From Employee to Solopreneur: A Practical Guide to Self-Employment After 50

Are you tired of office politics, rigid schedules, and unfulfilling work? You're not alone. According to Jon Younger, PhD, author of Agile Talent, over a third of the US workforce now freelances, driven by the desire for flexibility, mobility, and pursuing passion projects. With digital platforms connecting skilled professionals globally, self-employment is on the rise.

To succeed on your own requires more than just quitting your job. It demands grit, resilience, and a healthy dose of reality about running a business.

Mindset Shifts for Success

The first step to going solo? Get clear on your motivations.

  • Know your "why" – is it to control your schedule?
  • Make more money?
  • Work on projects you believe in?

If you're driven only by potential income, think again. Feast-or-famine earning cycles mean you must find internal rewards by following curiosity or purpose.

As psychologist, author and filmmaker Meredith Fuller OAM [1] explains,

"Understand your motivations and needs. Work should align with your values and purpose." Examine whether you genuinely need the social connections and structure of office life or if you can find purpose in working for yourself as a consultant."

She further advises:

"Know yourself before taking the leap - independent work isn't for everyone. Be honest about your tolerance for risk and rejection."
Next, shift your mindset around networking. Jon Younger [2] notes that freelancers must have: 
"grit, resilience and be good networkers."

Karen Wickre, [3] author of Taking the Work Out of Networking, explains:

"View networking as 'gardening' - cultivating relationships over time. Avoid networking out of pure necessity."

Instead, connect authentically with people who share your interests. Your network will blossom naturally.

Finally, prepare mentally for uncertainty. Running your own business means sacrificing a steady paycheck. But the autonomy can be thrilling if you have the self-discipline to structure your days. Like a surfer catching the next wave, remain open and alert to new opportunities. As Matt Dowling [4] points out:

"I don't think it's necessarily one type of individual that will thrive as a freelancer, but simply knowing where the pitfalls are, I think, can have a big impact."

On whether you will be able to cope with making a shift to solopreneur, Maya Shankar, PhD, [5] a cognitive scientist, on a recent podcast with the Huberman Podcast, notes we often fear change in light of whom we are today, not realising the future will change us:

"We tend to imagine how our present-day selves will respond to that future change...We forget that significant changes in our lives can profoundly change us."

Starting Strategically

Only quit your job once your consulting business is ready for launch. Begin by moonlighting as a "side-gigger," caution experts to avoid financial pitfalls. Have at least three months of living expenses saved to cover basics during slow periods.

Consider spending a year or two building your portfolio before going solo full-time. Look for ways to apply your hard-won experience to profitable niches. Meredith Fuller suggests first:

"Volunteering or taking on side projects to build experience and credibility."

Acquiring the Skills to Succeed

Learn the business basics – from marketing and pricing to accounting and productivity hacks – before hanging your consultant shingle. Study predecessors in your field who built thriving solo careers. Seek a mentor who can guide you through the rocky patches from their experience.

Outsource specialised tasks to other freelancers so you can devote time to high-value services for clients. Build a support team to handle your weaknesses or things you dislike.

As Meredith Fuller advises,

"Identify skills you already have from unpaid work that could translate to self-employment. Analyse your past behaviors to predict your capabilities."

Nothing happens without clients. Identify a profitable niche using your unique skills, interests, and experience. Get crystal clear on the target customer's pain points so you can tailor solutions.

Promote yourself on social media to demonstrate expertise, but don't count on viral fame. Look for networking events, conferences, and peer groups to connect personally. Research potential client companies and contact key decision-makers directly with tailored pitches highlighting proven value.

Pricing Your Skills Fairly

Valuing your time traps many beginners. Price too low out of desperation, and you signal inferior quality while working unsustainable hours. Price too high without proof of value, and no one will bite.

Aim for win-win relationships with clients who respect your expertise. Consider value-based pricing – what outcomes will your work enable? Have a minimum rate for quality clients and stand firm. As a consultant with specialised skills and deep experience, an hour of your time is worth far more than basic labour costs.

Staying Relevant in a Changing World

Complacency kills in consulting. Make learning a lifelong habit to future-proof your skillset. Follow industry leaders outside your niche for fresh insights. Attend conferences and read voraciously to stay on top of trends.

Consider collaborating with younger freelancers through online marketplaces or local networking groups. Jon Younger suggests:

"...surrounding yourself with younger people to stay relevant and avoid the 'half-life' of your knowledge."

Remain open to unexpected transitions in your consulting business. Sustaining an abundance mindset allows you to explore new directions rather than settling into retirement.

Achieving Sustainability as a Solopreneur

Consistency earns trust with clients. Use freelancing platforms to find projects and cultivate direct relationships and off-platform referrals.

Build a community for support and knowledge sharing. Groups and networks help you weather the pace of change – you're not alone. Educate clients unfamiliar with utilising freelancers to improve collaboration.

Embrace the flexibility to reinvent yourself, letting your network blossom organically. Keep perspective through life's transitions – the lone path often disappears when you walk it. You can build a fulfilling and financially stable consulting career with focus and perseverance.

The Path to Fulfillment

For older professionals seeking more autonomy and purpose, self-employment offers attractive possibilities. But succeeding as a consultant or solopreneur requires far more than domain expertise and qualifications. It demands a shift in mindset plus grit, resilience and business acumen.

By understanding your personality, work style and income needs upfront, you can determine if independent work suits you. Experiment with side projects while employed to build skills and test your tolerance for uncertainty. View networking as relationship gardening, not desperate self-promotion.

With the right mindset and strategic foundation, you can transition successfully from employee to solopreneur. Define your rhythm, determine your future and continue making an impact with your hard-won wisdom. The autonomy of self-employment allows you to follow your purpose while reinventing your career over a lifetime.

Five Takeaways to Get Started on your Solopreneur Journey

  1. Clarify your motivations and temper income expectations
  2. Consider starting as a side-gigger while building your portfolio
  3. Learn business skills like marketing, pricing, productivity
  4. Promote niche expertise tailored to your ideal client's needs
  5. Cultivate relationships – your network is your lifeline


  1.  Meredith Fuller -
  2. Jon Younger -
  3. Karen Wickre -
  4. Matt Dowling,, many of the ideas that inspired this article are from his conversation with me on the Wisepreneurs podcast -
  5. Maya Shankar, PhD How to shape your identity and goals -

Related Reading
Navigating the future of work
Freelancing for the over 50s