Self-employment reflection exercise

Self-employment brings to mind the image of the savvy business owner or fiercely independent freelancer. But as self-employment rates increase globally, many turn to it out of necessity.

For example, Australian researchers found that mothers with children under 12 chose self-employment at more than double the rate of other female workers. The mothers opted for entrepreneurship because it’s the only additional income stream that lets them balance work and family.

Other people freelance as a way to fulfill their dream careers or curate their work to their lives.

Regardless of the reason, many people aren’t ready to handle the complete independence and responsibility of self-employment. It comes with a unique work environment, roles, and tasks alongside other considerations not suitable for everyone’s individual situation or temperament. 

Here are some ways to make transitioning into self-employment easier.

1.  Self-Awareness

Though it may seem obvious, knowing yourself in a work context is essential to a successful career transition. So, try to figure out what types of job duties and skills you can handle or learn. For example, I know I’m not suited for a carpentry career. This is because I lack the patience and bravery to work with carpentry machinery despite having the necessary resources to up-skill. Similarly, you can consider whether the following critical aspects of self-employment are something you can do, learn, or at least tolerate:


Freelancing means being your own boss. Ask yourself, can I handle overseeing every aspect of my career? Can I handle dealing with schedules, clients, products, and finances independently?


Self-employment can mean working alone. Can you handle working alone or working with others infrequently? If you can’t, what are some of the ways you can mitigate the effects of isolation at work?

Work-Life Balance

Being self-employed can make finding a work-life balance more difficult. Ask yourself, what sort of work-life balance do I want? How will I keep these two domains separate when I work from home and make my own schedule?

Skills Transfer

Transferable skills are vital to any successful career transition, and freelancing is no different. Consider your strengths and weaknesses in the context of self-employment. Ask yourself, am I independent, good at time management, planning, or budgeting? Do I have the skills for my career path, or do I know what I need to improve?

2. Adjustment 

Like any significant life change, a career transition impacts your relationships, routines, and identities. The transition into self-employment is no different, as you try to adjust to a new lifestyle and skillset compared to what you had in your previous career. Here are some tips on how to adjust to this transition:


Creating and maintaining a robust social network can help ease any career transition, especially when it comes to freelancing. Networking is an integral part of building a robust loyal clientele. Strong relationships can help also you combat isolation and overcome obstacles.

Ask yourself, Who do I already know that can support me in this new endeavour?  (See Relationship Inventory)

Identity Change

All major life transitions can drastically affect your identity; career transitions are no exception. Dealing with this identity change can be the key to a positive adjustment. Think of it as expanding your identity rather than tossing your past aside.

Ask yourself, What has changed? Am I trying to replace or add?


Career transitions are emotionally and mentally challenging. Many feel they need to mourn their previous careers before settling into new ones. So, let yourself grieve that old career and way of life, but don’t wallow in it. The key is to go from concentrating on your emotions and the past to your actions and the present.

Ask yourself, What am I upset about, and what can I do to address it now?


Humans are habitual creatures. We all have work routines that work for us. Unfortunately, those work routines are disturbed when you make career transitions. For freelancing, intentionally creating meaningful work routines that fit your new work-life balance and setting helps with the adjustment process.

Ask yourself, What kind of routines do I do the best in, and how can I make that work in my new situation? What are the bad habits that I need to work around?

3. Retirement

Retirement is an often-overlooked aspect of self-employment. Self-employed workers don’t have the same level of governmental and organizational support that their employed counterparts have when it comes to retirement planning. Furthermore, research indicates that the reason for self-employment, forced or voluntary, can impact retirement savings habits and pension plan optimism.

But retirement involves more than financial planning. When and how you retire can also drastically impact your retirement experience. Here are some tips on how to plan for retirement while self-employed.


The most crucial part of planning for retirement is deciding the kind of lifestyle you want to have. For example, do you want to continue working, try volunteering, or go traveling? Even if you prefer a more idyllic lifestyle, having daily activities helps ease the transition.

Volunteering is a popular option, as it helps you to find purpose, and have community without the workload of a full-time job.


It’s important to consider saving for retirement when you’re self-employed. A key aspect of financial planning is deciding what kind of post-retirement lifestyle you are saving money for. This can help you create concrete and realistic retirement-saving goals.

Also, remember that you don’t have the standard pension plans that other workers do. Try reaching out to experts to find out how you can start contributing to your retirement plans.


Another key factor is knowing when and how to retire. There is no “right” time to retire, as many are going in and out of retirement or never fully retiring. Furthermore, no one should dictate how you retire.

For many, easing out of retirement by going from full-time work to part-time and then casual work is better than retiring completely. Ask yourself how and when you want to retire, keeping in mind your personality, goals, and lifestyle. 

Acknowledging the process

Making the transition into retirement is a complicated process. It’s a significant life change that can drastically impact your lifestyle, relationships, and mindset.

A vital aspect of a positive transition into retirement is intentionally moving toward acceptance. Whether you’re retiring out of your own choice or not, learning how to grieve and let go of the past is one way to start finding joy and peace in your new position. For example, you can try seeing retirement as your chance to travel and explore hobbies instead of just the end of your career.

4. Work Environment (home office/space)

Planning your work environment is important to your own productivity, as well as the function of your home. You want to consider the setting. If possible, it is best to have a separate, designated space for a home office. This allows for more focus, and a separation of your work and home life.

Plenty of storage space is also something to consider, especially if you are unable to have a distinct office area. Storage space means you have a place to put your things, leading to a reduction in clutter: clutter can distract. Appropriate lighting, plants, an ergonomic set up, and proper equipment, are all things to invest in. Not all these things must be tackled at once, as they can be time-consuming or costly, but in the long run they lead to working from home comfortably.

Sometimes working from home is not an option. If this is the case for you, co-working spaces may be available to rent in your area. This might be an idea to explore and utilize if you find yourself feeling isolated working at home all the time. It could be a break from your routine that will allow you to reenergize, and possibly open up networking opportunities.


This content speaks to general trends found in research literature. It should not replace careful consideration of individual career situations, nor can they take the place of consultation with mental health professionals. 


This document is an extract from the report Resources for Mid-Life Career Changers: Final Report and Web Content, for a research collaboration between the Indexing Society of Canada/Société canadienne d’indexation (ISC/SCI) and the King’s University (TKU) in Edmonton. Supervised, honors-equivalent psychology students conducted the research in partnership with the ISC/SCI as a capstone senior research project in their senior seminar. The ISC/SCI Executive committee collaborated with the King’s Community Engaged Research (CER) Program to initiate and design the project. 

The CER Program at the King’s University facilitates university-community partnerships in which student-supervisor teams engage community partners in the design and implementation of research that addresses community-defined needs. For more information, please contact the Program Manager, Dr. Elim Ng (


Burcharth, A., Smith, P., & Frederiksen, L. (2022). Rehearsing entrepreneurship: Identity formation in the transition to entrepreneurship after an emotional job loss. International Journal of Entrepreneurial Behaviour & Research, 28(7), 1653–1678.

Clayton, L.  (2022, January 21). Home office productivity tips – 13 ways to work effectively from home. Homesandgardens.Com.

Gruman, G. (2020, September 24). How to set up a WFH ‘office’ for the long term. Computerworld.

Haynie, J. M., & Shepherd, D. (2010). Toward a theory of discontinuous career transition: Investigating career transitions necessitated by traumatic life events. Journal of Applied Psychology, 96(3), 501–524.

Hershey, D. A., van Dalen, H. P., Conen, W., & Henkens, K. (2017). Are “Voluntary” Self-Employed Better Prepared for Retirement Than “Forced” Self-Employed? Work, Aging and Retirement, 3(3), 243–256.

How to Create a Productive Work Environment at Home in 2023— (2021, June 7).

Patty, A. (2016, May 4). Being a “mumpreneur” is an option of last resort for most mums. The Sydney Morning Herald.

Robinson, L., & Smith, M. (2022, December 12). Adjusting to Retirement. Helpguide.Org.

Schwartz, A. (2021, January 13). You Are NOT Ready to Retire Until You Can Answer These 7 Questions. Kiplinger.Com. Segal, J., & Robinson, L. (2022, December 5). Volunteering and its Surprising Benefits. Helpguide.Org.

Return to Midlife Career Transition home page