How Do I Start a Second Career?

February 16, 2022
February 16, 2022 Terkel

List one way someone can start a second career?

To help you start a second career, we asked business leaders and career coaches this question for their best advice. From identifying overlapping qualifications to utilizing online resources, there are several tips that may help you identify and land a second career with minimal friction. 

Here are 13 tips for starting a second career:

  • Identify Overlapping Qualifications
  • Work in a Remote and Flexible Setting
  • Get Involved in Professional Associations
  • Look into the Community
  • Start a Second Career as a Consultant Or Investor
  • Rebrand Yourself to Change Your Career
  • Start by Moonlighting
  • Master the Top Skill of Your Dream Career
  • Do An Internship
  • Understand What You Want to Pursue
  • Freelance
  • Determine Your Path
  • Use Online Resources to Become Your Own Boss

How Do I Start a Second Career?



Identify Overlapping Qualifications

Most careers develop skills and accumulate experience valued in various other areas. Even if your role seems vastly different, it pays off to make an inventory of your career assets. You may pivot to a different function within the same business and leverage the knowledge of the firm structure and practices. You may transition to another industry but still work in the same type of department where the work better matches your abilities. Even if your second career is distant from the first, you may perhaps have a head start with your presentation or negotiation skills developed previously.

Michael Sena, SENACEA


Work in a Remote and Flexible Setting

A second career can best be done in a remote and flexible setting. The issue that people run into is that their full-time, 9-5 role would interfere with the second job. There needs to be a sort of balance in juggling these careers, so it’s best that the second career offers flexible hours where you can work on your own time, and it can be completed from anywhere. For some, it’s easier to sit in the home office and put in some hours on the weekends, which is a great time to work on the second role. When you can find a happy medium in both positions, especially where one offers a flexible and remote environment, you will set yourself up for success.

Lance Herrington, UNICO Nutrition


Get Involved in Professional Associations

Starting a second career is more than just picking a field that may interest you, it’s about learning the ins and outs of that profession from the experts, and that’s why joining a professional association is a great option. Understanding a field requires knowing the details of a profession that are not on the surface, from required skills to expenses.

Professionals associations offer conferences, networking opportunities, and access to continuing education programs targeted toward your field of interest. Through these associations, you can gain access to experts and professionals who can provide you the career advice and other details necessary to advance your goals and move you closer to a second career.

Cody Candee, Bounce


Look into the Community

Consider your local community and their needs for a second career. It can be something as simple as a babysitter or a dog walker for the neighbor across the street. This requires little time commitment and some training, such as CPR for children, as an example. For someone looking for an easy commute and extra cash, look locally for opportunities.

Corey Ashton Walters, Here


Start a Second Career as a Consultant Or Investor

Veteran professionals that have the opportunity and resources to start a second career can do so by leveraging their experience and field expertise to invest in new or young business opportunities. The investment can be in either time or money, whether serving as a consultant to young professionals or providing the startup capital to encourage new business growth. Starting a second career can also be the chance for you to branch out to a different field, while still utilizing your extensive background to work effectively with potential customers and identify true business potential.

Brett Estep, Insured Nomads


Rebrand Yourself 

Businesses are always looking for ways to cement their brand into the minds of the public so they are readily identifiable in a market space, and this technique is also useful for those looking to start a second career. How one presents their image to the public can set ideas about a person’s capabilities, attributes and skills.

Updating your image, adjusting your profile to meet the qualities specific to the career you want to pursue, changing your email template, and altering your resume to highlight specific skills, are all ways of rebranding yourself to prospective employers. By looking at your messaging on social media platforms and other forms of communication, you can change your brand, which will give you great opportunities to change your career track.

Adelle Archer, Eterneva


Start by Moonlighting 

While most people’s gut instinct, once they’ve decided to pursue a different career path, is to make a clean break and dive right in, I would suggest the opposite. Don’t just make a leap of faith and hope for the best. More often than not, we’re being pushed by inherent optimism bias, and this blind leap won’t end well. Rather, the more reasonable approach is to ease into your new career. 

Whatever it is, start by moonlighting with a part-time gig or freelance work. This might not be the satisfaction you’re looking for, but it will inform whether you’ve made the right choice before you actually make it. For example, imagine you want to quit your job as an accountant to pursue a career in photography, which is your passion. However, what you may discover is that while photography is fun on the weekends and on trips, it might not be fun dealing with bossy clients or demanding scheduling. It’s much better to take things slow.

John Ross, Test Prep Insight


Master the Top Skill of Your Dream Career

If you are looking to change your career path, one of the most important things you can do is find out the most valuable skill for that career and master it. Take courses and maybe even get a certificate if possible. Find ways to practice as much as possible. Become the master of the craft, and you will be ready to pursue that new career aspiration confidently.

Ann McFerran, Glamnetic


Do An Internship

Get some full-time professional or academic training. Doing an internship can be helpful, and most companies offer them. Seeking out classes in whatever industry you’re interested in can also give you a leg up toward a second career. Choosing a new career path is never easy and can be a challenging time, but taking the time to do some career planning will get you on the right track.

Phillip Akhzar, Arka


Understand What You Want to Pursue

The first step you should take is understanding what you want out of this new career field. Are you pursuing it to make more money or is it something you are passionate about? Most people at some point or another wonder what it would be like if their career was something different so do not be afraid to pursue it. It is never too late to pursue something new. Once you figure out what you want to pursue you need to understand how you can obtain the skills required for that career path. Maybe you have to go back to school, time management skills will definitely come in handy so get yourself a nice planner.

Mark Jorgensen, CTL



Improving and creating new skills takes practice. You can start your second career by practicing the skills required for your second career through freelancing. Freelancing will help you gain experience in a new field and compile a portfolio of work to display when switching careers. 

Liz Hogan, Find My Profession


Determine Your Path

Ultimately, you need to determine whether you intend on keeping this as a side hustle or if you’d like this to replace your day job altogether. If you plan on monetizing something you enjoy doing, maintaining it as a side hustle is a great way to avoid stressors that might lead you to resent what you once enjoyed. Alternatively, if you plan on scaling your operations to replace your primary form of income, then focusing on the skills and expertise that you’ve developed throughout your career can allow you to create something that you’ll be able to grow rather quickly.

Riley Adams, CPA, Young and the Invested


Use Online Resources to Become Your Own Boss

For those wanting to follow their passions and form their own business, becoming an entrepreneur would be the fast track to starting a second career. There are numerous resources that can help get you started. For example, ENTRE, which is the leading online education platform for both aspiring and current entrepreneurs. WordPress for an easy website template. Legal Zoom to form your LLC. Quickbooks or Freshbooks for easy accounting. And Canva is a great app/website that makes it easy to create brochures, marketing materials, and social media posts.

Kendra Riley, Dawning Public Relations


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