• Steve Gilroy

Portfolio Careers for Executives

As part of my role as CEO of Vistage, I meet many senior executives who have decided to leave the corporate career world and move into what is known as a ‘portfolio career’. It’s a growing trend. Older executives, the baby boomer generation, are reaching retirement age in better health and with more financial security than at any time in the past. A healthy 60 year old man can look forward to 20 to 25 more years of useful and constructive life, a woman, even more.[i]

Some have recently sold their company, some have reached retirement age, or been made redundant. Maybe they want to take life a little easier and yet enjoy the challenge and contribution they experienced during their working life. While their reasons for making the change vary, the end goal tends to be the same – to leverage what they know/can do, while taking control of their life and working to their own schedule/plan.

Is this you? If so, the following might offer you some guidance…

Enter the Portfolio Career.

The portfolio career is a term ascribed to Charles Handy in the 1990s, it’s when a person has a number of different occupations for different organisations at the same time – a portfolio of part-time roles.

There are a multitude of options available to you and the main ones considered by most semi-retired executives include:

  • Non-executive directorships (NEDs)

  • Consultancy

  • Interim Manager/Director

  • Angel investor

  • Work within the charitable sector

  • Coaching

Non-executive directorship (NED)

A Non-executive Director basically has a place on the board of a company in the role of ‘critical friend’. Someone to challenge assumptions and critique systems, processes and decisions, the role also calls for strategic input where you can bring your skills and experience to the boardroom discussions. This can be extremely satisfying, however, unlike being a CEO your voice won’t carry any extra weight and you may find yourself frustrated by being overruled at every turn, or by the unwillingness of the rest of the board to actually take decisions at all.

According to the Institute of Directors’ report on The Role of the Non-executive Director[ii], there is no legal distinction between executive and non-executive directors. As a Non-executive Director you will have the same legal duties, responsibilities and potential liabilities as the executive Directors. Consequently there is a risk attached to taking an NED role and before taking up a position you need to satisfy yourself that the financial information is correct and that there are adequate controls and robust systems for risk management in place.

Tim Stevenson, former chairman of Morgan Crucible and Travis Perkins suggests you should be patient before accepting the first NED offer you receive. Make sure it’s right for you before jumping in and committing yourself.[iii]

Several questions to ask before accepting an NED role:

  • Are you fully aware of the legal and governance responsibilities of an NED?

  • Do you have the time to do the role justice? How much time will be involved in board meetings, preparation and follow up from those meetings?

  • What are the financial implications? How much will you be paid and how does that fit with your other sources of income?

  • Are your skills and experience a good match for this organisation?

  • Are the aims and objectives of the company in line with your values?

If you’d like to look into filling an NED role you can find openings and more information through The NED Exchange ( or Non Executive Directors (

Consultancy or Freelance Troubleshooting

Textile production manager working inside factory

The consultant is someone who goes into organisations that are struggling in some area and observes their systems and processes, identifies where the problems originate and offers potential solutions (or maybe they just want to explore some new opportunities or techniques).

Drawing on your own experiences as a senior executive you will have encountered and solved many of the kind of problems facing your clients. However, if you’ve spent the whole of your working career at a big blue chip organisation your experience and skills may not be so relevant to clients outside your original company or sector. Even if they are, selling them to people who don’t know you, or who can’t vouch for your value is a whole new world.

One of the biggest challenges to taking on a consultancy role is that you’ll be self employed and responsible for finding clients. The work itself is generally not the issue – it’s how you find and win new clients.

Before choosing consultancy as an option consider these questions:

  • What sort of a network do you have? This is the first place to go looking for clients and referrals to clients.

  • Are you able to market and sell yourself? Do you have the requisite skills or can you outsource the marketing and sales?

  • Do you know where to look for potential clients?

  • Do you know how to approach potential clients with a proposition that will appeal to them and be financially rewarding for you?

  • Can your prospective clients afford you?

  • Can you survive if you don’t have a steady stream of new clients?

  • Is your input likely to be dated or have you kept up with trends and technology?

If you feel that consultancy is for you then do your research, find useful networking opportunities and consider joining consultant groups.

Useful articles include:

Interim Manager/Director

If you want to hold the kind of senior executive role you’ve held in the past then your best bet is probably to approach executive recruitment agencies. While you may only be looking for a short-term role as an interim director, you may still encounter ageism and scepticism.

A good CV highlighting your skills and experience is an absolute must for these roles as is a good Linkedin profile. And using your network through Linkedin you may be able to find suitable opportunities before the agencies are notified giving you a head start.

Angel Investor

Are you a Dragon? Do you have funds and want to invest in someone else’s business and help them to grow so that you can benefit from the increased profits?

To be an angel investor you will obviously need a significant amount of capital to make the investment. You will also need to have the skills, knowledge and connections that will be useful to the company you’re interested in investing in.

Things you need to consider before committing yourself to an investment opportunity:

  • Are the management team good enough to build the business significantly?

  • Is the product or service really viable?

  • Are the projections and aspirations realistic or fanciful?

  • Do you have the knowledge, skills and/or contacts in that sector or niche?

  • Can you make the return you want to within the time frame you want?

  • Do you have a rapport with the business owners – it won’t work if you don’t get along or they won’t listen to you.

  • Do you have the time and the inclination to be involved on a day-to-day basis?

  • Would you rather just give them the money and let them manage it? This is obviously a much greater risk and doesn’t provide the occupation or involvement you might prefer.

Starting out as an Angel obviously needs some serious research as to how you do it and what the risks and best practices are. Some organisations offering advice and opportunities include:

Voluntary sector involvement

This could be anything from helping out at a local charity shop, running a children’s football league, or serving on the board of a major charity. It may or may not be a paid role.

Before considering working for a charity there are a number of considerations:

  • Do you have any preferred charities as a result of your own personal history or previous involvement?

  • How much of your time will be involved?

  • Do you have the skills and knowledge to make a real difference?

  • What are the financial implications?

  • Could there be travel opportunities – and do you want that?

Your local council may have a directory of opportunities in your area or there are several national websites where you can find voluntary opportunities. When you find a role that appeals contact the organisation concerned and do your due diligence.

Executive coaching

This role is one of coaching top-level executives to achieve their goals and manage their life/work balance so they are effective in the business without burning out. You may have experienced coaching yourself during your own executive days and know first hand how valuable it can be.

Executive coaching qualifications will give you the skills needed to coach effectively, drawing the best out of your clients rather than advising them as you would as a consultant.

As with consultancy, as an executive coach you would be self-employed or running a one-man business and you would have to market yourself and sell yourself to your prospects.

There are any number of coach training organisations including:

If you have a passion for helping others grow and develop then one way into the coaching world is as a Vistage Chair. With Vistage you receive world-class training plus additional tools to set up and run your own Vistage group as a coach and mentor to your members. You also benefit from being part of a community of coaches, with a back-office support. So you run your own business, but within a proven support framework.

For more information contact Vistage on 01489 770 200 or visit to register your interest.


Whichever way you create your own portfolio career, whatever shape it ends up being, your network of contacts will prove invaluable. Many executives are exploring this new path, so you won’t be alone!

If you’d like to explore the area further, and meet others who are also embarking on the ‘portfolio journey’ you could consider joining the Pluralists Club ( and its sub-interest group, the Pluralists Investor Club ( The Pluralists Club was established to help people launch and grow a portfolio career.


[i] [ii] [iii]

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