Are you a working professional who is trying to figure out:

  1. If you should pursue a second job, whether starting a side business or working for two employers at the same time?
  2. How to go about finding a second job?
  3. How to maximize your performance at two or more jobs?

Or are you a student ready to start your career, a blue-collar professional, or a stay-at-home parent looking to supplement your income or to fulfill your professional dreams and goals?

Then this is the book for you.

With practical advice and an insider’s perspective on how businesses work and how managers think, this guide will help you not just start a second job but thrive in it while not letting your primary job and primary relationships suffer.


The pandemic, job losses, the Great Resignation, rising inflation, and the dramatic increase in the cost of living has caused an explosion in information about side gigs and the gig economy. However, 99 percent of that information focuses on what side gigs to do and how to do them. There is almost nothing about how to integrate that side job into your current personal and work life to avoid burnout, legal or tax trouble, or a thousand other obstacles, so that it is not just a side gig, but a powerful tool to help achieve your financial and career goals.

Regardless of what kind of second job you take on, this book will guide you through the process of minimizing mistakes and maximizing your performance in both jobs, so that, while there are risks, you will be aware of them, be able to plan for them, and overcome them. This book will help ensure that your second-job journey is a productive and successful one.

Key Features

You may assume that working for the same company for many years provides job security. This book will show you what really provides job security: diversifying your income streams. This book will show you how to improve and maintain your performance at your first job in order to build trust with your primary employer all while doing the same with a second job, so you can obtain true security.

It’s a handbook to help professionals like yourself navigate pitfalls that Human Resources often sets up to impede you from having a second job.

With this book you can understand how to jump start your second career, whether it’s a business or a second full-time or part-time job. There are many articles that tell you how to get a second job, and even on what kinds of “side-gigs” you can try, but not how to maintain your performance in that second job.

Chapter Outline


The introduction introduces you to our story, why we wrote the book, what we hope it accomplishes, and who it is for.

Section I: Setting the Stage

This first five chapters give you a “behinds-the-scenes” look at the realities of workplaces from HR’s perspective and addresses all the points you will want to know before you begin a second job.

Chapter 1: Is a Second Career Right for You?

Chapter 1 will give you a better sense of how to view your primary and secondary jobs, your reason for doing those jobs, and how your manager sees them. Too often decisions regarding money, job security, and careers are skewed by fears. This chapter will put those fears in their proper place, so you can make better decisions and see those big forces not just from your own perspective, but from the perspective of employers.

Chapter 2: Getting in the Mind of Management

This chapter will guide you through gaining and maintaining your manager’s confidence and trust by uncovering what managers really want from their employees: time or productivity.

Chapter 3: Speaking the Language of Managers

Earning your manager’s trust is step one, then you’ll need to know how best to approach management with your second job. This chapter delves into communication styles to prepare you to make a pitch that ensures your employer’s buy-in and support on your second job.

Chapter 4: Legal Matters

This chapter prepares you for all the legal matters you will need to consider and how various laws, contracts, and policies will impact your decision to get a second job.

Chapter 5: Taxes

Because taxes vary so much from country to country and year to year, this is a general guide to dramatically reduce any unknown unknowns. You will be able to start your second job having prepared for how to reduce your tax liability and avoid any tax surprises rather than learning by trial and error as you go. This chapter address tax brackets, tax liability, business tax, how taxes affect different types of employment and the pros and cons of incorporating as different business entities.

Chapter 6: Health Insurance

This chapter guides you on how to make the best decisions on maximizing health insurance coverage and how to save money when you have access to health insurance from two, or more, different employers.

Section II: Your Employer’s Concerns

These two chapters address how to prepare for and address your employers two major concerns and how to avoid risking your primary job when starting a second job.

Chapter 7: Understanding and Avoiding Conflicts of Interest

This clarifies what conflicts of interest are, their consequences, and how to avoid them.

Chapter 8: Intellectual Property

This chapter addresses intellectual property concerns and how to make sure you are not doing anything that will either endanger your job or endanger your ability to reap the rewards of your work in your second job.

Section III: The Art of Serving Two Masters

Excellent step-by-step advice on how to maintain high performance and succeed at both jobs is clearly outlined in this section.

Chapter 9: Avoiding Exhaustion

This chapter addresses the harsh reality of trying to accomplish more with the same number of hours a day. It includes practical advice and steps on how to manage your time, what you shouldn’t cut out, and how to decide what to eliminate to devote the necessary time to your second job. It also addresses managing stress and avoiding burnout.

Chapter 10: Distractions

This chapter provides practical advice on how to not only stay focused but to both be and appear productive. It guides you on how to maintain not just your performance, but your reputation.

Chapter 11: Taking the Plunge

This chapter gets into the nitty gritty of clarifying your purpose in getting a second job and how to decide what kind of second job to get. It outlines skills that will help you get that second job, and the goal-setting and time-management skills that will make sure you succeed at both.

Chapter 12: The Secret of Serving Two Masters

The secret to serving two masters is to learn to be your own master. This chapter outlines how to be a manager to yourself, including how to find and align your jobs with your life’s purpose, how to conduct performance reviews with yourself, and how to start and keep improving in your jobs and in your life.