---
title: Freelancing & Solopreneurship
description: Freelancers and solo founders sell skills or products without a team. You will learn finding clients, pricing and contracts, taxes and admin, productising services and building an indie business.
category: business-entrepreneurship
subcategory: entrepreneurship
difficulty: beginner, intermediate, advanced
url: /subject/freelancing-and-solopreneurship
---

# Freelancing & Solopreneurship

Freelancers and solo founders sell skills or products without a team. You will learn finding clients, pricing and contracts, taxes and admin, productising services and building an indie business.

## Available Resources

4 Books • 2 Websites

## Podcasts

### 1. The Side Hustle Show

**Author:** Nick Loper

Long-running interview podcast hosted by Nick Loper in which guests explain how they started and grew side businesses, including freelancing, online stores, content sites and service gigs. Listeners get concrete tactics for launching and scaling income beyond a day job.

**Difficulty:** Beginner | **Language:** en | **Price:** Free

**Link:** https://www.sidehustlenation.com

**Tags:** side-hustle, freelancing, online-business, solopreneurship, small-business

### 2. The Speaker Lab

**Author:** Grant Baldwin

Weekly podcast from Grant Baldwin and his coaches on building a paid speaking business: finding and pitching events, setting and negotiating fees, marketing a speaker brand and interviewing working professional speakers. Listeners learn how conference and keynote speakers get booked repeatedly.

**Difficulty:** Beginner | **Language:** en | **Price:** Free

**Link:** https://art19.com/shows/the-speaker-lab-podcast

**Tags:** professional-speaking, keynote-speaking, speaker-fees, speaker-marketing, getting-booked

### 3. Creative Pep Talk

**Author:** Andy J. Pizza

Weekly podcast by illustrator and author Andy J. Pizza on sustaining a creative practice, through solo episodes and interviews with working artists about discipline, finding a creative voice, overcoming blocks and building a viable career from creative work.

**Difficulty:** Beginner | **Language:** en | **Price:** Free

**Link:** https://www.creativepeptalk.com

**Tags:** creative-practice, creative-careers, illustration, creative-discipline, artist-interviews

### 4. Art Side of Life

**Author:** Iva Mikles

Interview podcast in which illustrator Iva Mikles talks with working artists about their careers. Conversations cover finding clients and commissions, freelance illustration, building a personal style, social media audiences, and daily studio habits, showing how professionals sustain creative work.

**Difficulty:** Beginner | **Language:** en | **Price:** Free

**Link:** https://artsideoflife.com

**Tags:** art-career, illustration, freelancing, artist-interviews, creative-habits

### 5. The Creative Boom Podcast

**Author:** Katy Cowan

Interview podcast from the Creative Boom magazine in which Katy Cowan talks with designers, illustrators, animators and creative founders about their careers, including confidence, burnout, pricing and sustaining work. Listeners hear how working creatives build durable practices.

**Difficulty:** Beginner | **Language:** en | **Price:** Free

**Link:** https://www.creativeboom.com/podcast/

**Tags:** creative-careers, creative-process, burnout, illustration, graphic-design

### 6. Startups For the Rest of Us

**Author:** Rob Walling

Long-running interview and question-and-answer podcast for self-funded software founders, hosted by the founder of MicroConf and TinySeed. Episodes cover pricing, churn, hiring the first employee, marketing channels and moving from freelancing to a product business.

**Difficulty:** Intermediate | **Language:** English | **Price:** Free

**Link:** https://www.startupsfortherestofus.com/

**Tags:** bootstrapping, saas, solo-founders, pricing, product-marketing

## Websites

### 1. Kalzumeus Greatest Hits

**Author:** Patrick McKenzie

Essay archive from a developer who ran a one-person software business, covering first consulting clients, raising rates, salary negotiation, minimum viable back-office setup, and the path from productised consulting to a SaaS product.
First-hand, numbers-attached writing from someone who actually did it, which is the opposite of the course-seller content that dominates this domain. The curated 'greatest hits' index solves choice-paralysis across a fifteen-year archive.

**Difficulty:** Intermediate | **Language:** English | **Price:** Free

**Link:** https://www.kalzumeus.com/greatest-hits/

**Tags:** freelancing, consulting, pricing, solopreneurship, essays

### 2. Self-Employed Individuals Tax Center

**Author:** Internal Revenue Service

Official IRS hub for sole proprietors, independent contractors and gig workers, covering Schedule C, Schedule SE self-employment tax, Form 1040-ES quarterly estimated payments, 1099 information returns, business structure choices and the home office deduction.

**Difficulty:** Beginner | **Language:** English | **Price:** Free

**Link:** https://www.irs.gov/businesses/small-businesses-self-employed/self-employed-individuals-tax-center

**Tags:** self-employment-tax, taxes, irs, sole-proprietor, estimated-taxes

## Books

### 1. Value-Based Fees: How to Charge What You're Worth and Get What You Charge (3rd Edition)

**Author:** Alan Weiss

Method for pricing solo consulting work on client outcomes rather than hours: establishing value with the buyer, building option-based proposals, handling fee objections, and structuring retainers. Third edition, aimed at independent consultants and boutique practices.

**Difficulty:** Intermediate | **Language:** English | **Price:** Paid

**Link:** https://www.amazon.com/dp/1119776929?tag=edmonddante07-20

**Tags:** consulting, pricing, value-based-pricing, proposals, freelancing

### 2. The Win Without Pitching Manifesto

**Author:** Blair Enns

Twelve proclamations on how independent creative and consulting firms can stop pitching for free, specialise, control the sales conversation, qualify clients early and say no. 144 pages, written by a new-business advisor to creative firms.

**Difficulty:** Intermediate | **Language:** English | **Price:** Paid

**Link:** https://www.amazon.com/dp/1605440043?tag=edmonddante07-20

**Tags:** consulting, sales, positioning, client-acquisition, creative-business

### 3. Working for Yourself: Law & Taxes for Independent Contractors, Freelancers & Gig Workers of All Types

**Author:** Stephen Fishman

Nolo's legal handbook for the self-employed: choosing a business structure, worker-classification rules, drafting client agreements, insurance, recordkeeping, deductions, estimated taxes and getting paid. Written by a tax attorney and revised regularly for current US law.
The one book that covers the unglamorous half of solo work - entity choice, 1099 vs W-2 classification, contract clauses, deductions - with actual legal citations instead of anecdotes.

**Difficulty:** Beginner | **Language:** English | **Price:** Paid

**Link:** https://www.amazon.com/dp/141333217X?tag=edmonddante07-20

**Tags:** self-employment, taxes, business-law, contracts, independent-contractor

### 4. The Prosperous Coach

**Author:** Steve Chandler, Rich Litvin

Steve Chandler and Rich Litvin argue that coaching practices grow through direct conversation and referral rather than marketing funnels. The book covers creating clients, pricing, and holding bold conversations that convert prospects into committed paying clients.

**Difficulty:** Intermediate | **Language:** English | **Price:** Paid

**Link:** https://www.amazon.com/dp/1600250300?tag=edmonddante07-20

**Tags:** coaching-business, client-acquisition, sales-conversations, pricing, executive-coaching

## Youtubes

### 1. F*ck You, Pay Me

**Author:** Mike Monteiro

Thirty-eight minute CreativeMornings talk in which a design studio co-founder and his lawyer explain contracts, scope, kill fees, payment terms, chasing late invoices and when to walk away from a client. Recorded San Francisco, March 2011.

**Difficulty:** Beginner | **Language:** English | **Price:** Free

**Link:** https://www.youtube.com/watch?v=jVkLVRt6c1U

**Tags:** freelancing, contracts, client-management, invoicing, design-business

---

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