Key Considerations Before Becoming an Independent Contractor

The gig economy has revolutionized the way we think about work. 

With a rise in the demand for flexible work arrangements, many professionals are considering the leap into independent contracting. 

However, before taking the plunge, it’s crucial to weigh several key considerations.

Are You Ready for Independent Contracting?

Before you become an independent contractor, it’s essential to ask yourself if you’re ready for the level of responsibility it entails. 

Here’s what readiness might look like:

  • Skill Level: You possess a specialized set of skills that are in demand and can command a market rate.
  • Financial Stability: You have the financial cushion to survive the ebb and flow of contract work, especially the potentially slow initial period.
  • Self-Discipline: The discipline to manage your time effectively without the structure of a traditional job is crucial.
  • Business Acumen: Basic understanding of how to run your business, from marketing to invoicing, is essential.

Employee vs. Independent Contractor

The leap from employee to independent contractor is significant. Here’s how they differ:

  • Control: Employees are typically told when, where, and how to work. Independent contractors enjoy autonomy, deciding how tasks are completed.
  • Taxes: Contractors pay self-employment taxes and handle their own withholdings, unlike employees whose taxes are managed by their employers.
  • Benefits: Health insurance, retirement plans, and paid leave, often provided to employees, must be self-managed by contractors.

Unique Challenges of Independent Contracting

Independent contracting is not without its challenges:

  • Irregular Income: The feast-or-famine nature of contract work means income can be unpredictable.
  • No Corporate Safety Net: Contractors are on their own for benefits and must plan for their own retirement.
  • Client Dependence: You may rely on a small number of clients for the bulk of your income, which can be risky.
  • Administrative Overhead: Managing invoices, chasing payments, and handling taxes requires time and organization.

The Freedom of Independent Contracting

Despite the challenges, independent contracting can be liberating:

  • Flexibility: Contractors often set their own hours and work locations.
  • Choice of Work: You can choose which projects to take on, aligning your work with your interests and skills.
  • Direct Impact: Your contributions can have a more direct impact, and the value you deliver can be more transparent.
  • Entrepreneurial Growth: Being a contractor is a form of being a micro entrepreneur, where you are the business, offering a unique opportunity for personal and professional growth.

(Note: To learn more about what it means to be a micro entrepreneur, check out this in-depth guide by Selfgood.)

A Note About The Freelancer Lifestyle

Embracing the freelancer lifestyle means welcoming a significant shift in your daily routine and overall work philosophy. 

As a freelancer, you are the master of your schedule, enjoying the flexibility to choose not only your hours but also your work environment, be it a home office, a co-working space, or a coffee shop. 

This freedom comes with the responsibility of self-discipline, as you are your own boss, accountable for managing your time and ensuring the completion of tasks. 

The social structure of the workplace is replaced with a network of clients and fellow freelancers, often leading to a more solitary but potentially more diverse set of professional relationships. 

Ultimately, the freelancer lifestyle is a blend of autonomy, accountability, and adventure, appealing to those who are self-motivated and willing to trade the security of a 9-to-5 for the independence of self-employment.

How To Get Started As A Self-Employed Gig Worker: A Quick-Start Guide

  1. Assess Your Skills and Services: Identify what services you will offer based on your strengths and skills that are in demand.
  1. Market Research: Understand the market demand, know your competition, and set competitive rates.
  1. Create a Business Plan: Outline your business goals, strategies, and financial projections.
  1. Legalize Your Business: Register your business, obtain necessary licenses or permits, and understand the tax implications.
  1. Set Up Financial Management: Open a business bank account, set up bookkeeping, and consider how you will manage your taxes.
  1. Build Your Brand: Develop a professional brand identity, including a business name, logo, and a website.
  1. Develop an Online Presence: Create professional social media profiles and consider platforms like LinkedIn to network and market your services.
  1. Networking: Join freelance networks, industry groups, and local business events to make connections.
  1. Find Your First Gig: Use freelance job boards, social media, and personal networks to find your first contract.
  1. Deliver Quality Work: Ensure high standards in your work to build a positive reputation and encourage repeat business and referrals.
  1. Review and Adjust: Regularly review your business plan and strategies to adapt to the market and grow your business.


The decision to become an independent contractor should not be taken lightly. It requires a mix of self-assessment, understanding the differences from traditional employment, acknowledging the potential challenges, and embracing the freedom it provides. 

If you’re ready to take responsibility for your work and you thrive on flexibility and self-direction, becoming an independent contractor could be a rewarding next step in your professional journey. 

Just remember, as a micro entrepreneur in the burgeoning gig economy, the success of your venture will depend heavily on your ability to adapt, persevere, and manage your business with the savvy of a seasoned professional.

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