? But when I’m coding live, coding in front of people or when trying to explain something and I have no idea what I’m talking about and it’s obvious to everyone, that is a less [inaudible].

PHILIP: Yeah, right. Or hypothetically, I’m behind on my mortgage payment and I don’t know what to do. And I don’t have any new work in the pipe line. That’s the least fun way – the least fun moment in a failure situation to come clean and connect with people. But that’s when people are going to want to help you the most.

CHUCK: Yup.

PHILIP: That’s not a TED talk but that is a – that’s a moment where people will drop what they’re doing and be like, “Dude, let’s talk this through. Let’s figure this out.”

CHUCK: Yup. The other thing was – and I was just afraid that people were going to say, “Oh, he failed,” and then they were going to quite participating in the podcast or the other products that I had out there.

PHILIP: Uh-hm.

CHUCK: “Well, I don’t want to buy from a loser.” But it turned out, again, that audience, those people that figured out what was going on as I talked to people. And when I came clean afterward a couple of podcast – just in the context of talking like we are now – it became more evenly apparent, like you said, that those people weren’t going to leave. If anything, they were going to double down and say ‘we love what you do; here’s more help’.

PHILIP: Uh-hm. One other question Luca asked was what does it mean to fail for your psyche, your family, your position in your community?

Like I felt it the most in my psyche probably because I’m an introvert. I do remember when I told my parents that I was filing Chapter 7 Bankruptcy. And I remember that silence on the other end of the phone. [Chuckles] I’ve got enough from them a couple of times, a couple of different things that I’ve shared about my life and that really hurts. It really hurts to feel like you’ve said something that the other person doesn’t know what to say back to you about. They just don’t know what to say.

I mean eventually, it was fine in the end but it’s not easy. And again, those are the things that I think make us remain silent about it when we need support from other people.

REUVEN: I remember – I think I just read recently, someone said that Facebook is really problematic because everyone’s always sharing how beautiful their children are, how happy their lives are and how many successes they’ve had. And you get this picture of everyone else around you has just a great, perfect, fun, smiley life and you are the only one experiencing dread and problems and stress. And that’s so not true.

One of the things I enjoy about interviewing people on the show is to find out these people are so looked up to, and so I keep on saying “I wish I could be more like them”. They got issues also whether it’s personal issues or it’s business issues where they had to choose before. It makes me feel so much better like, “Okay, I’ll get there, too. I’ll learn from this.”

And I think your point also of not being ashamed, not being embarrassed but that failure is extremely important. And quite frankly, one of the groups with whom I have to speak it out more and more openly – and I think I’ve done this more than everybody over the years – is with my family. Where we open it up, I’m not sure what’s going to go on with the business at some point or I’m having problems or we’re having issues here because they have as much of an investment as I do, literally and figuratively. And they should know what’s going on but they also should – and I made this mistake where in [inaudible] where Git.

And we’re taking at [inaudible] of loans for the PhD. I assumed my wife pulled me aside and said, “Stop telling the kids how many loans we have. [Chuckles] It’s not going to be spoken to anyone. They’re just getting stressed.” And I was like, “Yeah, but it’s true and we’ll get out of it.” She was like, “That’s not the point you’re emphasizing here.”

PHILIP: How old were they, Reuven, at this time?”

REUVEN: Now, they’re 15, 13 and 10 so it was like two years ago, three years ago. And actually two of them were okay with it but my middle one’s much more the worrier. She was like, “Oh my God, I’m so worried about our finances.” So [inaudible] pulled her aside and said, “Okay, I’m glad I’m able to talk to you about things but I also need to dial back and dial back your worrying.” In every [inaudible], I check in with her and say, “Okay, you should know we’re doing okay now.” She’s very happy. [Crosstalk]

PHILIP: I’m imagining her browser history having searches ‘are children liable for their parents’ debts’? [Laughter]

CHUCK: [Inaudible] going to decorate that refrigerator box. [Chuckles]

REUVEN: But yeah, I feel like being open with my family. I remember – I think I mentioned on the show before, when I first got married, my wife said, “So how much do you make a month?” I was like, “Well it depends.” She said, “What do you mean it depends?” [Chuckles] This is the first time she encountered someone who have that sort of up and down income. And so I’ve seen this as my responsibility and maybe too much of a [inaudible] on me emotionally to say, “Yeah, I’m going to take care of this. I’m going to make sure that it’s not going to be an issue.” Which means that when it is an issue, then I feel that strongly inside of me like, “Uh-oh, you’re not doing your job right.”

PHILIP: Uh-hm.

CHUCK: Yeah, and that’s the place that I go to, too, is I worry about it and I take care of it so my wife doesn’t have to. And yeah, then it’s like – so when it’s a burden, it’s my burden.

PHILIP: For me, one of the early warning signs, maybe not at failure. I mean the way the question was phrased here, were there warning signs of – well, he said ‘were there warning signs’. So I’m taking that as not warning signs about failure but it’s anytime I’m like hesitant to do something I know I need to do, like resisting doing it, that’s usually a sign to me that something’s not right. And it may be a complete failure. It’s this sort of diagnostic for me.

I think in general, there’s a whole startup Silicon Valley frothy idea about ‘just embrace failure’ or ‘you try to fail’, quickly, you try to do a good job of failing and learn as much as you can. And ideally, sure, yeah. That sounds great, but I think way before that, you just have to try to take the fangs out of it and not be so afraid of it.

Again, I say this as someone who has resisted every failure that’s come his way, there was always a time where I was fighting it. I think it’s what, in the end, I was trying to say. Sometimes that time of fighting went on way too long. That’s one skill I’ve built up. I can say that by failing multiple times in big and small ways. If I see it coming, usually I’m like, “Okay, let’s just get this over with.” It’s like a scene in the movie where the guy knows he’s about to get punched so he takes off his glasses, [laughter] it’s like ‘go ahead and do it’. It’s kind of like that.

CHUCK: Yeah. For me, the warning signs are usually somewhere around the line of when I find myself justifying things or when I find myself uncomfortable with something and trying to hide it or trying to – because that’s just – I don’t know why, but it’s default behavior for me or something. So I hide it and I don’t talk about it. I don’t – you know. It’s not critical yet but if I don’t take care of it and if I don’t bring my wife in on it, then a lot of times it does get critical. And if I do bring her in on it, then a lot of times, we can sit down and make a plan to fix it and we can avert a lot of it. [Crosstalk] Not always.

PHILIP: There’s almost a sort of anticipatory flinch of like, “Oh, I think this is bad,” so the people in my life, they’re going to double down. They’re going to make me feel worst about this. And what a surprise to those of us who do that when they’re like, “Okay, that’s not great but let’s fix it. Let’s put our hands together and fix it.”

CHUCK: Yup.

PHILIP: That’s awesome.

CHUCK: Yeah, the other end of that, too, is that I’m embarrassed and I feel bad talking about it. For example, if I told my parents that our house was in foreclosure, my dad would’ve probably done something really dumb for himself to get us out of it.

PHILIP: He would sacrifice himself in some way.

CHUCK: Yeah. And I wasn’t comfortable about bringing it up to him either because of that because I didn’t want to put that burden on them, on my parents. So sometimes it’s hard to talk about it there, too. And for me, it’s any of that discomfort is the warning sign. Yeah, anyway, that’s kind of where I come from here is that – yeah, if I’m uncomfortable, if I don’t want to talk about it, if I want to hide it; if I’m embarrassed to even talk to my wife about it then it’s something that I need to deal with.

PHILIP: Yeah. So I definitely experienced extended periods of depression that I think come from this feeling of failure-like – and I think we should talk about ‘what is success’ because I think that’s where this whole idea of failure comes from is the inverse of success or not achieving success, and I think that that maybe part of the problem is that people see themselves failing when they’re really just learning. [Crosstalk]

CHUCK: That’s really good.

PHILIP: Yeah, I’ve definitely had extended period of depression that came from me being down on myself because I wasn’t achieving what I wanted to and I wondered if that has happened for you, too.

REUVEN: I don’t know if I call it depression but I definitely felt like, “Wow, how can this be that I’m just not making progress, I’m not getting better whether it’s financially or –.” I’ve mentioned the [inaudible] before we started the show that PhD is almost guaranteed to do that to you because the whole point of it is to make you feel really small and bad. And it worked! [Chuckles]

PHILIP: Is it like you were dying to do that? Is it like a hazing ritual of some sort?

REUVEN: Yes! Yes actually. It’s an apprenticeship.

PHILIP: Uh-huh.

REUVEN: But the apprenticeship comes with some degree of hazing where you will just be at your [inaudible] problem. They will tell you all the bad things you’ve done. And in my case, my body was like that.

The extreme version – one of the extreme parts was – so I finished by the skin of my teeth, and I got three deadline extensions. The second one I was told was unprecedented, the third one was because my adviser basically went in and beat up the graduate school people and said, “You will let him finish this.” [Chuckles]

So on that point, I was grateful to him, sort of, kind of. But three days before my defense, I was in my adviser’s office and said, “You know, you are the most unprepared student I’ve ever had known on doing a defense.” And went on and on and on about basically how I got it poorly and done nothing, and I started crying. Shockingly, right? And he was like – I don’t know what it is. Something like, “You should maybe get some therapy for this because something’s stopping you from finishing this PhD”. And my thought of course was, “It’s you!” [Laughter] You’re – but that’s an unwise thing to say.

But for much of the process, the feeling you get from your adviser is almost by design, you’re not doing it well enough, you’re not doing it – all these other people are doing great work and you are not. And I think what was hard for me was I wanted to do this. This was supposed to be a fun things. This was supposed to be a fun thing that was going to take just a few years and helps enhance my business career and other things. Instead, whereas my clients was happy with the work I was doing, here I was being beaten up by for what’s basically a very expensive hobby. And it was very upsetting to what [inaudible] says losing my time, losing money and feeling bad about myself.

At the end of the day, I had to realize, “You know what, I can walk away from this.” I don’t actually want to but that feeling of I have other things that are going on in my life that make me feel good, helps to bring me out of those feelings of upset and panic, and realize that this wasn’t a dead end, this wasn’t the end of my life. This wasn’t something that I was destined to feel forever. That definitely help to put things in perspective and then realize, “Okay, I’m going to do the best I can.” Worst case scenario? I can’t.

PHILIP: You know Reuven, I have my own internal PhD adviser that I carry around in my head. [Laughter] He sounds a lot like yours. [Laughter]

CHUCK: So I have a question. Because we’ve talked a lot of places where we failed and it seems like we’ve come out of it one way or another pretty well, pretty healthy. But one of the questions is how do you know that you’re indeed about to fail and not just in a lull or have to wait a little longer until a new approach finally picks up. So how do you know if you should give up or if you should push through? Because I always push through; that’s my default thing right?

PHILIP: Yeah, I’m a pusher through-er, and having seen that that can just drive deeper into what’s not working, I suggest people find some semi-objective external validation system. For me, it’s so easy to get in my head about, “Well, I should be making this and I’m making this,” or “this should be the way it is and it’s not getting some external validation.”

So if you’re trying to go to developing a market position for your business, getting external validation that has real value is critical rather than just doing the startup-y thing of, “Oh, I have this idea. I’m going to build something around it and just push on it for 12 months just to see what happens.” So I think that’s a big deal and then yeah, getting out of your head. I guess that’s my one point to add on that.

REUVEN: So I’ve tried to do a startup a number of years ago – probably like eight years ago or so. Doing it just after we returned to Israel, I was in a middle of a PhD, not so wise but fine. Let’s ignore that. I think it was – I feel like nine month point that I realized no one gives you this official sign that you should give up on it. It’s all up to you whether you want to [inaudible] through or when you’re going to give up.

For most people, it really won’t matter because it’s your own personal project and you’ve got some [inaudible] of money in it. But for the rest of the world, life goes on. And I think there’s a really – out of all the things I’ve learned from [inaudible] that started out, it was probably one of the most important things; that it’s up to me. Do I want to say, “Okay, enough or not?” And I definitely taken that with me in some ways where if I’m working on something, it’s not clear whether it’s going to pay off.

I do try to keep going, keep going, keep going but I think I’m more willing now, [inaudible] now to recognize that it’s not worth the investment of time, that I’m doing other things that are more interesting or better for me.

But it’s still hard for me to get up on stuff because I’m this constant optimist, and I’m always sure everything’s around the corner. Or I just have to give it one tweak and it will improve. And having to prioritize has been a painful but useful lesson for me to learn, and one I’m still learning in spates [check 32:39].

CHUCK: I really don’t have good context on this particular question because I always just push through until it’s very apparent that it has already failed, not that it’s about to fail, and then I give up.

PHILIP: Uh-hm.

CHUCK: So I’m really bad at quitting while I’m ahead.

So the other question here, and I think this is really just to a particular type of failure in freelancing is, once you spotted the warning signs – this is specifically in – you don’t have work, you’re not going to make money, whatever. How can you change course especially in light of the fact that you’re probably short on cash and hustling flat out already to this point?

And my answer to this is mostly just stop and really think about where you’re at and make a plan. That’s what happen to me with my house; that’s what happened to me several times whenever I’m into this or I don’t have any work and I don’t have any really good prospects for it. If I sit down and really think about it, there are a couple of things that usually become pretty apparent to me that I could do and that is go back to the people who have already hired me and paid me for work. I can go to the people that I know, I can go to the local community, I can go to the wider community for my podcast. And I can reach out to all these people and almost inevitably, somebody knows where work is. But just stopping and taking a breath is usually the first major step because once you sit down and you make that plan and you realize that there’s more stuff that you can do and maybe smarter stuff that you can do, then it gets a whole lot less scary and you stop running just for the sake of running and stop doing stupid stuff because you’re not thinking two steps ahead.

PHILIP: I’ve seen at least two distinct phases in my freelance career. One of them was when I was operating as a generalist and sort of hand to mouth when it came to work and have done nothing to build up my own audience, have no [inaudible] – wasn’t being proactive about managing a pipeline. So it happened [inaudible] thing if we’re going okay that there would be gaps between work. That was a different situation that I’m in now when there’s a momentum that comes from having an audience, having done the work to build up the [inaudible] definition and so forth. And so that stuff has a sort of momentum. And work comes in even when I’m not actively trying to make it come in.

So if you’re in that situation and something has failed like – I started this service My Content Sherpa which was a great idea. It was subscription content marketing. And I did some good work there but it just wouldn’t scale in a way that was compatible with my weird personality which doesn’t really want to manage a team. So that was a failure where I could afford to build something else because there was a momentum that carried me through. Whereas in the earlier part of my freelance career, I really would have had the hustle to make big changes. So it kind of depends on where you are in terms of how you manage that.

What I can say is that [inaudible] Chapter 7 Bankruptcy has consequences that last for years and years so you might want to prioritize how you respond to a failure based on avoiding the more serious consequences.

And also [inaudible] do a realistic risk assessment of what is a serious consequence for you and what’s not. Maybe firing a client is something that terrifies you but it’s not really as bad. And there’s another client waiting there to hire you.

Maybe you have a failed project and you need to resolve it by getting out of that project obviously. But honoring your obligations but still getting out of it early and moving on to something else. That would be much better than grinding out for six month and becoming down on yourself and depressed and exhausted.

So some prioritizing the risk and being realistic, and maybe getting a third party perspective on what – is it really that bad to do this versus this? These are all ways that you can navigate your way out of the failure situation.

CHUCK: Yup. Do you have anything you want to add, Reuven?

REUVEN: I found that one of the – I got an advice years ago to do a mastermind. So I’ve been in one now for I think about three years. And one of the great things I enjoyed about it is that I can bounce ideas off people. And these are people who I know and who I – they’ve seen my journey as a freelancer and as a consultant and I can share with them my successes but I can also share with them my challenges and my upsets and my failures.

We’re all there for each other and we’re all there to help each other improve. So the fact – having that group of people to bounce off of who are also in the same profession is I think very useful. Because it’s one thing to bounce it off my wife or maybe even friends, but these are other freelancers who are more or less the same boat. And on [inaudible] small number of vacations we’ve been to help each other out with advice over, “We’ve tried X, Y and Z; I’ve done that, “and it’s been really great, and/or to encourage each other when there have been problems.

It’s funny; I totally remember the period when I’d say, “Oh my God, I hope I’m going to get work for next month. What am I going to do?” And for [inaudible] of you, Philip – and you’re [inaudible] for convincing me to actually specialize in these great idea because that has definitely changed everything.

But I think back and it wasn’t that long ago when I’d be sending random emails out. That was stressful and that was depressing. That was annoying and that was worrying. And it made me wonder once again, “Gee, maybe I’m just doing this all wrong.” In every respect, I guess I was doing it all wrong. [Chuckles] I thought that – I learned that in a relatively gentle way.

PHILIP: Yeah, you can look at it that way or you can look at it like, “Well that was a transitional phase.” But I think you bring up a good point about building a support system before you need it and the mastermind thing can be that. It can be people that you routinely meet with. Having the professional layer to your support system can be nice. And when I say ‘professional’, I don’t mean hiring a therapist although that can be very good, too. I mean peers in your profession who you meet with – they can be there for you. I think we all have some story about that pulling us out of what could’ve been a failure or was a failure and making it better because you’re family’s there for you, too, for a lot of us in that way, but they don’t necessarily have the domain knowledge about what exactly to do the way that your peers might.

So I just wanted to point out that that’s an important way to prepare for the inevitable which is something’s not going to go great at some point. It’s good to have that support before you really need it.

We mentioned about talking success; I think that should be a whole ‘nother show.

CHUCK: Well it’s interesting because I think we all have this idea in our head of what success is, but it’s so vague that we don’t actually know when we get there.

REUVEN: It’s funny. I think in the last year or two, I started thinking about that more and more.

I really used to think success would be this massive consulting conglomerate and my name on the tops of large towers and everything shining over the city

First of all, it’s been a while since I’ve had any thoughts like that because I’m so passed that, but beyond that, what does success mean? I kept thinking more and more, if I can basically have enough money to enjoy – and this is on the financial front so I’m going to say we don’t have any other front – just to enjoy time with my family, maybe we can spend time together and we can do more or less the things we want. That is so enough for me. And the goal for me is no longer accumulate as much as humanly possible. It’s just having some nice time with my family and some of the things that we want.

That changes all of a sudden. It means that if I’m – if we’re able to more or less get what we want, then I can consider myself as a success. Then to bring back to your black and white thinking Philip, if I must suggest that I must not be a failure which is always an encouraging thought.

PHILIP: Yeah. Here’s why I think it’s almost – it’s on topic is because I’ve looked at my own achievement of increasing amounts of success and then realize that each time, as soon as I’m there, the idea that it would be permanent evaporates and it’s like, “What’s next?” [Chuckles] What’s the next level of success?

Okay, so I’m not in financial duress at all times. At one point, that was probably the definition of success was to be out of that and I’m not in that place anymore. So what’s next? It’s really interesting how achieving something that you defined as success is so fleeting. And that’s why there’s probably a larger talk out there. There’s something going on with that; it’s pretty interesting to me.

CHUCK: Yeah. And see for me, success up until this year, where we really sat down and said, “What do I want?” We talked about this in the goals episode. It really was just, “Oh, I’m not worried; I’m not deeply worried about anything right now.” That was success. So as long as nothing interrupted by success – in other words, as long as I was failing, I was successful. And so it was kind of an inverse of what you’ve said where if you’re successful then obviously, you’re not failing. For me, it was, “Yeah. That was exactly what it was.”

I didn’t have any major failure cases I was dealing with at the moment. Then a fire would start the next week and I was failing again.

PHILIP: You know, there’s this Maslow’s hierarchy of needs which is probably a little bit outdated by now. But I’m thinking about all my failures and the base level of needs is things like physical needs – food, water, place to live, etc. Then it goes up from there and I don’t think I’ve ever gone below the second highest level on that hierarchy of – one, two, three, four, five. So the bottom three have always, even at my most failing moments, have always been there.

So it’s interesting to keep that into context as we talk about failure and success.

CHUCK: I don’t even know if I remember what all of the things are on the hierarchy of needs.

PHILIP: Yes. It’s a sort of pyramid.

CHUCK: Yeah.

PHILIP: And one of the stuff in United States of America for someone who has a place to live and healthy food to eat and so forth, one of the stuff they’re worried about having is not having is like the top two layers of this pyramid. [Chuckles]

CHUCK: Yeah. We should do a show on what our definition of success is.

PHILIP: Yeah, I think it would be interesting. With more and more people becoming freelancers and that’s their – either the only available or their preferred way of making a living in the world. I think there’s a lot of range of what success is.

CHUCK: Yeah.

REUVEN: Absolutely.

CHUCK: Alright, well should we get to some picks?

REUVEN: Sure.

CHUCK: Alright. Reuven, what are your picks?

REUVEN: Alright. So in the wake of our discussion now, so I thought of two good books I read a while ago and another pick that’s not related. So the first book is Startup: A Silicon Valley Adventure, an oldie buddy goodie. It’s from 1996; I can’t believe that it’s actually oldie. But it’s about this guy who decides to do a startup and everything he encounters along the way. Basically, all the walls put [inaudible] are fun, fun, fun story.

I think in the end, his company kind of succeeded. It might be that it was a wild success and I guess that he actually finishes the book basically after going through all sorts of travails.

It’s usually [inaudible] as a book in terms of how does in work in Silicon Valley and the startup world, but there’s also so much failure, so many points that broke that when she says, “Oh, we can possibly continue. I’ve got to stop now,” and it continues up so we run from there.

Another one which I remember reading just a few years ago called Dreaming in Code which [inaudible], the guy who did Lotus, then decided to fund an open source contact manager program and it was a colossal failure. It was a colossal failure and so it was documented in this great book. The subtitle is “two dozen programmers, three years, 4,732 bugs and one quest for transcendent software”. I remember reading this book and thinking ‘oh my God, someone actually figured out how the software industry feels’, how at all these points, you’re so sure it’s going to work; it’s going to be great and then it doesn’t let you down. So those are two good books about software failure to look at.

The third thing I want to mention is there’s this fantastic new podcast called surprisingly awesome – that’s on Gimlet – where they’re basically taking topics that they think is probably boring and then they try to convince you that it’s really great, that it’s awesome. So they’ve done it on mold, they’ve done it on broccoli; they’ve done that on glue all which are great, but the most recent one was amazing, the “Frequent Flyer Miles”.

Now, the second half is okay, the first half is one of the best stories I’ve ever heard in terms of frequent flyer miles or in general – suffice to say a man bought out most of California’s supply of pudding and managed to fly his family around the world for more than a decade. It is totally worth listening to and a lot of fun. So anyway, those are my picks for this week. [Chuckles]

CHUCK: Alright. Philip, what are your picks?

PHILIP: Amazing. I have two picks this week. We mentioned some of the less fun emotions that come with failure, things like shame. I would encourage people to google a person named Brené Brown. She’s got a funny little accent mark with the second ‘e’ in her first name. Just google her, go find tons of things; a very well, very popular, well-done TED talk on the subject of shame. I’m into the category of emotional intelligence. I think it’s good to learn a little bit more about what it feels like to fail. She’s done a lot of interesting research around that and again, the emotional aspect of that. She actually has a book about that which I’ve not read, in which she interviewed a bunch of high achieving types and learned about their progress through failure into something else. That’s probably worth checking out. That’s my first pick.

My second pick is a Kickstarter that is happening right now, which means at a certain point, this pick won’t be really relevant anymore but it is right now. My friend Nick Disabato is working on, finishing up a book called Draft Evidence and that’s on Kickstarter. So if you go to Kickstarter and type in “draft evidence”, you’ll find the book and you’ll have an opportunity to contribute to it if you want. When it comes to [inaudible] paper book that details some of how Nick runs his business and some other interesting, fun stories as well. I think that’s worth checking out if you’re interested in some of the inner workings of being a solo freelancer or consultant and being successful at it despite the many challenges that come your way. Those are my two picks for this week.

CHUCK: Alright. I’m just going to quickly remind folks that I am travelling and I would like to meet you. In May, the JavaScript Jabber and Adventures in Angular podcasts are going to be at ng-conf in Salt Lake City. Now I live a half hour from Salt Lake City, so it’s not like people around here can’t just meet up with me at regular code meet ups, but if you’re there for ng-conf or if you want to just come meet some of the other folks on the shows, then by all means, come do that. I think we’re going to do the meet up then on May 5th. Then on July 9th, I’m going to do another meet up and that would be on Chicago. So if you are in Chicago, then check that out. I’m going to be there for Podcast Movement which is a podcasting conference.

Anyway, just putting all of that out there. I’d love to meet people. The best way to get information about these coming up is to join the mailing list. So if you go to freelancersshow.com, you can actually get the top 10 episodes of The Freelancers’ Show in your inbox and that automatically adds you to the list so I can reach out to you unless you know what’s going on. And you’ll also be subscribed so that you can get emails whenever we put out a new episode of the show.

Anyway, those are – I guess that’s on big, long self-promotion pick but there you go, I’d like to meet you. So I’m picking you, the audience. [Chuckles]

Alright, well let’s go ahead and wrap up the show. Thank you to the panel for being here. We’ll catch you all next week.

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