When I first started podcasting in 2006, I didn’t possess the technology to do interviews, so I left that out of my show for a long time. One of the first interviews I did in 2008 was with a gentleman named George Tabb, a NY punk icon and early activist for those who suffered from 9/11-related sickness. While it was a bit stilted and awkward, it gave me a definite idea of the kinds of interviews I wanted to do in the future.

I think the essence of a good interview is that it isn’t an interview at all. It’s a conversation. That’s why Larry King and Howard Stern are so good at their job. They engaged in a conversation with their guests, and in doing so, they could draw more out of their guests than intended. Someone who has appeared on Stern has said they told him things they would never have spoken to anyone else. I think that’s a high compliment, and it’s certainly something I try to emulate. Last year, I did a limited series of interviews on my podcast related to how people became creatives and how they stayed creative during the pandemic. I’m biased, but I think it’s some of my best work because I think I managed to get into a personal zone with people and gain their trust during the process.

I am by no means an expert, but I do know what works for me. So I’d like to share with you five things I would do when interviewing guests.

Do your homework

If your guest has written or appeared in anything recently, you need to know about it. Read and consume anything relevant to your conversation, and maybe go beyond that. I like to ask relevant questions, but I also look for human moments in a person’s bio, social media, blog posts, and videos. If it’s funny, all the better.

Now, you may want to tell the guest you found this moment and ask if it’s ok to bring it up. Don’t go for embarrassing the guest. It’s crass, and that guest has friends who will hear about it and never appear on your show. In my experience, the human moments we all share can be a real icebreaker or pressure release during an interview. If you can get the guest to share that laugh with you, you’ve got a good conversation going.

Listen. Really.

It’s easy to get sidetracked doing other things while the guest is talking. Riding a volume level, responding to chat if this is a live stream, posting quotes on social media, and other things. I’m asking you to stop that. Your focus should be entirely on the guest and what they are saying. I have heard my share of podcasts where The host prepared the questions well in advance, and the guest said something nullified a question, only to have that question pop up later in the show. That’s an unforced error, and you’ll pay for it. The other problem with not focusing on the guest is that it becomes very awkward. Sure, you can fix long pauses between questions in Post, but the guest may have a bad feeling about it, and it will reflect in their attitude, and the quality of their performance as the interview goes on. If you realized the person you were talking to wasn’t paying attention, how long would you stick around and participate? Exactly.

Be prepared to go off the list

I want to be clear about this point. I am not saying that you shouldn’t have a list of questions or a game plan for this interview. I am saying that if you’re actively listening to the guest, they may say something that opens up a whole new line of questions you hadn’t thought about and might be worth exploring. Conversations are not linear; you can drop one thread, pull on another one for a minute, then come back to the first one. That is what makes for an organic, authentic experience for the guest and the listener. If the guest feels you are in this experience with them, chances are they’ll trust you more, and they’ll loosen up and give you the interview you want

Stay in tune with the guest

You should be getting a good read on your guest as the interview proceeds, and you should be getting an idea of places you should and shouldn’t go. If you inadvertently head down a path the guest doesn’t want to go, and they might clam up a bit, don’t push. In some cases, the guest might say something they didn’t realize would take them down that path and then give you some indication that they’d rather not. If you hit a boundary, respect it.

Know when to end it

Ideally, you’re looking for an interview to take up a substantial part of your regular podcast, but like any party, you should be looking for hints that the party is ending. The guest might start giving you shorter answers or other context clues when they start feeling like they’ve said everything they need to say. When I get to that point, I have two questions I ask to signal the guest I’m starting to wrap up. I’ll ask what they’re working on now (or next) and how people can connect with them on social media. Then I’ll thank them and wrap it up. Know when that time is coming, and don’t stretch it out. An interview that goes too long becomes awkward later, and the listeners will pick up on it.

Interviews don’t have to sound like interviews; they can be all call and response and no substance. To get to something real, don’t treat it like an interview. Treat it like you’re just talking to a new friend you want to get to know. The result is a better product for you, a better experience for the guest, and trust as an interviewer grows in your field.

I want to start this by suggesting each of us ask ourselves a question: Am I OK?

I know that might sound simple, and you might think that’s ridiculous, but I’m dead serious. I want you to ask yourself if you’re OK, and I want you to be honest with yourself about the answer.

The reason I’m talking about this is pretty straightforward, I have had to ask myself this same question, and my answer is “I’m not sure.” I’m not OK, but I’m not in dire straits or anything. I can only describe myself as being in some weird limbo state that allows some things to pass, and other things stick and drag me down a little bit for a little while. I don’t know if anyone can relate to this, but maybe you can. It wouldn’t be the first time I’ve lost my audience by talking gibberish, and it certainly won’t be the last.

Basically, I’ve spent most of my time in the company of my family or outdoors, far away from everyone else. The main human contact I’ve had is with people that share my last name. I have seen other people three times in the five months we’ve been in this state. The only time I can tell you I am in the company of other people for any length of time is on Sunday Mornings when we do the groceries. I have not done any delivery side jobs since the shutdown because I think it’s dangerous. I lost a job I absolutely loved at the end of May. I’ve been looking ever since. I’ve been doing freelance work, but it doesn’t replace my income. I wish it did.

Some of you will tell me that I’m acting like, as one friend has put it, a covidiot. There are a few people in my life that believe that this thing has been blown out of proportion, that it’s not as bad as the news has made it out to be, that it’s a big hoax, and that I’m a sheep. If that’s what you believe, you’re more than welcome to believe that. You do you. What I’m not going to do at any point is argue with people about this because that’s time out of my life that I’m never getting back, and what I have seen out of the arguments I’ve read or been a witness to is that the anti-maskers are all about demanding respect for their rights, but not willing to respect the rights of others. I’m not into recognizing your right to put me in a possibly bad situation, but I’m not going to change your mind, and you’re not changing mine, so let’s just leave it.

I realize that I will probably have to break my promise to myself that I will never take another Customer Service / Tech Support phone call, and I hate it because the second I take that job, I feel like I’ve given up. I have done many things, but giving up is not one of them. Still, coming to that conclusion has not done wonders for my disposition. It’s depressing, to be honest. I had a great job, and I want to keep doing it. I just have to figure out how, and I don’t have much of a plan as I have a bunch of ideas that barely string together to form a coherent thought.

As near as I can figure, what I need to do is post content every day and promote the heck out of it. I need to reach out to people and ask if they need something I can provide, like podcast editing or Voice work, for example. I think I’m going to create a storefront to sell my photos somewhere. I’m going to write like the dickens and get it submitted places. I would like to start making videos again, and that one seems to be the hardest button to button. I suffer from what I’ll call “Neistat Syndrome.” I just don’t think my life is that damn interesting compared to people like Casey Neistat or Peter McKinnon, and while I know I’m comparing myself to two of the tippety-top YouTubers, It’s still a thing I’m dealing with. I need to think about the format.

In the end, I think I have what Michelle Obama says is a ‘low key’ depression, maybe? I don’t feel bad, I just feel resigned to certain things and disappointed. I’m fifty years old, and that’s a factor. I indeed have more time than my parents had; there is a limited amount of time on the game clock. So I’ll do what I always do. Work, and try to pull off the seemingly impossible.

Today, I want to talk about freelancing. Not any particular line of work but the subject in general. Freelancing has enjoyed something of an uptrend lately; Lots of people were doing it before of course, but I suspect there are a lot more people doing it right now, partly out of necessity. For some, it may be how food gets on the table.

I’ve been fortunate to get a few gigs here and there, and things are working out. Did I wish I had a steady gig? Yeah. Do I wish I had, oh, I dunno, something with benefits? DUH. Am I just a little bit nervous that the Apocalypse is going to happen in a couple of weeks, and it’s all going to hit the fan? OH YEAH, TRUST ME. But right now is right now, and that’s what I need to keep a focus on. I hit the job boards every day and fill out a gang of applications, and then I hit Upwork and submit some proposals. Upwork, for the uninitiated, is a freelance job board where people post what they need, and you can submit a proposal to fill that job. If they select you, you have the gig, and you get to work. With any luck, you get paid.

I find myself wondering about the folks that are dipping their toe in these waters for the first time because I know how frustrating it was for me to pitch and pitch and pitch…and hear crickets. Contrary to popular belief, the worst thing you can hear isn’t “No”; it’s hearing nothing.

I am not going to lie to you, it took what seemed like forever to get my first yes, and before that first yes was several bites on the hook that I couldn’t reel in, but for me, the real frustration was in hearing nothing at all. Not a yes, no, hi, boo, f you…not a thing. To be honest, I have to tell you that I found it hard not to take it personally until I didn’t.

The reality check is that nobody owes you anything regarding this. They’re — hopefully — paying decent money for the result they want, and if they decide you’re not for them, there’s nothing that says they have to contact you to say “Thanks, but no.” it would be NICE, but they don’t have to do it. Once I got over that hill, it became easier to hear nothing, “No” became easier, and of course, “Yes” is just THE BEST EVER.

But let’s get back to the crickets for a second. It’s a buzzkill, for sure, and that’s where Mo comes along. It’s hard to keep going when you’re not getting anything, but that’s just momentum working against you. The overused cliche is running uphill, but it’s the most appropriate. You’ve got to spend that extra energy and dedication to keep swinging. Keep Pitching. Keep saying to the world, “I can make this for you”, and realize that you’re going to have to take no and nothing for an answer until that first person says “Yes,” and then the most amazing thing will happen. You’ll be able to show the world that one person said yes, and you’ll be able to show the world what you did with that yes, and someone will see that and add another yes to your pile. That’s when Mo comes around and starts working for you. “Yes” means results, and results attract more Yes.

I know this sounds oversimplified, and honestly, it is. But it has the benefit of actually being true! Ask any best-selling writer you can think of, and I’m sure they’ll be able to tell you some of the most hilarious and mind-boggling rejection stories before that one moment that changed their lives. How many actors and actresses, how many songwriters and musicians, how many artists were told they didn’t have what it took and that they’d never make it until they did?

We are on that same road, you and I. We’re on the highway to that town we’ll never work in again until we find there’s a house with our name on the door.

A question that is weighing on my mind lately is how much structure helps or hurts a creative. I was talking with a friend who, by all accounts, has mad organizational skills, and she runs a filmmaking business. There’s a lot of structure in her day that is taken up doing the administrative work that you need to do to run a business the right way, and she’s very good at that. However, she tells me that she spends so much time making the admin work and the proposal writing for grants and things she laments not being able to spend the time actually creating as she would like.

For purposes of comparison, I don’t have a licensed business; what I do is what I call a hobby on steroids. It could be a business. I spend so much time on the creative side that I don’t spend any time on the promotion or administrative side. So, I would be the polar opposite of my friend, as you can see. I’m sure there’s a third person out there that promotes like the dickens but doesn’t have anything created and likes the idea of calling themselves a business. Three legs on three separate stools, and every one of them is wobbly.

I’m about to say two words that I hate hearing, and I suspect a lot of us hate hearing. Time Management. We need to employ some of it. Now, I know the urban myth of the creative is some person who’s a night owl, who can’t hold a deadline with both hands, a bucket, and handles, who suffers and bleeds for his art, and haven’t we grown up enough to understand that this is simply not the case most of the time? I mean, I know one person who works all night creating clay yonis and selling gemstones on Etsy, but other than that, most of us who are creatives are day-walkers, probably with jobs. We have too much on our plate for any day, so we need to plan what those days look like. The problem is, we don’t. So, the thing that we hate doing is the one that gets put off until the Twelfth of Never.

Since I am home full time, I’ve been experimenting with time management. I block out three sections of time during the day for things. I get up at 6 am and have some quiet time before the rest of the house gets up and moving. I have a trial balloon of a project I’m trying for the first time this week that starts at 7 am, and once that’s up and running, I take the time between 7 am and 8 am to plan my day. The morning period between 8 am, and 12 pm is for new stuff. For example, this article was written during the morning period. I’ll post any blog articles, drop any podcasts or videos I’ve completed, and look at my idea pile for what I want to tackle next.

Then I take lunch and get out of the studio. If the weather is decent, I go outside and take a little walk. Generally, I take my earbuds with me, but I’m finding that this is one of those times during the day when I am by myself, and I’m finding the usual noises of being outdoors — I hesitate to call it silence — preferable. It allows me to think more clearly about what I want to be doing and not concentrate on what someone else is saying.

I return to the studio around 1 pm, and for my afternoon work period, I work on what I will call the ‘big’ project. The priority item that I would like to get shipped sooner rather than later. Right now, I have two such items, a podcast interview and a video. Both things require attention. The interview has a deadline. The video doesn’t, but I would like to get it done. So any items that require voice, or shooting, or anything like that will happen at that time. I work until 5 pm, then I shut everything down and get out of the office.

The third segment of my day happens between 7 pm and 9 pm when I do my social media for the day. I try to focus on certain hashtags. This is not posting my own work, I did that earlier that morning. This is social media outreach. I follow and commented on accounts during that time. At 9 pm, I head upstairs, put the phone on the charger, and wind down. Lately, I’ve been reading non-fiction stuff before bed. I’m out by about 11 pm if I’m doing it right.

Rinse, Lather, Repeat, as they say.

Now, there are days when I can’t keep to the schedule, if I have a Doctor’s Appointment, for example. I just don’t sweat those things when they happen because I find that getting discouraged by my schedule is the first step to not following it. As this is an experiment, I’ll be tweaking this as we go to find what’s optimal for me, but for right now, this seems to be working ok.

Time Management doesn’t have to restrict your creativity, and it doesn’t have to manage your time minute to minute. If you just lay some minimal guidelines down as to what you’re working on and when you may find that it helps move you forward with everything.