Self-Employment: What Stays the Same When Change is All Around Us

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Self-Employment: What Stays the Same When Change is All Around Us

Sep 22, 2023

The appeal of self-employment is being taken seriously by companies around the world. Post-pandemic hybrid work models are enabling longer-term work from home. Digital nomad visas in 20+ countries facilitate work from anywhere. Internal talent marketplaces are giving employees more flexibility and choice in what they do and what they learn – even as artificial intelligence is automating tasks and creating content with growing potential to replace the work that some freelancers do. Employment-related change is at a fever pitch.

While there is inestimable value in working for a great purpose-driven company that truly values your abilities and provides a steady paycheck and good benefits, the majority of jobs working for others are no match for the many rewards of successful self-employment. But what is “successful?” Ironically, though we’re surrounded by change, self-employment success factors 10 or 20 years out are likely to stay much the same as they are today.

A Stable Outlook for Self-Employment Success Factors

We all have our own definition of success, with some variations of a formula comprising financial rewards, honoring a passion, intellectual stimulation, and emotional and psychological well-being from personal achievement and the joy found in the work itself. However you define it, four success factors that were operative yesterday will still be operative tomorrow, and beyond: (1) knowing your “why,” (2) clarity on, and alignment with, drivers of satisfaction, (3) fitness for the work and lifestyle, and (4) ongoing attention to burnout prevention. Each are briefly explained below.

Knowing Your “Why”

The real truth about why each of us seeks independent work is not always easily accessible. For some, it’s money. For some, it’s control. For some, it’s ego gratification. For many others who tend to be most successful, it’s passion and meaning. Sure, it can be a combination of all those things, but aligning your work with your values, with purpose, and/or with a passion will never go out of style as a success factor. Authenticity is key, in work as in life, to be our best. So staying connected to the why – what it really is that drove you toward self-employment – powers us through our days. That requires deeply confronting whether you were, or are, running toward a vision rather than running away from a soul-sucking job or a boss you hated.

Clarity on Drivers of Satisfaction

If your self-employment journey isn’t going as well as you had hoped, and not just financially, chances are that the work itself – or your approach to it – is out of alignment with your “drivers of satisfaction.” Alignment with these drivers should be periodically self-assessed to diagnose what needs to be different to improve things for you. That requires clarity on what those drivers actually are. When we think about what, for each of us, are the factors that drive how we feel about our work lives, there are usually five to ten drivers that can significantly impact our perceptions and emotions and, ultimately, our effectiveness. Several of those drivers, beyond money, will be abstractions. As examples, factors like “being in control” or “feeling highly valued by clients or customers” can mean many different things and must be unpacked and more clearly defined for clarity on your definition of what it is you’re really after. Control over what? How you work? When you work? Who you work with? And what makes you feel highly valued? How much you’re paid? Effusive thanks? How much repeat business? How many referrals? When you drill down on each abstract driver to make it more concrete and specific to you, it’s easier to isolate the gaps between how things are and how you would like them to be. Then those gaps can be addressed with an action plan.

Fitness for The Work and Lifestyle 

Successful self-employment requires great self-knowledge, and brutal honestly in assessing your strengths, weaknesses and anxieties. If things could be going better for you, it may not be because of misalignment with drivers of satisfaction, but rather due to misalignment between who you really are and the unique demands of self-employment. There is no shame in deeply confronting whether you’re a good fit for the volatility of independent work and its potential for chronic financial insecurity, the loneliness of being the boss (even if only the boss of yourself), the social isolation if you’re an extrovert, or the impacts on your family. It’s simply not for everyone. That said, those of us who keep doing it know that it’s all worth it.

Ongoing Attention to Burnout Prevention

When it’s all on you as your own boss, it’s easy for self-employment to become the ultimate burnout trap – unless you take precautions. Countless highly capable entrepreneurs with great vision have thrown themselves into work only to flame out early, never to recover. Sustaining independent success for the long haul requires ongoing self-nurturing and, perhaps counter-intuitively, moderation. A powerful self-nurturing cocktail of habits is part rest, part mindfulness, part consciousness and part gratitude. Rest, because self-employment is a marathon, not a sprint, and research clearly shows that productivity unravels without adequate rest. Mindfulness, because stillness or meditation or long walks allow us to be present in the moment, reduce worry, and refresh and restore our capacities. Consciousness, because even a one-person business can derive enormous energy from being purpose-driven for the greater good. Gratitude, because self-employment is a privilege that the majority of people in Western society never experience as a career (even though a recent Dartmouth College study found that 70 percent of full-time employeds would rather be working for themselves). And the science shows that gratitude practice reduces stress, boosts optimism and increases sleep quality.

Antidote to Unpredictability

The world of work has become ever more dynamic and turbulent. But there is stillness in the eye of a hurricane, and these self-employment success factors are pillars of constancy within the maelstrom of change.

Meet The Author:


Steven Cristol

Steven Cristol is a business strategy consultant, career coach, and author of three business books that have been translated into 11 languages. His most recent book, NO BOSS!, is a guide to self-employment success. He was recently the guest interview on Forbes’ Futures in Focus podcast, which can be found here, discussing self-employment trends and the evolving career landscape.


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