Planning Your Retirement? You May Need to Think Like an Entrepreneur
Updated: Oct 2
After 30 or 40 years as an employee, a midlife career change can require a surprisingly different set of skills.
For much of a successful professional career, the rules of working life are relatively clear.
You have a role. An organisation employs you. There is a salary, a job description, colleagues and perhaps a team to manage. Work arrives in your inbox. Meetings appear in your diary. Someone, somewhere, has decided that your skills are needed.
Then, as you begin thinking about your next chapter after a long career, something changes.
Perhaps you are leaving a partnership or senior corporate role. Perhaps redundancy arrived earlier than expected. Perhaps you have simply decided that you no longer want another full-time executive position.
You may still want stimulating work, income, purpose and professional involvement — but you don’t necessarily want more of the same and you don’t want retirement in the ‘traditional’ sense of the word.
After spending 30 or 40 years being an employee, you may suddenly need to learn how to think a little more like an entrepreneur.
More people are working longer and differently later in life.
The transition from employee to a more independent way of working is already an important part of longer working lives. We can already see this in the UK labour market.
Government figures published just last week show that around 17.1% of employed people aged 50–64 are self-employed, compared with 13.1% of those aged 35–49. Other government research into later-life working patterns found that self-employment becomes even more common among those who continue working beyond traditional retirement ages. Among working 65–69-year-olds surveyed, 37% were self-employed. It makes sense.
New Networks New Knowledge, New Skills
A 'next chapter' of self-employment or a hybrid, will require new knowledge, new skills and new networks. I have experienced all this in establishing StayCurious Coaching
Career change after 50 doesn’t necessarily mean starting a business. It means thinking like an entrepreneur. Outside the corporate world you’re going to need to develop the creative mindset of an entrepreneur. The ability to spot opportunities. The application of lateral thinking. The willingness to learn new skills. The ability to leverage the power of networks. The ability to run a one man business. The ability to leverage your accumulated skills and experience.
From being given work to creating work
As an employee, your organisation created much of the infrastructure around your professional life. It provided the brand, clients, systems, colleagues and opportunities. And a guaranteed salary.
In a new portfolio career or self-employed role, all of that responsibility moves to you:
You have to be able to explain clearly what benefit you offer.
You have to identify people or organisations who might value it.
You have be present where potential customers are found
You then have to run multiple client relationships (with attached admin)
All this can feel surprisingly new and different. Despite your age and experience.
During your corporate career you confidently negotiated multimillion-pound contracts. Today it might feel awkward to say:
“This is what I can help you with — and this is what I charge.”
That isn’t a lack of confidence or capability. It’s simply a new skill to practice.
Five entrepreneurial skills for your next chapter
So what might someone who has spent their whole career as an employee need to learn?
1. Explaining your value without your job title
“I was a partner at…” or “I was Marketing Director of…” explains where you worked.
It doesn’t necessarily explain what somebody should hire you to do now.
A useful next-chapter question is therefore:
What problems am I particularly good at helping other people solve?
Turning experience into a clearly articulated proposition is often the first entrepreneurial step.
Remember to ensure that your LinkedIn profile reflects this forward-looking approach.
2. Building a new network
Long careers can produce large networks — but sometimes surprisingly narrow ones.
Your contacts may mostly work in the same profession, industry or organisations that you do. If you want to do something different you need a new network.
As I have mentioned in previous posts, Herminia Ibarra, Professor of Organisational Behaviour at London Business School and author of Working Identity, has long argued that successful career transitions involve experimenting with new activities and developing new networks. Her work suggests we often discover possible future identities through action rather than thinking our way towards a perfect answer.That makes meeting people outside your normal professional world particularly important.Your next opportunity may arrive through a relatively new relationship rather than someone you have known for 25 years.
3. Becoming comfortable with experimentation
This is another recommendation from Herminia Ibarra:
Corporate careers often reward certainty whereas entrepreneurial careers require a greater tolerance for ambiguity.Rather than deciding, “I am going to become a consultant”, you might run three small experiments:
· Help a former colleague with a project.
· Explore an advisory role with a small business.
· Try some paid mentoring.
One may lead nowhere. Another may reveal something you had never considered.This is very different from writing a five-year career plan — and for someone accustomed to senior organisational life, that uncertainty can take some getting used to.
4. Learning to create opportunities
Jobs are advertised.
Many portfolio-career opportunities aren’t.
Advisory positions, consultancy projects, introductions to founders and non-executive roles often emerge from conversations.
That means networking becomes less about asking, “Do you know of any jobs?”
And more about being curious. (of course!):
· “What challenges are businesses like yours facing?”
· “Where might my experience be useful?”
· “Who else do you think I should talk to?”
This is entrepreneurial behaviour even if you never think of yourself as an entrepreneur.
5. Getting comfortable with self-promotion
For many experienced professionals, this may be the hardest change of all.
Inside an organisation, reputation develops around you. Colleagues know what you have done. Outside it, people don’t.
You may therefore need to become more comfortable talking about your experience, writing about your expertise, reconnecting with people and making your value visible. This doesn’t require becoming a relentless salesperson on LinkedIn.
But it may require accepting that if people don’t know what you are interested in doing, they are unlikely to think of you when an opportunity appears.
Your experience may be more valuable than you think
There is an encouraging side to all this.
Beginning a career transition at 55 or 60 is not starting from scratch.
You may have decades of accumulated knowledge, judgement, relationships and pattern recognition. You probably know things that feel entirely ordinary to you precisely because you have been doing them for so long.
The challenge is often not acquiring another qualification. It is learning how to repackage, test and apply what you already know in a different context. And that requires curiosity (of course!)
Don’t make a decision too quickly
One of the temptations when leaving a long career is to replace the certainty of the old job with immediate clarity around the future:
I need another executive role.
I’ll become a consultant.
I’ll get some non-executive directorships.
But a successful career transition in your 50s or 60s may involve spending some time in-between identities- in what psychologists refer to as a liminal state. Experimenting, talking to different people, trying small pieces of work. discovering what you enjoy — and what the market values.
You don’t necessarily need to become an entrepreneur as the media use the word,but after a lifetime as an employee, developing a few entrepreneurial muscles will give you far more options for creating a purposeful, stimulating and realistic next chapter.
#Retirement Planning # Next Chapter #Career Transition #StayCurious
