How will you design your future work life after selling your business?

This is the third of our four-part special on exploring your motivations for selling your business – and designing a positive future work life.

So far, we’ve explored your motivations for exiting your business and the challenges of forecasting what will make you happy in the future , as well as tips for achieving this. And there are many more complex factors to consider when selling a business.

Happily, the Melo team is on hand to guide you through this stage of your business journey whenever you’re ready to get started.

The big challenge, as with all financial planning, is that we tend to delay starting the process – in part because we’re unsure about what we’ll do after we sell.

Keep reading to discover some of the key questions to ask yourself if you want to build more certainty about your plans for the future. We’ll also outline some ideas to help you design your future work life.

Even if you know what you’ll do after selling your business, or you don’t plan to continue working, these myth-busting ideas and thought experiments may help you to double-check that your current choice is the right one for you.

There are no golden rules about what’s right for your future

As the well-known miner’s proverb goes, “Those with the gold make all the rules”. Once you have the gold from selling your business, you will make the rules!

In other words, as you no doubt tell your financial planning clients daily, there’s no one-size-fits-all approach to planning for your future.

You need a plan tailored to your specific circumstances, values, and aspirations because each of us is unique in many ways.

For example, psychologists now suggest we have 25 or more facets to our personality alone (more on this below).

Beyond that, you have a unique set of:

• Emotional styles (resilience, outlook, social intuition, self-awareness, sensitivity to context, and ability to maintain attention)
• Attitudes – To every question under the sun, many of which come from our unique life history
• Habits and hobbies
• Fascinations and motivations
• Ideas that make us laugh
• Circumstances – Physical, mental and financial
• Appearance and vocal accents
• Educational attainments and other skills
• Character strengths – Such as courage and resilience
• Talent strengths – For example, problem-solving and leadership
• Values and what we value – check out the previous article in this series for more on this.

We may also have unique roles as family members and friends to people in our social groups and communities.

So, unfortunately, we can’t give you a set of instructions that will tell you exactly how to plan your future. But, we can share some questions that might help you explore how to redesign your work life after exiting your business.

Some of these ideas come from our own experiences, but most draw on the lives and research of experts in career counselling, life design, and psychology.

If you want to find out more, here’s a handy list of awesome reads to get your teeth into.

Here are 12 ideas and questions to help you get started on your life-planning journey.

We’d love to know your thoughts on these – and any others you’d add to this list.

1. Are you focusing on potential obstacles (or visualising your success)?

Most of us want to boost our chances of thriving in life while reducing the risk of crises.

Relatively new research shows that a key to success in achieving any life goal – from losing weight to passing exams or acquiring more clients – is focusing on the obstacles in your way.

The widely shared idea of visualising your future success (rather than the work required) does not tend to deliver good results.

Who knew?

Indeed, the evidence shows that the old “vision boarding” game can make things worse for those who most need help.

We need a better approach to our vital life projects, and psychologist Gabriele Oettingen has found one.

Her four-step, “WOOP”, thinking process encourages you to:

1. Start with a “wish” about what you want to change.
2. Think about the best “outcome”– and how you’ll feel when you achieve it (this is where you get to dream!)
3. Think harder about what “obstacles” could stop you from doing what’s necessary to achieve your intended outcome.
4. Develop “plans” for your actions when those obstacles appear.

The WOOP approach – which also works wonders in a financial planning context by the way – turns traditional positive thinking on its head.

Here, you’re encouraged to look for (rather than avoid) obstacles in your projects, so you’ll know what to do when these obstacles crop up – as they’re sure to do.

Of course, one obstacle might be your lack of expertise in exploring your options around complex questions, such as how to make a sound plan for selling your business – we can help you with this!

You need to feel capable or supported to fully engage with complex challenges. This could help you build what psychologist Albert Bandura calls “self-efficacy” – a belief in your ability to execute tasks successfully.

Without this sense of competence, you might rely too heavily on the slippery asset of motivation. Dr BJ Fogg illustrates this beautifully in his Fogg Behaviour Model, which suggests that ability, prompt, and motivation, must all converge at the same moment for a behaviour to occur. If you don’t take a certain action, it’s likely that at least one of these elements is missing.

So, keep the WOOP process in mind as you review your business and life plans, and continually ask yourself, “What are the obstacles to progress?”

This may all sound obvious, but the evidence set out in Oettingen’s book shows how powerful this approach can be.

We (and our clients) make much more progress when, after dreaming about completed goals, we immediately think hard about the obstacles to our progress and how we could overcome them.

2. Are you embracing your curiosity and re-framing questions?

Experts suggest there are broadly two types of design problems:

1. “Tame” problems – Where outcomes are predictable and repeatable.
2. “Wicked” problems – Where the inputs and outcomes are far more unpredictable.

Designing a new machine or reconciling the numbers in your accounts is complex and gruelling work. But those challenges are tame compared to the wicked problem of satisfying your ever-changing human needs.

Too often, we assume a problem has only one solution—the first one that comes to mind. It’s only natural, as our brain is an energy-saving device.

According to the Nobel prize-winning psychologist Daniel Kahneman, your brain prefers to “think fast, not slow”. It’s human nature to grab for quick and simple answers even when you know the problem is hugely complex.

For example, when you want to escape from the tedious tasks associated with your work, you might assume the solution is to leave your job altogether.

It might not always occur to you to step back and reframe this question. Instead, you could ask yourself, “How could I remove some of the mundane tasks from my work, so I can focus on the jobs I enjoy the most?”.

At Melo, we can help you streamline your processes so that you can focus all your energies on preparing your business for sale.

3. Can you see your assumptions?

The pressure of work and our desire for quick answers also means we’re sometimes not as objective or open-minded as we’d like to be.

Occasionally, you might hold on to a flawed belief about an idea, person, group or institution. And confirmation bias – which many psychologists describe as the mother of all behavioural biases – may prevent you from seeing your flawed assumptions.

As a result of this bias, you’re likely to instinctively favour information that reinforces your existing beliefs and ignore or dismiss ideas that contradict them.

It’s also human nature to opt for quick answers (“common sense” maxims) for guidance when faced with complex life challenges, such as planning your future work life.

Unfortunately, relying on common sense answers can create all sorts of problems.

As Albert Einstein said, “Common sense is just the collection of prejudices we acquire by age eighteen.”

Daniel Kahneman was also critical of common sense. In his book, Thinking Fast and Slow, Kahneman describes common sense as being more about judging than thinking.

We make snap judgments of ideas based on whether they agree or disagree with our current beliefs (confirmation bias).

The hard truth is that common-sense maxims can’t help us with complex problems about life, love, or work. In fact, as these examples show, common sense can often send conflicting messages about the best course of action.

So, we all carry the odd unhelpful belief that leads us to make poor assumptions – like the perfectly natural belief that we can forecast what will make us happy – as outlined in the previous article.

We also acquire misleading beliefs from popular culture.

In relation to planning your work life, one of the most popular beliefs is that you should always follow your passion. The only problem is that there’s no evidence to support this common-sense assumption.

Professor Cal Newport has written a book and delivered a popular TED Talk on this subject. He says the “follow your passion” idea only got embedded into our Western world psyche 20 years ago.

It started when a video clip of Steve Jobs telling graduates to follow their passion went viral online.

Ironically, Steve Jobs did not start with a passion for his work – his biographers say Apple was something he stumbled into. Jobs only found his passion for computers after he became more skilled and successful.

Studies show that very few people have a passion relevant to their career choice.

And there’s no evidence that matching a personal interest to an occupation leads to happiness.

Passion grows as you get better at your work and your job satisfaction is more closely related to intrinsic motivators – which we’ll look at now.

Of course, your passions may inform the kinds of projects you want to support – whether financially or through your efforts.

However, a passion for a particular activity or cause doesn’t tell you what type of work (or working environment) you might enjoy in the future. These are quite different questions.

4. Are you considering your intrinsic motivators?

You’ve probably spent most of your working life being driven by external motivators – factors outside of yourself that drive you to achieve.

Think about it.

You study for good exam grades and work to generate pay cheques, in part to grow your income or keep others happy. You might also complete many tasks to avoid reprimands from your boss, regulators, or your partner.

Such extrinsic motivators can help you achieve your short-term goals. But, on their own, they don’t usually offer much long-term joy or personal growth.

On the other hand, intrinsic motivators give us personal satisfaction and a sense of fulfilment – so they’re more sustaining.

The theory suggests we all have (to varying degrees) three intrinsic motivators:

• Autonomy – Desire for control over your actions, including freedom of speech.

In the work context, this means having an appropriate level of freedom to choose how you solve problems. Unsurprisingly, this freedom tends to boost creativity.

• Mastery – Ambition to become skilled, which drives your commitment to learning and development.
• Purpose – Wanting to do work that contributes to something more than your own needs and adds real value to the world. You’re likely to be more motivated by work that aligns with what you value and your professional goals.

If you can find or redesign a work life that incorporates these three intrinsic motivators, you’ll probably feel more engaged and enthusiastic. This in turn could make you more resilient to the challenges of your next work-life transition.

5. What does IDEAL work mean to you?

No assessment of an ideal work life is complete without this Venn diagram.

Popular among life coaches, this diagram suggests that it’s worth pursuing work that:

• You love
• You’re good at
• You can be paid for
• Provides a service the world needs.

It’s a neat diagram and a wonderful ambition for sure, but it’s hard to score well in those four circles consistently.

And, as we’ve seen, you’re unlikely to know if you’ll love a new role without trying it – and getting good at it.

So, be kind to yourself when you’re not in that central zone. In the real world, that will be much of the time.

Also, be aware that this diagram is often misleadingly used to describe the Japanese concept of Ikigai (which means “a reason for being”).

However, Ikigai is a very different and easier state to reach. In short, it involves:

• Starting small
• Releasing yourself
• Harmony and sustainability
• Finding joy in little things – rather than setting impossibly hard goals
• Paying attention to the here and now.

All of which have been proven to be drivers of happiness.

So, be careful with this Venn diagram. It illustrates an ideal and doesn’t apply to those who have made (or will make) enough money to:

• Undertake unpaid work for a charitable cause
• Do unpaid work for a fixed period to acquire a new set of skills or complete a project, such as writing a book.

6. Have you reviewed the skills you need for your future work life?

If you’re exploring a completely new work-life direction after selling your business, then books like What Colour is Your Parachute by Richard N. Bolles or How to Get a Job You Love, by John Lees are worth a read.

John Lees, one of the UK’s most respected career counsellors, identifies five skill categories to help us explore our work strengths:

• People skills – Interpersonal abilities, such as communication, compassion, and teamwork
• Information skills – Gathering, analysing, and using information effectively
• Skills with things – Practical skills involving equipment, tools, or physical tasks
• Enterprise skills – Leadership and project initiation, direction and management
• Concepts and ideas – Skills related to creativity, strategic thinking, and problem-solving.

Bolles’s book includes the famous “flower petal exercise” – another self-assessment tool designed to help you identify your career objectives and life goals.

Painting the flower picture might help you reflect on your personal needs from work, such as:

• The values and skills of the people you enjoy working with
• A firm’s size and culture
• Working conditions, hours, and organisational structure
• Transferable skills you can apply – and acquire
• Specific knowledge areas that interest you
• Your desire for leadership responsibility
• Income and other benefits.

These books (and John Lees’ skill card set) could provide valuable practical guidance when you’re navigating a work-life transition.

More importantly, these resources could provide the opportunity for you to explore your motivated skills – the type of work that gives you the most satisfaction.

This self-awareness is crucial whether you’re exploring a future of employed work or one where you design a new business.

This may also be a great way to uncover any further training or coaching needs.

7. How well do you know yourself?

There are various personality self-assessment tools available, but we suggest you explore one based on the OCEAN model of personality.

OCEAN is a mnemonic for remembering the traits of:

• Openness
• Conscientiousness
• Extraversion
• Agreeableness
• Neuroticism (a tendency towards emotional instability).

Professional psychologists recognise the OCEAN model as valid because it’s backed by extensive research, offers a more detailed assessment of our personality, and measures traits on a continuum. Unlike the Myers-Briggs Type Indicator (MBTI) questionnaire for example, which ignores any spectrum of differences.

Various teams of psychologists have developed expanded versions of this OCEAN (aka the “Big Five”) assessment to offer deeper insights into our personalities.

For example, the HEXACO Personality Inventory (HEXACO PI) includes a sixth dimension of honesty and humility.

The HEXACO model expands on the OCEAN model.

Psychologists swapped the “E” for an “X” (eXtraversion) and replaced the “N” for “Neuroticism” with an “E” for “Emotionality” because that word is more readily understood.

The HEXACO model unpacks each of the six main traits into four facets, as shown here:

• Honesty-Humility – Sincerity, fairness, greed-avoidance, and modesty
• Emotionality – Fearfulness, anxiety, dependence, and sentimentality
• Extraversion – Social self-esteem, social boldness, sociability and liveliness
• Agreeableness – Forgivingness, gentleness, flexibility, and patience
• Conscientiousness – Organisation, diligence, perfectionism, and prudence
• Openness to experience – Aesthetic appreciation, inquisitiveness, creativity, unconventionality.

The model also includes “altruism” as a standalone facet, giving it a 25-point scale.

You can take the HEXACO PI here for free.

Let’s take an example participant, Sam. The graph below shows Sam’s scores (the green line) compared to the median of those who took this assessment.

As you can see, Sam is highly “socially bold” and displays less “gentleness” compared to the average participant. Being aware of these tendencies could help Sam improve their communication with others.

If you’d like to explore this assessment tool further, check out the scale descriptions of the HEXACO personality inventory.

Remember that these self-assessment tools are designed to help you understand yourself – there’s no need to tell anyone else your scores.

That said, it can be enormous fun to share these insights with trusted friends and family members. It could also help you build bonds of mutual understanding.

Most importantly, be aware that there are no “good” or “bad” test scores.

The value of completing these assessments is in seeing how you differ from others (and from the “average” person) on these facets of personality.

Your scores can also offer valuable insights into the type of work and environments in which you might thrive.

For example, someone like Sam, who has a low score on the “sociability” trait, may not thrive in highly social environments, such as open offices.

Conversely, you may do better in such offices if you have a high “sociability” score.

Just be aware that simpler (binary output) personality models like the MBTI – which, for example, label us as either extroverts or introverts – are typically less helpful.

This is because they lack the detailed insights provided by more sophisticated models such as HEXACO (which provides scores on a scale for each personality trait).

Personality is rarely black and white. In fact, it’s estimated that around half of all people switch between introverted and extroverted states depending on the situation. These are “ambiverts”.

Research shows that individuals who fall into this category often have a significant advantage in sales roles. Read this research by professor Adam Grant, a specialist in organisational psychology, to learn more about this.

Grant’s findings could provide extremely useful insights for crafting your recruitment strategy too.

8. Have you identified what your personal needs are for your future work life?

Our suitability for future work roles is one thing.

Your motivated skills and intrinsic motivators are quite another – so it’s vital to consider these in your plan.

It may also help to highlight the gaps between what you believe you need from work and what you have now.

And the Melo team is on hand if you need a little guidance. Our “Exit Readiness Assessment” and “Business Effectiveness Review” can help you identify sales readiness and business process gaps.

We’ll show you how to zone in on the right buyer and secure terms that are right for you, your team, and your clients.

What’s more, you can take a similar (gap analysis) approach to assess your personal needs from any work you might do in the future.

A personally focused exercise may also help you prioritise business process improvements that will make your work life easier in the short term.

In the next (and final) article in this series, we’ll outline this work-needs assessment tool.

9. Are you exploring multiple options for your future?

Another assumption that’s best avoided (highlighted in Designing Your Life by Bill Burnett and Dave Evans) is that there’s only one best version of you.

Physicists might argue about whether we live in one of many parallel universes, but without a doubt, there are many possible career paths you can follow.

Moreover, you could add value and find happiness in any route you choose. So, it’s best not to get too hung up on finding the one ideal version of your future – you can perfect your work life as you go.

You just need to find intrinsically motivating work that meets most of your needs, most of the time.

That said, research by Professor Daniel L Schwartz at Stanford University, also suggests that you can benefit enormously from starting your new work-life exploration with three ideas rather than one.

It turns out that having several possible roads to travel results in more – and better – final solutions.

If you start with just one idea, you might be tempted to refine it over and over again. This could mean that you miss out on potential innovations.

Instead, try coming up with three viable options. There’s no point in listing a crazy plan B and an impossible plan C, just to make plan A the only one you take seriously.

So, the expert advice is to create the following:

• Plan A – This might be what you already have in mind or are already doing – but with more of the work you enjoy and less of the stuff you don’t!
• Plan B – The work you’d consider if plan A were no longer available – perhaps because of regulatory or technological disruption to your market, such as advances in AI.
• Plan C – This may be more of a wild card. It’s something you’d do if money were no object, which it might not be in the future.

For ideas on plan C, you might want to consider career aspirations you had in the past, which you didn’t pursue for one reason or another.

We love this poem – The Road Not Taken – don’t you?

Are any of those “roads not taken” roles still available and of interest to you, now?

Do you have the knowledge and skills to move directly into one of those roles – or will you need to develop them?

You may not find a specific role in the road not taken exercise, but it may offer clues to what you really want from your future work life.

10. Are you planning to try before you buy?

Ultimately, aside from luck (which contributes significantly to some endeavours), we agree with Da Vinci.

We’re impressed by the urgency of doing things and trying things out.

Career counsellor John Lees seems to agree, pointing out that many successful career transitions are “inside jobs” – where the applicant is already inside or connected to their new employer before the job opens up.

This may happen if you’re working as an experienced intern or are well-known to the firm’s key people.

So, the suggestion, once we’ve listed a few work lives that interest us, is to explore them in one of two ways:

• Networking – Talking to people who are currently doing the roles that appeal to you, which, as noted earlier, also helps you avoid the bad forecasting trap.
• Have a go – Invest some time in the new role or observe others doing it to test your assumptions about what’s involved and whether you’d enjoy it.

11. Could you remove some of the “gravity” problems you’re facing?

While considering all the questions above, you may have encountered one or two “gravity” problems.

These are the things you cannot change – and must work around.

Just remember to re-frame (one of our favourite games!) these gravity problems, to test how stuck you are with them.

Your personality is not a gravity problem. Psychologists do not describe low or high scores on a (sound) personality assessment as strengths or weaknesses.

Introversion, for example, is not a weakness in business and is now more widely understood as a strength. Quieter, more focused people are essential for dealing with complex business challenges. They also tend to stick longer at the deep work necessary to develop outstanding pieces of work.

That’s not to say that extraversion is a disadvantage – it’s certainly not in other regards. This is just an example of a gravity problem assumption worth testing.

Also, findings from Albert Bandura’s research show that people engage more in challenging tasks when they learn more about what’s involved.

So, talking with others who’ve been down the road you’re travelling, is a great way to check if your challenges are more solvable than you think.

The same applies to your financial planning clients, of course.

You’ll have met many clients who assumed their tax challenges were a gravity problem – until they came to you for advice.

So, please test the boundaries of your gravity problems to understand what’s within your control.

12. Are you committed to deciding what you’ll do?

In his book, Happiness by Design, Paul Dolan, professor of Behavioural Science at the London School of Economics, suggests we’re happier when we’re “deciding, designing, and doing”.

Yes, we’ve suggested starting your future work-life exploration with some options – but there are enormous benefits to committing to one of these sooner rather than later.

Research suggests that keeping your options open for too long is generally not a good idea.

Harvard psychologist Dan Gilbert (in Stumbling on Happiness) points to a study in which participants were split into two groups and then asked to choose one painting from a selection to take home and keep.

• One group was told they could later change their minds and swap the painting for another.
• A second group was told they could not change their minds.

The second group reported being happier with their choice.

Once we decide on (or only have) one option, we typically feel more comfortable with what we have.

Unsurprisingly, studies also show that holding onto multiple options undermines our working memory and our ability to focus on other projects as we keep churning over our options.

Some people get caught in an “optionality trap”, habitually collecting options, avoiding decisions, and missing opportunities.

In short, while having choices seems to offer more security, it can lead to paralysis by analysis, which ultimately hinders our progress.

At the heart of all this is the tension between our desire to be free to choose (one of our intrinsic motivators) and the problems that come with too much choice.

You can learn about the wider societal issues related to this in this TED Talk by psychologist Barry Schwartz, author of The Paradox of Choice.

Of course, no work-life choice is forever. Ultimately, your work choices can be changed – if not always reversed.

Our point is that it pays to work hard in the design phase, so you feel comfortable making decisions and following through on them.

Coming up next

In the next and final post in this series, we’ll outline a simple model for assessing the value of your future work-life ideas.

This spreadsheet-based tool will also help you assess the gaps between what you need from work and what you have now.

So, even if you don’t plan to work after selling your business, this exercise might help you focus on business improvements that could make your life easier now.

And don’t forget, our Business Effectiveness Review can help you with that too.

Get in touch

We live in the thick of this challenging market with our business owner clients every day, so we can quickly assess your needs and identify how Melo can help.

To find out more, drop us an e-mail hello@melo.co.uk or call us on 0113 4656 111 for more details.