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Tips for Success in Self-Employment: Lessons from “Successfully Self-Employed” by Gregory Brennan

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By Eric Johnson March 31, 2023 2 Min Read

Being self-employed can be a rewarding and fulfilling career choice, but it requires dedication, planning, and perseverance. In his book, “Successfully Self-Employed” (Upstart Publishing Company, 1996), Gregory Brennan offers valuable advice and insights for individuals pursuing this path. In this article, we will explore some key takeaways from Brennan’s book that can help you become more successful in your self-employed ventures.

Preparation and Professionalism

Brennan emphasizes the importance of being prepared when meeting with prospective clients. He suggests creating a list of questions to ask during your first visit with a prospect, as it shows that you are focused, professional, and interested in their needs. Moreover, it allows you to listen and take notes without worrying about what to ask next.

As the saying goes, “Luck is simply being prepared to take advantage of opportunity” (Successfully Self-Employed, p. 102). One way to appear more professional is to present polished proposals to your prospects. Brennan recommends getting your proposals bound or made to look presentation-like and making multiple copies to share during meetings.

Persistence and Asking for the Business

In self-employment, persistence is crucial. Brennan points out that 80% of all new sales are made after the fifth call on the same prospect. To turn a prospect into a client, you must be proactive and not afraid to ask for the business. He advises asking two critical questions during meetings: “If there was one thing you could change about the way your vendors are currently doing business, what would that be?” and “Do you have a project now or in the foreseeable future in which I could play a role?” (Successfully Self-Employed, p. 162).

Planning and Adapting

Planning is essential for success in self-employment. Brennan encourages individuals to plan every aspect of their business, from calls to clients and prospects to projects and proposals. Having a plan allows you to adapt or change directions when necessary.

However, Brennan also suggests allowing serendipity to play a role in your business. By staying curious and open to new opportunities, you can discover new avenues for growth and success.

Networking and Relationship Building

Your network is the lifeblood of your self-employed business. Building and maintaining relationships with clients and prospects is crucial for securing referrals and support. Brennan advises staying in touch with your network and nurturing relationships to ensure continued success.

Managing Finances and Overhead

Keeping overhead low is essential for reaching profitability quickly. Brennan recommends setting up a home office to eliminate the expense of renting a separate space. Additionally, he advises monitoring your bottom line and ensuring that you don’t give away work for free, as no volume of business can make up for that loss.

Embracing Opportunities and Overcoming Challenges

Being self-employed means facing challenges and setbacks. However, Brennan argues that success is a process of incremental steps forward and occasional stumbles backward. By persevering and taking advantage of opportunities, you can increase your chances of becoming successfully self-employed.

In conclusion, Gregory Brennan’s “Successfully Self-Employed” offers valuable advice for individuals seeking to excel in self-employment. By following these tips and learning from Brennan’s experiences, you can better prepare yourself for the challenges and opportunities that come with being your own boss.

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