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The Sideman Designer is a podcast for creative minds, companies of one, and the people both behind the scenes and front of house making great work happen.
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Do you wish you were in control of your financial picture? Are you destined for more than the 9-to-5 grind? MMMW is here to help you see beyond your day job and build a successful web design business on your own terms. No matter what stage you’re at in your freelance journey, listen along for super valuable insights on launching, growing, and scaling a creative side hustle. Host Tom O’Malley shares proven strategies, tips & tricks that have earned him over $1 million building websites on nig ...
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From Pins to Profits with Chris Morris
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1:02:01
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Charleston local, Chris Morris, took a chance on pop culture enamel pins and it really paid off. He has since used his self-taught ecommerce experience and marketing strategies to help retail shops grow their business online. In this episode, we get into how The Midnight Society came to be and the doors it has opened for Chris’ new web design side …
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In my 15+ years as a professional website designer, I’ve learned how to make money while making clients happy. Now that I’m running my creative business full-time, it’s important to look ahead. In this episode, we’re talking big picture; what do I ultimately want this company to be? What do I want my future to look like? I’ve hit my initial monthly…
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In this episode of MMMW, we’re sitting down for a chat with Tom Jepson to discuss his thriving UK-based freelance business. With over 15 years of experience in the creative space, he’s picked up some priceless insights to share on our show. In addition to his accomplished career in user interface design, Tom is passionate about helping people like …
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Sure, website design can be fun and fulfilling—but that’s not why we do it. Freelancing is all about the MONEY. In this episode of MMMW, I’m opening my books and sharing what I charge; what I make; and how I bill my own clients. We dive deep into pricing, invoicing, taxes, and everything in between. By offering total transparency into the inner wor…
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In this debut episode of MMMW, I’m discussing what freelance means to me—and what it can do for YOU. I’ve been at this for over 15 years and can’t wait to share my story. If you want to make extra money building websites, my love letter to freelancing will get you hyped for what’s next! Let my journey from free work to 5-figure deals be your inspir…
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Burning Freelancer Questions (1st Edition)
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16:02
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In this episode of MMMW, I’m answering five burning questions from real people about running a creative freelance business. We get into passive income streams, the future of web design, side hustle ethics, WordPress themes, and finding high-paying clients. No matter what stage of the freelance journey you’re on, chances are, you’ve asked yourself t…
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Episode 022 - Read more; it's good for you
10:27
10:27
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Thanks for coming back! I've surprised myself here. I wasn't actually expecting to bring the podcast back at all until later in the year. But, such is life; full of surprises. Box of chocolates something something... This week; why I haven't been reading enough and why you should read more.
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Episode 021 - Creative Conversations - Robert Skrobe
57:41
57:41
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This episode - the TENTH in Season 2 and the TWENTY-FIRST overall! - holds another Creative Conversation. This time, I sit down with GVDS and Dallas Design Sprints founder Robert Skrobe. We talked about Design Sprints in general, the GVDS event, bringing communities together, and what might be next for collaborative design activities. Robert gives …
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Episode 020 - Tie Your Shoes Before Stepping Out!
11:14
11:14
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EPISODE 20! Amazing stuff. I wanted to bring you another Creative Conversation this week, but the Tech Gods were conspiring against me. Instead, you've got a brief ramble-cast to get you to work. I chat GVDS, Death Stranding, 'The Power Of Moments', and consider why you need to tie your shoes before you leave the house (or something to that effect!…
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Episode 019 - Creative Conversations - Helen Joy
53:35
53:35
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Welcome back! This week I had the opportunity to sit down with my good friend Helen Joy - UX researcher, speaker, and tech community advocate - to talk about the work she's doing right now, the state of our communities, and inclusive design. It was a long-overdue chat; we could have gone on way longer than our hour. There'll be a Part 2 at some poi…
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Episode 018 - Anyone Who Says They Can Multitask Effectively Is Lying To You
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4:40
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Check out that clickbait title! Seriously, though... I don't believe that 'effective multitasking' is a possibility even for the most self-aware, personally in-tune amongst us. This week I had a short conversation with myself about feeling overwhelmed and how, when trying to cram too much in, we limit our capacity to do our best work. Join me onlin…
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Episode 017 - Creative Conversations - Stephen Haunts
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1:02:25
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In this episode - the latest in the Creative Conversations series - I sit down with online educator, speaker, and writer Stephen Haunts. A tenured software engineer, Stephen runs his own business creating courses for Pluralsight along with writing books on technical (and non-technical) subjects, speaking at conferences around the globe, along with …
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In this weeks' episode, I talk about getting showered with shade online! With every post, every comment, and every ‘share’ we make, we as content creators stand a pretty good chance of upsetting someone. It’s increasingly apparent that you can’t please everyone. I want to dig in and think about a way we can (try to) make the best of a bad situation…
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Episode 015 - Creative Conversations - Charles Burdett
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41:28
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In this week's Creative Conversation, I talk to Charles Burdett; a freelance UX consultant and the creator of 'Workshop Tactics'. We talked about the state of workshop resources, planning and facilitating workshops, how your experience and confidence leads to developing your own style, plus the experience of designing and developing a product from …
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Episode 014 - Wherever You Are You Can Be Where The Action Is
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19:20
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In this weeks' verbose solocast, I talk about the week that was and dig into two themes that mean a lot to me: doing good work, and working remotely. I look at some thoughts sent to me from creative pros on the Twitterverse on the subject of what good work looks like and what drives them; thanks to everyone who sent commentary on that. I also dig i…
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Episode 013 - Creative Conversations - Jonathan Relf
41:06
41:06
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It's here! Episode 13 of The Sideman Designer podcast, a show for creative minds, companies of one, and the people both behind the scenes and front-of-house making great work happen. This week I am over the moon to bring you the first 'Creative Conversation'; we kick off this new format with my friend and ex-podcast colleague Jonathan Relf (@jbjon …
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Episode 012 - The One Where I Didn't Finish Anything
31:36
31:36
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Welcome to Season 2 of The Sideman Designer! In this first full episode, I talk about two fantastic books I read over the summer, give you a candid breakdown of the strategies I laid out for my business and where I got to with them and talk about distraction and how I'm managing it day-to-day. I hope you enjoy this feature-length solo-cast. Show No…
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In this pre-season warm-up, I talk about making conscious choices in your digital life, giving yourself the space to be more present and the space to have space! Season 2 of The Sideman Designer will be back in the coming weeks with some new formats, great conversations, and plenty of food for thought.…
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This week we hit a milestone: it's episode 10! In what is the final episode of the first season of the show, I talk about staying well-rounded as a designer (and a human being who is interested in, well, things!), share my summer reading list, and celebrate working for yourself and doing things your way.…
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Knowing when the time is right to ‘make a leap’ or pursue the type of people you want to work with can feel very intimidating. This week, we’re all about feeling good enough to do what you want to do as a professional and valuing ‘your take’ on whatever it is you’re doing.
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Episode 008 - Staying Healthy When Working For Yourself
19:14
19:14
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This week, I talk about something really important (no, seriously); staying healthy both physically and mentally when you work for yourself. Working in a place where we could be glued to our chair for 8 hours a day, on our own, we need to make sure we're getting up, out, and into the company of others (if only to remember how to say 'Hi, how's it g…
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Episode 007 - In the room where it happens...
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25:42
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In this episode, I share my experience of running a workshop that didn't go quite how I was expecting. There's some practical advice on staying flexible and making the most of what happens in the room. Plus, Hamilton, Stranger Things, and more...!
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I wondered how long into the lifecycle of this podcast it would take me to hit into some real 'business end' conversation... As it happens, six is the magic number! This time, I share the current lay of the land for my business, why I've pivoted away from some strategic moves I was making, and how iteration in your own business can be a really posi…
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I thought this week's episode was going to be a brief review of Warren Berger's magnificent 'A More Beautiful Question'. It turns out I fancied a bit of a ramble and dug a little deeper... Welcome to The Sideman Designer, episode five!
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Four weeks in and we're building momentum... This episode I share some great podcast I've been listening to during a week of torrential rain, plus go (sort of) deep on when quitting your job is a good idea. As always feedback, comments, and conversation are welcome!
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Episode 003 - It's Not a Case of The Mondays
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15:52
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We're three episodes in which some people might call a milestone. This week I have a small ramble about the week that was - reading, networking, and giant monsters punching each other - and go deep on why I really love a Monday morning. You could learn to love them, too!
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Welcome to episode two! Thanks for sticking with me. In this show I talk about giving away your time and why, sometimes, you just need to say 'no' to that request for a cup of coffee or a quick chat.
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In this, the first-ever episode of The Sideman Designer, I talk about getting down to business, finding focus, and keeping on track as you head towards achieving your big-picture goals. Order Paul Jarvis' Company of One here: amzn.to/2YLH8HR
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