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17 things I wish I knew before working online | DS599 | Doug.Show

3.7K views· 21 likes· 48:45· Jan 12, 2026

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I've been working online, self employed for over 10 years. Here are some things I've learned. Brought to you by Semrush Affiliate Program https://nichesiteproject.com/semrush-affiliate Promote the Semrush Affiliate Program, which offers high commissions (up to $300 per sale) and a long 120-day cookie window, by highlighting their new AI Visibility Toolkit that solves the current business pain point of tracking brand presence on AI platforms like ChatGPT and Google AI Mode. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. https://nichesiteproject.com/giftlab *I'm an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy https://milehighfi.com/store Join My Email list https://nichesiteproject.com Mile High FI Podcast @MileHighFIPodcast Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 --- FREE! Get all my TEMPLATES and SYSTEMS https://nichesiteproject.com About Niche Site Project: http://nichesiteproject.com/about/ DOUG CUNNINGTON, PMP writes about Affiliate Marketing, Niche Sites, SEO, productivity, project management. His work has been featured all over the web, including Ahrefs, SEMrush, Empire Flippers, Niche Pursuits, Side Hustle Nation, The FI Show and more. He's a Project Management Professional (PMP, certified in 2008 by the Project Management Institute). From the old, corporate days, and the PM skills come in handy. 00:00 Introduction 00:31 Using AI for Content Creation 02:07 Starting the Online Journey 03:25 The Reality of Working Online 05:55 Financial Potential and Challenges 10:50 Flexibility and Workload 17:20 Managing Multiple Projects 19:32 Income Variability and Financial Planning 22:51 Isolation and Human Interaction 24:51 Mastermind Groups: A Hack for Isolation 25:24 Sales and Self-Marketing Essentials 26:46 Managing Your Tools and Expenses 31:27 The Importance of Continuous Learning 32:29 Dealing with Burnout 36:12 Focusing on Long-Term Goals 37:44 The Reality of Success and Change 41:10 Planning Your Exit Strategy 42:45 Separating Identity from Work

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