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Career Choices

Supporting Director-level Independents

Introduction to the section

The Career Crossroads – Making ‘Best-Fit’ Decisions

The way you approach this key topic will depend on a number of ‘stage and state’ factors and influencers in your life:

  • Personal
  • Family and friends
  • Work / career and use of time
  • Finance needs and wants

These lifestyle and aspirational factors are unique to you, no-one-size shoe fits everyone.

Working Free recognises this and, at this point, we make three assumptions:

  1. That you have got to a point where working for someone else is not necessarily what you want to do and that thinking this through to make a best-fit decision is very much on your mind.
  2. That you may not have made a final decision but you have got to a point where going Independent is a serious option and you want to know more.
  3. That you would find it useful to make your decision within a framework that enables you to do ‘diligence’ on yourself and appraise / review your lifestyle requirements.

Overview & Key Points from the Technical Topic Partner

Chris Dunn of The TDA Transitions & Learning Organisation Ltd has been advising senior business people on career transition matters for over 30 years.

  • Chris Dunn
    Chris Dunn
    TDA Transitions & Learning Organisation Ltd
Contributor Material

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If you would like to make a comment that others can read, see where marked TTC at the end of every Section.  This where you can make your Contributor comment – which is emailed to [email protected]  - and published after screening. Please include your name and contact details so that other readers can get back to you.  The real value in this Section– for all Readers – will doubtless come from learning from other Independents’  experiences and knowledge – what works and what does not work – things to do and things to avoid.

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Overview, Key Points, and Content from the Technical Topic Partner

With the above in mind, we have organised the content of Section 3 as follows:

Some context for your decision-making:

  • Taking ‘Informed’ Control: Vote and Back Yourself!
  • Is Going Independent a Choice?

Making Personal Decisions: A route map to navigate your career choices, whatever you may decide.

  • Where am I? (Evaluating your current circumstances)
  • Who am I? (Personal diligence – assessing yourself)
  • Personal Goals (Aspirations – How I want the future to be)
  • Exploring Options (What seems to fit best?)
  • Action Planning (Setting targets and plans)
  • Continuous Review (tracking and reshaping progress)

We provide some general tips on each of these headings which you can customise in the light of your needs and background.  This is simply a ‘Starter-for-10’ and offered in the same way that a business plan blueprint is provided when setting up and making a decision about a business or a project, i.e. Does this make sense? What are the things I need to consider?

The way everything fits together . . . .   

Section 3 is very much a ‘pre-decision’ module where you have the opportunity to step back, to think about yourself and what you want in the future.  Going Independent is just one option.

Section 4 provides a useful overview of the ‘Independent Marketplace’.  We refer to this growing percentage of people who control their own work / lifestyle as ‘Self-Drive Workers’. It would be useful to look at this section now as it gives the context for what going Independent is all about and the types of activities / sectors that people are working in.

Section 5 focuses specifically on Self-Employment and what you will need to reflect on and put in place.  It makes the assumption that going Independent is now a very solid option for you and you want to get going on developing and actioning a firm plan.

Taking ‘Informed’ Control – Vote and Back Yourself!

The Working Free story starts here with you

No matter what your circumstances, we aim to provide you with a personal decision-making framework to:

  1. Help you to assess yourself, and
  2. Help you to assess your personal and professional lifestyle objectives and to bring clarity to your thinking and plans

The emphasis therefore for the balance of this section is about stepping back and making informed decisions and choices about the bigger picture for you – What next?:

  • What do you want to achieve in your life?
  • Can going Independent deliver this?
  • Are other options more suited and attractive to you?

The $64k question is “Is going Independent to be made as an informed choice or is it simply a reaction to a move away from something?  A form of dissatisfaction or from a ‘Why not?’ state of mind, others do it, so why not me?

The reality is that the independent route is fundamentally a lifestyle decision, not just a work one.  It suits some people and not others.

So checking suitability, doing diligence on your own and with as many others as possible, and exposing yourself to the realities of what it is really like before making a firm commitment, is the way to go.  Hence the significance of this ‘pre-decision section’, forearmed is forewarned.

Here are some insights into what it takes to be successful as an Independent.

Make sure you are clear on your strengths, what you have to offer and your value.  You need to understand how to differentiate yourself.

You need to know this because these are the people and their organisations who will buy your professional product. You might think that those outside your market will provide referrals.  Maybe. But never ever as much.

Read all about being a Self Drive Worker elsewhere on this website.  You are positioned in the 47% of the 32m working population in the UK.  Even if you don’t agree with this interpretation, your own answer is bound to be somewhere near. You might think you are in a lonely place; NOT true!

Always remember, you are as good as your last job. Keep yourself refreshed personally with fitness and professionally by taking part in CPD activities to keep on top of your chosen field of work.

Marketing and selling – these two different things are all-pervasive.  You are doing it all the time. Similarly, there is no one section on this website that covers it all. It’s all over and everywhere!

No sales equals no revenue.  So - if winning business is not something you have done in the past, develop your client relationship and influencing skills and learn from every client conversation.  Always remember that people buy from people - so winning respect, credibility, trust and achieving a level of client chemistry always comes before an order.  Be yourself, be authentic and, above all, develop a ‘client mind-set’ which enables you to understand a client’s needs.  Seeing things from the other side of the table always impresses and leads to better quality proposals and solutions.  95% of an Independent’s success is based on understanding what the client brief is all about.  This takes skill and experience and is always work in progress!

Let your friends know what you do and invest in building your network.  Networking is much more than just winning business, it’s also about collaboration, support and building great relationships.

Set yourself up with good advisers – an accountant, lawyer and others you may need.  Choose wisely and choose people who are not just good technically but who want to work in collaboration with you.  Chemistry is everything.

Manage your time wisely – work on priorities, be organised and efficient in the way you run your business, you can then put your focus on being with clients.

Don’t be afraid to ask for support.  “No-one is wiser than all of us!”  You will always have peaks and troughs and it’s good to step back and talk things through with someone you trust.

Having worked with many executives, I have observed those who go on to become Independent and who do well, not just because of their technical and professional skills and knowledge – important as these are – but because of their mind-set, behaviours, self-knowledge and drive to achieve things important to them.  It is their approach that is the key.  In other words:

  • They have done their homework on themselves and what they want to achieve and on their selected market.
  • They have an outlook which is about self-reliance and being proactive, they have typically cultivated a network of good relationships, they talk in a personally accountable fashion, i.e. they know that the ‘buck stops here’. They enjoy the freedom to act, they are willing and able to adapt and learn.  Above all, they are willing to face a level of uncertainty and rejection with a level of resilience as they recognise that risk and reward do not play out evenly and that peaks and troughs are part and parcel of being Independent.

In a nutshell, we are talking about a ‘can do’ attitude where positivity and openness to opportunities  are not just desirables but essentials to be able to handle the ups and downs of life and where the only way to make things happen is by the drive, skill, knowledge and hard work of the Independent.

Choices and Decisions

Making Personal Decisions – A route map to navigate your career choices

Independent versus Dependent Thinking

An interesting spin on these observations comes from Cliff Hakim in his book “So We Are All Self-Employed”.  He writes that “the biggest mistake in life is to think that you work for someone else.”

I think that Hakim has put his finger on the fundamental points of what being Independent is all about as opposed to being dependent.  It is a state of mind.  I.e. those who buy into Hakim’s philosophy understand what self-determination is all about and therefore have a huge attitudinal and behavioural advantage as they know it’s down to them, there is no safety net!

That is not to say that much can’t be learned, it can, and many Independent stories bear this out.  My analogy would be that behaviours are like muscles – if they haven’t been used for some time they will have got weaker but they can, with application and motivation, be strengthened and further developed.

The challenge is to understand strengths and weaknesses and to put in place plans that exploit the former and tackle the latter.  This is applicable regardless of whatever you decide to do.  It is important in all our working lives.  Thinking of yourself as self-employed and the boss of one’s life and work is the key, I believe, to personal and professional development whatever you may decide to do.

Tips and Further Resources

Tips to get you started

Additional Resources

Stepping back is always useful. Just clear the decks of everything else and simply jot down where you are today – an asset/liability check.

Tip – You may find it useful to jot down your ‘audit’ thoughts in a four-box framework using the headings in the Introduction (Personal, Family and Friends, Work and Career, Finance).  Go for headlines – keep it simple.   This will give you a good summary of how you see today and feel about the quality of your life and the circumstances from which you are about to make future decisions.

What do I have to offer? What motivates me?

Self-awareness is the key building block in the whole of this process.  In personal terms, it answers the key questions – What makes me tick? What motivates me?  What do I enjoy the most?  What gives me most satisfaction?

In marketing / professional terms, it helps you to understand and nail what you bring to the party. This section will help you to define this.

However you do this type of work, you can use the outputs to present yourself in a number of ways – your CV, your bio, LinkedIn profile, website etc.  All can be improved by doing this type of personal diligence activity.

Here are a few thoughts on the homework you can do to create a cohesive profile of yourself.


What am I really good at?  What defines me as a person?  What do I enjoy doing?  Where and when do I fit best into a project/company?  What, above all else, do I achieve?

Tip – Choose six / eight past assignments, roles or projects, ones that you feel typify you on your ‘A game’.  Write these up as case studies – the scenario, what you did, results achieved and learning.  The outputs from doing this are immense.  Firstly, you can ‘nail’ your personal and professional offering.  Secondly, the outputs can be used to personalise your CV / bio etc.  Thirdly, and probably the most important, is the fact that as you have worked it through and written it down, it is at the front of your brain!  This is incredibly useful for confidence in selling and building client relationships.

Don’t rush this as the same data can be recycled in many ways.

Tip – One way to consolidate your case study data is to write your own ‘Ideal Role’ advert.  Imagine that you are reading the newspaper or a good friend is telling you about a role opportunity and suggesting that you look at it in more detail.  What would be in it? What ingredients MUST it have?  Think about things like: How would I ideally want to spend my time? What key words best describe the type of role I would love to do? What would motivate me the most and get me up in the morning?  Don’t just think about the ‘What’ (the KPIs) but think also about the ‘How’ (the culture, environment and the way you prefer to behave).

Where do you see yourself in the next five years (time horizon up to you)

“If you don’t know what 10-out-of-10 looks like, how will you know if you have achieved it?”

Tip – using the same 4 x 4 framework offered earlier, jot down your objectives / personal goals.  Make notes, possibly go for around four for each one, then step back and analyse them.

Ranking them can be useful to get a sense of what is really important.  You may also want to start thinking about your personal criteria for saying ‘Yes’ or ‘No’ to opportunities being presented or that you discover.

This is a very useful exercise for directional purposes and you can feed the outputs into your plans.

There is an old expression “Do you get what you want or do you get what other people are prepared to give you?”  This exercise gives you both clarity and confidence to achieve what you want.

Using the outputs from your diligence work, you will now be beginning to get a shape to your decision-making.


  • Jot down the key decision-making criteria for how you want the future to be
  • What are the critical things you must have? Talk them through with a trusted friend / contact
  • Start thinking about / writing a new CV, bio
  • Draw-up your ideal role / project spec so you gain further clarity on what you would be attracted to and would undoubtedly say ‘Yes’ to
  • Review Section 5 of this website to clarify your thoughts on Self-Employment as a viable option for you and your family. What do I want to achieve?  Can this give me what I need?
  • Start browsing and researching websites and materials that look the most interesting
  • Harness your network selectively to follow through on a few key opportunity areas. Talk to contacts doing what you have in mind and possibly spend time with them in their environment or working with them on a project activity.
  • Possibly, as you refine your thinking, hire a researcher to do some very focused and targeted work, i.e. to explore a particular sector or to get details on Search or other professionals who you want to interact with.
  • Attend functions – dinners, conferences, exhibitions, events, to collect further intelligence, network and to generally understand better future routes to market.

The key to this phase is exploring and discovering opportunities via a balance of networking and researching.  Being-in-the-swim is half the battle and so is keeping an open mind.   As they say “The mind is like a parachute, it is best when open!”

Special point and tip:

Keeping on top of your chosen market place, professional trends and relationship changes is sensible in any role but as an Independent it is vital. Networking, keeping up your CPD, researching, keeping in touch with your respected contacts in different fields, thinking about regularly meeting up with colleagues to talk about issues of the day and generally being open to fresh ideas, are all sensible things to do. Not only does it keep you “on the ball” and interesting to talk to on your current assignment/role but very often it can point the way to future opportunities that can bring both revenue rewards and relationship rewards too.

As part of this way of thinking you might like to consider asking a friend or colleague to be your Supporter. Over the years we have given some thought as to what this role is really all about in practice; how it can be set up, what it comprises and what it can deliver.  Accordingly we have scripted The Supporter’s Guide, which you will find at . . . . . .  Technical Topics.  It is written in a conversational and common-sense style on the basis that you give it to a trusted confidant and they act as a ‘lay’ coach.  The aim of this guide is to provide a consistent set of Supporter principles – to encourage, to listen and to probe.

Experience says that the best things are the simple things!  Clearly monitoring the use of time is key, so having a good, water-tight system in place which is geared to your objectives is a good starting point.

Tip – Watching the use of time when working through the transition from working in an office / organisational setting to working from home sounds a simple one but it is not!  One can easily let hours and days go by as other things can disrupt and block momentum.

Getting into a working routine and replacing the structure you used to have with your own is key to making things happen.  We pick up on this later in the Self-Employment section.

Experience also suggests that what gets measured, reviewed and rewarded gets done!

Tip – Just as you would have done in any of your previous roles, create your own ‘score card’ and board agenda (you thought you had got away from those!) so you create a review discipline for yourself.  Invent your own reward / motivation plan so that excellent performance is rewarded in a way that means something to you.

  • Decisions are best thought through within a framework – role / career / lifestyle decisions are no exception to this rule.
  • Self-awareness is the key building block to setting yourself up for the future – whatever decision you decide to take
  • Personal understanding of why you would say ‘Yes’ or ‘No’ to any opportunity lies at the heart of your success. The diligence work suggested enables this as it gets you to define those things that are important to you.
  • If you don’t know what 10-out-of-10 looks like, how can you achieve it! Clarity is everything.

This all sounds simple but can you answer the following questions right now?

  • What are you really good at?
  • What do you want to do in the future above all else?
  • What is your perfect / ideal role or project?
  • What are your goals for the next three / five years?
  • How are you going to describe / present yourself to others?
  • Who are you going to network with and about what?
  • How are you going to keep refreshed and on top of your game?
  • What do you want to achieve through becoming an independent?
  • As an Independent, what would be your perfect client profile?
  • How will you measure and reward your success?
  • What types of work, above all else, would you like to spend your time doing?
  • On what basis are you going to say ‘Yes’ or ‘No’ to any opportunity?
  • What you would like your client relationships to say about you?

If you can answer all of these now to your satisfaction, by all means move on into action and review the other Working Free materials.  If, as well, this has firmed and fired up your commitment to go Independent, Section 5 on Self-Employment is definitely for you as we go into the specifics of what you will need to assess, evaluate and face.

If you can’t answer all the questions, step back, reflect and work through the diligence areas we have identified.  The work that you have done will be invaluable as a foundation to build upon.

“For those wanting to work on the exercises mentioned in outline in the Career Choices section, and therefore requiring more detailed instructions, formats and examples, TDA have put together, especially for those using the Working Free Service, a detailed Career Exercise Pack.  The 4 key exercises, come directly from the TDA Coaching Transitions Service but have been packaged for the first time to be used on a “stand-alone basis”. To obtain these materials, see further details below, please go direct to[email protected].

The exercise pack has been formulated around an imaginary  executive, at a point of career transition and who is facing the question “What Next?” For the sake of the example the executive is in his late 40’s and is currently the HRD of a FTSE 250 but broadly assesses that his next “working chapter” could well be working as an independent in one capacity or another, he therefore very much wants to get his assessments and personal evaluations together so that he can talk them through with both his family and a Supporter. Possibly also with a professional Coach, career transitions specialist. He wants time to think things through before going off and talking in more detail with specialists such as Interim, NED and Consulting professionals and, of course with his network.

The Career Choices TDA Transitions Exercise Pack contains Four Exercises, which are described in a bit more detail below:

This is a great way to summarise your achievements, strengths, where you fit best, what you contribute and, above all, it points you to source content that you can use to update your CV and bio and indeed to use in your business plan.  It is excellent preparation too for interviews, sales and business development meetings.  Clients often say that this exercise brings greater clarity to everything they have been thinking about.

Incredibly powerful and valuable for providing a sense of direction and purpose.  The outputs can feed into personal and business plans.  It includes a supplementary exercise designed to identify potential conflicts that often exist within a ‘basket’ of personal goals.

On what basis do you evaluate and make decisions on either opportunities presented or on ones that you discover?  This exercise helps you to define the criteria that are important to you. Past clients have found this to be an invaluable decision-making tool.

This exercise is designed to act as an ‘integrator’ to pull everything together.  It is primarily in two parts:

  • Part 1 focuses on those things that you want to have more of, less of or would like to add as they are currently missing.
  • Part 2 focuses on your personal characteristics (emotional make-up) and asks you to reflect on any that might not be serving you well. What do you want to leave behind?  What could you change for the better and what would be the prize if you did?

As with all exercises, a format is provided.  Don’t follow it slavishly but adapt, personalise it and make it work for you.

Behaviour profiling service – to assess and measure behaviours

Chris also uses a range of behaviour tools, notably:

  • Enterprise Behaviour Questionnaire – This behaviour profile is ideal for those considering self-employment as the context is that of working in an entrepreneurial environment.  It provides a template of your behavioural preferences and looks at your style and approach to people, events and situations.  It can also reveal tension areas, i.e. those that are likely sources of stress.  From this, you can create a personal action plan – the key behaviours to work on.
  • My Ideal Role Profile – this is a behaviour questionnaire application created by Behaviour Science Systems (BSS). The feedback report clearly identifies those behaviour preferences which make up an individual’s ‘Ideal’ behaviour role spec.  This is useful for whatever decision or direction you take.

Chris is trained in the use of both profiles.  Both fit together well and can be exceptionally helpful to add value to your self-analysis and help to put focus on those behaviours you will need to develop as you tackle the challenges ahead, particularly those relating to marketing and sales, building and maintaining client relationships, spotting opportunities and developing enterprise behaviours.

Managing your Transition to Become an Independent

“All transitions require adjustment and change and this move to become an Independent is no different, so what can we learn from others who have already gone down this career path?

In the course of my work I have been fascinated as to “ Why do some find navigating career transitions easier than others?”

In the article of this title I offer my observations. Please seewww.tdatransitions.co.uk  The article is positioned on the “Creative Outplacement” page of the TDA website. I trust that you find my observations useful.

A great deal of what I have observed relates not just to the acquisition of fresh knowledge, skills and behaviour but to “mindset”, your personal approach to people, life generally and to events.

www.mindsightuk.biz  have developed this theme along very practical lines, “mindset determines how we use our other attributes”

Do You have a Successful Mindset? One that can take you forwards and help you to become the type of Independent that will enable you to flourish? One that will help you  to become the very Best that you can be?

What type of Independent will you be? These types of questions I suggest are sensible to explore as you set out on this important career transition.

Mindsight, amongst other tools/services that they offer, have developed a very useful questionnaire ( the CEQ- Self Efficacy Questionnaire). The CEQ measures 6 elements that their research indicates are key to the successful management of change. It is available, on line at their website, at no charge.

After completing the CEQ, you can obtain a download of your results, together with a very informative action planning workbook.

In Conclusion.

There are many other resources worthy of exploration but I trust that Career Choices, Section 3, has given you a useful “start- up” framework to enable you to think through how to approach your “Next Step”.

The very best of luck, Chris Dunn”

Reading List

There are hundreds of transition, career management and self-development books on the market but here are some classics and some you may wish to explore later:

  • We Are All Self-Employed by Cliff Hakim
  • The 7 Habits of Highly Effective People by Stephen Covey
  • Keys to Personal Development by Stephen Covey
  • Daily Reflections for Highly Effective People by Stephen Covey
  • The Tipping Point – How Little Things Can Make a Big Difference by Malcolm Gladwell
  • Blink – The Power of Thinking Without Thinking by Malcolm Gladwell
  • Outliers – The Story of Success by Malcolm Gladwell
  • Tuesdays with Morrie: An Old Man, A Young Man and Life’s Greatest Lesson by Mitch Albom
  • Who Moved My Cheese? An amazing way to deal with change in your work and in your life by Spencer Johnson
  • What Colour is Your Parachute? A Practical Manual for Job Hunters and Career Changers by Richard N. Bolles
  • Born For This: How to Find the Work You Were Meant to do by Chris Guillebeau
  • Encore Career Handbook: How to Make a Living in the Second Half of Life by Marci Alboher
  • The Celestine Prophecy: An Adventure by James Redfield
  • Whatever Next? by Jeremy Clare

For further information on anything in this section, please contact Chris at [email protected] .

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Chris Dunn
TDA Transitions & Learning Organisation Ltd

Chris Dunn of The TDA Transitions & Learning Organisation Ltd has been advising senior business people on career transition matters for over 30 years.  He has a particular interest in releasing enterprise potential and he coaches, facilitates, consults and teaches in this sphere.

His original Entrepreneur Development Programme enabled 1,700+ executives to make the transition from corporate life into being their own boss.  Chris later applied his enterprise understanding in the franchise sector and worked with some of the biggest brands such as BP Connect, Boots Opticians, Pizza Hut, Costa Coffee and Snap-on Tools.

Chris manages this section of the Working Free website, pointing to what you need to know and where you can get it from.  He has a number of published works to his credit including Who Are Your Best People? (Kotze and Dunn – FT/Prentice Hall) and Starting a Business on a Shoestring (Penguin).  He is also the designer of a range of self-help training and development kits including Making Redundancy Work for You, Self-Marketing: A Guide to Creative Job Search and Business Success through People, a training analysis kit for small businesses.

To accompany his work in this section, Chris can make available chapters from Starting a Business on a Shoestring. He can also provide access to BASIS (Business Attitude Style Information System). This is an enterprise profile which provides insights into behaviour strengths and possible barriers to success for those wishing to set up their own business.  Further details are contained in Additional Resources at the end of this section.

Chris can be contacted at [email protected]www.tdatransitions.co.uk

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