Mid-Career Entrepreneurship: Turning Your Passion into a Profitable Venture

Oct 8, 2023 | Outplacement and Career Transition

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Mid-Career EntrepreneurshipAre you a mid-career professional looking to make the leap from employee into a successful entrepreneur? You’re not alone. More and more people are choosing to set off on their own path, turning their passion into a profitable venture and finally becoming their own boss. But it can be intimidating—especially if you have extra responsibilities like family or financial obligations holding you back.

That’s why we created this blog post—to show you how making the career transition isn’t as scary as it seems, but rather an empowering opportunity that opens up new possibilities both professionally and personally.

Keep reading for tried-and-true advice on how to start your journey towards mid-career entrepreneurial success!

Why Is Mid-Career Entrepreneurship on the Rise?

It’s not uncommon for mid-career professionals to reassess their goals and consider transitioning to entrepreneurship. In fact, this trend has been on the rise in recent years, and many of our Canada Career Counselling clients consider entrepreneurship as a career option. There are a variety of reasons for this, including the desire for more control over one’s career, the opportunity to pursue a passion project, or the potential for greater financial rewards. Additionally, many professionals who are well into their career may feel they have accumulated enough experience to be successful entrepreneurs.

Whatever the motivation, it’s clear that increasing numbers of professionals are making this mid-career switch, and it will be interesting to see how this trend continues to shape the business landscape in the coming years.

Benefits of Mid-Career Entrepreneurship

Here are several advantages of starting a business mid-way into your career.

  • Leveraging Experience: By mid-career, you have already built up a wealth of knowledge in your chosen field, and this can be invaluable when starting a business. Furthermore, you likely have established networks of contacts who can help you to get the word out about your new venture.
  • Passion-Driven: When you choose to become a business owner mid-career, you can pursue something that truly inspires you and allows you to make a difference in the world. Whether it’s launching a service business or creating a product line, owning your own business gives you the opportunity to do something that you are passionate about and make an impact on society.
  • Greater Control: As an owner, you will have much greater control over how things are done than if you were employed by someone else. You will be able to make decisions that reflect your values and beliefs, as well as shape the culture of the company according to your vision for success.
  • Financial Rewards: Mid-career ownership can also offer financial rewards that may not be available through traditional employment opportunities. Owners have access to profits from their business as well as other tax advantages associated with owning a business, such as deductions for start-up costs or certain expenses (e.g., mileage, home office, parking) related to running the business.
  • Learning Opportunities: Owning a business in mid-career also provides unique learning opportunities that may not be available through other avenues. You will gain hands-on experience with all aspects of running a successful business, such as sales, marketing, finance, operations, human resources, and customer service. This will help you build broader skillsets, furthering your professional development.
  • Legacy Building: Owning a business in mid-career can provide an opportunity to build something lasting and meaningful beyond just financial rewards or career advancement; it allows you to leave behind a legacy that can outlive you long after you’re gone—something no amount of money could ever buy! 

Challenges of Mid-Career Entrepreneurship

There are also numerous challenges involved in getting a new business off the ground.

Financial Risks

Starting a business can be an expensive endeavour, especially for mid-career entrepreneurs who may have already invested significant amounts of money in their current careers and households. You must be prepared to invest your own money and time in the venture and take on financial risk if you want to succeed. Additionally, you must be aware of the potential for failure, as many businesses do not succeed in the long run.  But don’t let this get you down, as many do!


Another challenge of this mid-life career change is the uncertainty associated with it. Starting a business is often an unpredictable journey, and there is no guarantee that it will be successful. Be prepared to face the unknown and make decisions without knowing what the outcome will be. This can be difficult, particularly if you are used to having more security and predictability.

Stress and Pressure

Mid-career entrepreneurs often find themselves under an immense amount of stress and pressure as they try to get their businesses off the ground. The process of starting a business can take months or even years, and during this time you must juggle multiple tasks while managing your finances and trying to stay motivated. This pressure can lead to burnout if not managed properly, so it’s important to find ways to manage your stress levels effectively.

Skill Gaps

Mid-career entrepreneurs may find that they lack certain skills or knowledge that are necessary for running a successful business, such as marketing or accounting. It is important to identify these skill gaps early on and find ways to fill them either through online courses or by hiring employees who possess the necessary skill sets.

Networking Challenges

Networking is essential for any entrepreneur, but it can be particularly challenging when you are transitioning from one career path to another in the middle of your life. It can be difficult to break into existing networks or establish new ones since many people tend to network within their industry or field of expertise rather than branching out into different areas or industries altogether.

Lack of Support

Mid-career entrepreneurs often lack support from family members, friends, and colleagues who don’t understand why they would want to pursue this path instead of staying in corporate life. You might encounter people who think you’re too old, unqualified, or just plain reckless for wanting to start something new. It’s important to remember why you wanted go down this path, despite any opposition from those around you.

Changing Lifestyle

Starting a business also requires significant lifestyle changes that can be difficult for those who are accustomed to having more free time during evenings and weekends due to established career patterns over the years prior. You will now have to adjust your schedule accordingly while still managing all other aspects of life, such as family commitments, social activities, etc., which can feel overwhelming at times.

Work-Life Balance

Last but certainly not least, maintaining work-life balance or wellness is key when pursuing entrepreneurship at any stage of a career. It’s easy to get overwhelmed by all the demands running your own business puts on you, but it’s important to carve out time for self-so that you don’t burn out before achieving your goals. 

How Career Transition Coaches and Counsellors Can Help with Mid-Career Entrepreneurship

  • Assessing Your Readiness for Mid-Career Entrepreneurship: A career transition coach can provide objective feedback on your skills, experience, and interests to determine if you are suited to entrepreneurship. 
  • Planning Your Mid-Career Transition: Once you’ve determined that you’re ready for entrepreneurship, a career counsellor can assist with developing a plan for making the switch. 
  • Navigating the Challenges of the Transition: Career counsellors and psychologists can help you navigate financial and emotional challenges by providing guidance on how to manage stress levels during the transition period, and how to balance family life with work demands while making this major life change. 
  • Providing Support and Accountability: Career transition coaching can help you stay motivated via regular check-ins, encouragement when needed, and help in staying focused on your goals, even when faced with adversity or self-doubt. 
  • Offering Mental Health Support: Career counsellors and psychologists are well versed in techniques that can help you build self-confidence so that you feel empowered enough to take risks in order to achieve success in your new undertaking. 

Meet Experienced Career Psychologists to Plan Your Mid-Career Transition Today

Canada Career Counselling has helped 100s clients navigate the decision to become an entrepreneur mid-career. Our career counsellors can help you create a timeline of steps for transitioning out of your current job, research potential new business opportunities, and identify potential mentors who can provide guidance along the way.

We offer career counselling services in-person from our offices in Calgary, Toronto, and Halifax, as well as online counselling across Canada. Contact us today for a free consultation.



  • Dr. Laura Hambley

    Written by Dr. Laura Hambley, a Registered Psychologist and Founder of Canada Career Counselling. Laura is a thought leader on Career and Workplace Psychology, passionate about career development, having helped individuals and organizations navigate the latest trends impacting today’s organizations since the late 1990s. She is a sought-after keynote speaker for organizations, associations, conferences, and events. Click here to learn more.

    To schedule a 15-minute complimentary consultation with Laura, email our team at [email protected] or submit an inquiry form here. You may be able to use your insurance plan or extended health benefits to cover counselling and assessment fees.