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  • Portfolio entrepreneurship – finally a name for the career I have been building for 25 years

    Portfolio entrepreneurship – finally a name for the career I have been building for 25 years

    Management thinker Charles Handy was talking about portfolio careers decades before fractional executive, interim management and the gig economy became the workplace terms they are today.

    Handy envisioned a future in which a person’s career would no longer necessarily consist of one employer, one title and one long climb up the organisational ladder. Instead, expertise would form a portfolio that could be applied across different roles, organisations and stages of life.

    His ideas run through books such as The Age of Paradox and The Second Curve. Handy is also known for the concepts of portfolio career and shamrock organisation – the shamrock organisation. Today, these ideas seem astonishingly relevant.

    When I began exploring Handy’s ideas more closely, I was struck by a realisation: This sounded all too familiar.

    Apparently, I have been building a portfolio career for about 25 years. I just did not know what to call it.

    One employer, one title, one career

    The traditional career model is easy to understand. You join a company. You learn. You progress. You take on more responsibility. Perhaps you change jobs once or twice. Eventually, you rise as high as possible in the organisation and enjoy the security that comes with a long career.

    For many people, it is undoubtedly an excellent model.

    Not for me.

    By nature, I am fast-paced, productive and efficient. I quickly become enthusiastic about new and interesting things – and when I do, they can easily command all my attention and resources. I want to see things happen. Preferably quickly.

    When faced with a difficult problem, my first thought is usually not:

    Oh no, now we have a problem.

    It is more like:

    Right. How do we solve this?

    And somewhere beyond the problem, I can often already see what comes next: a new solution, a success, an invention or an achievement. Difficult situations do not drain my energy. They generate it.

    A long, secure career or a long, secure stretch of boredom?

    I probably have a higher-than-average tolerance for risk. That does not mean I seek risk for its own sake. I do not need to go skydiving before breakfast. On the other hand, I do not place much value on the sense of security offered by a long, steady career if the other side of the scale holds slowness, boredom, greyness and the feeling that nothing is being developed any more. Security is not a very attractive reward if the price is stagnation.

    This is also reflected in my CV. Over a career spanning roughly 25 years, I have worked for around ten companies. Typically, I have changed roles or companies every 2–4 years.

    On paper, of course, that can lead to one quick conclusion:

    That man does not seem able to stay put.

    Exactly right. I cannot, if staying put means standing still.

    But every significant move in my career has taken me forward: into something new, bigger, higher or more demanding. At the same time, my responsibilities, expertise and playing field have expanded. I have also run businesses alongside salaried employment. Looking back now, a fairly clear pattern begins to emerge.

    I have not built a single career.

    I have built a portfolio of expertise.

    Charles Handy’s shamrock – a company is no longer made up solely of employees

    One of Handy’s best-known models is the Shamrock Organisation, based on the idea that the organisation of the future resembles a three-leaf clover.

    The first leaf consists of the company’s professional core: key leaders, specialists and other people whose expertise and responsibilities form the core of the organisation.

    The second leaf consists of contractual expertise – external professionals, service providers and specialists.

    The third leaf is the flexible workforce, used according to need and circumstance.

    Handy was therefore describing an organisation that no longer needed to retain all its expertise permanently on the company payroll. That sounds quite normal today. But the idea was first presented in the late 1980s.

    And this takes us directly into the world of fractional and interim work. They should not be forcibly equated one-to-one with the second leaf of Handy’s shamrock – today’s operating models have evolved further and their boundaries overlap to some extent.

    The basic idea is still the same.

    A company does not need to employ all the expertise it requires.

    It needs to have access to the right expertise when it is needed. That is a huge difference.

    A portfolio does not mean a random collection of gigs

    Portfolio entrepreneurship can easily be misunderstood. A little consulting here, one project there, a couple of board positions, one training day and something else that someone happens to pay for. That is not a particularly good portfolio. It is a desk that no one has tidied.

    Find a Fractional’s material on portfolio careers for senior executives makes an important distinction here: a strong portfolio is not a collection of random assignments. It should be built around a clear professional value proposition. There should be a recognisable common thread running through the different clients and forms of work.

    This idea resonates with me. From the outside, my portfolio may look very broad:

    • Freight forwarding.
    • Logistics.
    • Business management.
    • Sales.
    • Marketing.
    • Processes.
    • Systems.
    • Business development.
    • Change management.

    But they are not separate, unrelated boxes. The common denominator is solving business problems.

    • Where are we now?
    • Why are we here?
    • Where do we need to get to?
    • What is stopping us?
    • And what is the first thing we do on Monday morning?

    That is my common thread.

    Fractional does not mean half a leader

    The term fractional executive is still relatively unfamiliar in Finland. The word fractional refers to a company using only part of an executive’s capacity. For example, a company might engage a Fractional CFO, CMO, CTO or Development Director for one or two days a week.

    But this is the most important point of the entire model: Capacity is fractional. Responsibility is 100%

    This is precisely where Find a Fractional draws the distinction from conventional consulting. A consultant usually examines the situation and recommends a solution. An adviser challenges, coaches and contributes expertise to decision-making.

    A fractional executive becomes more closely involved in the organisation. They participate in its management. Make decisions. Set priorities. Direct people. And take responsibility for ensuring that something actually happens.

    This suits my way of thinking far better than classic consulting. I find it hard to imagine standing on the sidelines while a client has a problem, writing a 46-page PowerPoint about it and then walking away. I want to see what happens next. Better still, I want to help make it happen.

    What about interim?

    Interim is a close relative of the fractional model, but its purpose is slightly different.

    An interim executive usually joins a company for a fixed period and commits substantially more time – sometimes effectively working full-time. The reason might be a sudden leadership gap, a corporate crisis, a major transformation, an integration, a turnaround or some other phase in which an experienced leader is needed immediately, but there is neither the time nor the desire to make a permanent hire.

    In a fractional arrangement, a company buys a share of an executive’s capacity on a longer-term basis. In an interim arrangement, it often buys almost the whole man or woman for a fixed period.

    In both models, however, the essential element is action. Not merely giving advice. That is precisely why I believe these two models fit well within the same portfolio.

    At one company, I might work intensively in an interim role for a few months. At another, the assignment might be a long-term fractional role one day a week. At a third, I might solve a clearly defined commercial or operational development challenge.

    And at times, I can lecture, train, coach or write.

    The same expertise.

    Different dosage.

    Perhaps my CV was not restless after all

    When I look at my career through this lens, many things fall into place in a new way. I began in the automotive industry as a car mechanic. From there, I moved to my father’s freight forwarding company and began studying business. After that, my world began to expand rapidly:

    Freight forwarding. International logistics. Sales. Management. Business development. Contract negotiations. Training.

    Business trips across Europe, to China, Hong Kong and Turkey.

    I have built two detached houses. Founded companies. Worked both as a salaried executive and as an entrepreneur. My personal life, too, has included several phases, homes and relationships. At no point, then, have I really lived along a single straight line. I have lived through a series of projects, phases and new beginnings. Many good outcomes that support one another. Failures too, but they do not break any straight “line of progress”. They serve as lessons and guide the next stages of my life in the right direction.

    If you have never stumbled, you do not know how to get back up. If you have never failed, you do not know what to avoid. If you have never taken a wrong turn or made a single mistake, you have succeeded in sidestepping, circling around and avoiding the moments that truly matter. But that skill will not build a successful life or a finely tuned business. That mentality only dodges, hesitates and avoids responsibility. It fears the worst and hopes for the best. If you are afraid of slipping, you should not go outside in winter. But then you miss out on a great deal of life.

    By accepting possible setbacks, failures and losses, we build the profile of a true winner. Every setback teaches us something. All of them can be overcome. And real expertise is only put to the test when something goes wrong, a process stalls and genuine doers are needed – not mere “yes-men” standing around with their hands in their pockets.

    Looking back, my entire way of life has been something of a portfolio. 

    I can turn my hand to many things. At times, that has been a difficult trait in an environment where people are expected to fit into a single job-title box. In a portfolio environment, the same trait can become quite valuable.

    Broad expertise does not mean having to do everything

    There is also a danger here. When people are capable of many things, they can easily start to imagine that they should sell them all. They should not. I have a strong background in freight forwarding and logistics. It is the deepest area of my expertise and the environment in which I have spent much of my career. But over the years, I have also accumulated a great deal of expertise that does not really belong to freight forwarding.

    Sales management is not freight forwarding.

    Business strategy is not freight forwarding.

    Building processes is not freight forwarding.

    Leading an organisation is not freight forwarding.

    Identifying the problem in an underperforming company is not freight forwarding.

    These are business skills. That is why I do not want to limit my future clients to the logistics sector. Freight forwarding gives me a strong home field, but I must also be able to apply my expertise beyond it.

    I have always liked out of the box thinking. In fact, the whole expression is slightly amusing. If the solution lies outside the box, why on earth is everyone still sitting inside it?

    The Second Curve – the next curve must begin before the first one ends

    Charles Handy’s The Second Curve offers another perspective on this. Put simply, the idea of the second curve is that organisations – and people – should have the courage to build the next phase before the old way has been completely exhausted. If change is only set in motion once the first curve is plunging downwards, there are usually already fewer options available.

    Throughout Handy’s thinking runs the need to challenge familiar structures and reinvent the future before circumstances force us to do so. I like the idea. For me, portfolio entrepreneurship is precisely this kind of second curve.

    The first curve built my expertise. I was an employee. A supervisor. A salesperson. An executive. A CEO. An entrepreneur on the side.

    Now the question is:

    What happens if all that experience is no longer tied to a single organisation? What if the expertise accumulated over 25 years is used to solve the problems of several companies at the same time? To me, that is a far more interesting question than what title I might hold in my next job.

    A portfolio is not an easier way to work

    At this point, it is worth dispelling one potentially romantic notion. Portfolio entrepreneurship is not synonymous with freedom, a laptop and a cappuccino on a sunny terrace. Portfolio entrepreneurs have to build for themselves the machinery that an employer previously provided ready-made.

    • Sales.
    • Client acquisition.
    • Pricing.
    • Contracts.
    • Administration.
    • Calendar management.
    • Risk management.
    • Personal visibility.

    And above all, securing the next assignment while taking proper care of the current ones.

    Find a Fractional also highlights fluctuating income, the differing demands of clients, continuous business development and the danger of accidentally combining several fractional roles into one impossible 120% working week. A portfolio must therefore be managed like any other business.

    This does not frighten me. Quite the opposite. There is a game in it. And I like games with lots of moving parts.

    One career or an entire portfolio of expertise?

    Perhaps the biggest change ultimately takes place in one’s own mind. In traditional working life, a person asks:

    What am I?

    • A CEO?
    • A Sales Director?
    • A freight forwarder?
    • A consultant?
    • An entrepreneur?

    With portfolio thinking, the question changes.

    What do I know how to do, and what can I achieve?

    To me, that is a much better question. I do not have to choose just one box. In one situation, I can be an interim executive. In another, a fractional Development Director. In a third, someone who builds sales. In a fourth, a coach. In a fifth, a trainer.

    The role changes. The core expertise does not.

    And perhaps that is precisely why the whole idea of portfolio entrepreneurship feels exceptionally natural at this point. I am not building an entirely new career for myself. For the first time, I am consciously assembling the pieces of the career I have already built.

    Portfolio entrepreneurship, then, is not an escape from permanent employment for me.

    It is a way to put 25 years of experience to work more effectively.

    Perhaps, in the end, I did not switch from one career to another. Perhaps I simply stopped trying to fit myself into a single job.

    P.S. In Finland, Pia Kiviranta is a strong advocate for these ideas. Her content and services are also well worth exploring: https://piadotsinterim.fi

    Background and sources

    • Charles Handy: The Age of Paradox
    • Charles Handy: The Second Curve – Thoughts on Reinventing Society
    • Charles Handy’s thinking on the Shamrock Organisation and the portfolio career
    • London Business School: The Shamrock Organisation
    • FindaFractional: How to Build a Portfolio Career as a Senior Executive

  • A micromanager sees trees. A real leader sees the forest.

    A micromanager sees trees. A real leader sees the forest.

    Imagine two leaders.

    Both have become lost in the forest with their groups.

    Evening is closing in. The temperature is dropping. One person has an injured leg, and another is already starting to lose hope.

    They need to get out of the forest before nightfall.

    The first leader looks around.

    He sees a great many problems.

    One person is standing in the wrong place. Another is holding the axe incorrectly. A third has taken three steps without prior approval. A fourth appears to be thinking for themselves.

    The situation is serious.

    The leader acts immediately.

    – Do not touch the trees.

    – Do not climb onto rocks.

    – Do not leave the group.

    – The axe may only be used with separate authorisation.

    – Every step must be reported before it is taken, while it is being taken and, preferably, after it has been taken.

    Especially afterwards.

    Only then can it be assessed whether the step was permitted in the first place.

    When direction is missing, the rulebook grows

    The first leader does not know where they are.

    He does not know which direction they should take.

    He does not know how to bring the injured person along.

    But he knows one thing for certain:

    The current Company Policy is not long enough.

    It needs a new appendix.

    The appendix needs a sub-appendix.

    And the sub-appendix needs a clarification on who is authorised to read the original appendix.

    The forest around them grows darker, but the documentation improves by the minute.

    This is important.

    Because if the group freezes during the night, it can be demonstrated beyond dispute in the morning that this happened in breach of the instructions.

    Everything was under control. Except the business.

    Micromanagement looks like leadership from the outside.

    There are plenty of meetings.

    There are plenty of reports.

    There are even more approvals.

    The calendar is full of coloured boxes, emails ping around the clock, and the leader’s name appears in every thread.

    Impressive.

    Except that nothing moves.

    Or if it does, nobody knows in which direction.

    When results deteriorate, a poor leader does not necessarily stop to ask whether the strategy is flawed.

    He asks why people are not following the rules even more precisely.

    When the first control does not help, a second one is added.

    When that does not help either, a working group is established to assess whether the controls are sufficient.

    When the company makes a loss, the rulebook delivers growth.

    So at least something is developing.

    A prohibition is not a strategy

    A poor leader feels safe when everything is forbidden.

    Nobody can make a mistake if nobody is allowed to do anything.

    Brilliant.

    Sales is not allowed to make an unconventional offer.

    Operational management is not allowed to solve a customer’s problem on its own initiative.

    Local management is not allowed to decide a local matter.

    Nobody may take a risk, exercise judgement or move forward until the matter has travelled sufficiently far away to people who know neither the customer, the situation nor the market.

    If a decision takes three weeks and the customer leaves in two, the process has still succeeded.

    Every rule was followed.

    The customer simply behaved incorrectly.

    The micromanager leads through fear

    In the forest, nobody asks anymore:

    – How do we get out?

    Instead, they ask:

    – Am I allowed to do this?

    – With whose permission?

    – What happens if I make the wrong decision?

    – Who will get angry?

    – Would it be safer to do nothing at all?

    The final option is often the safest.

    The organisation learns quickly.

    Not to learn, experiment or solve problems.

    But to protect itself.

    People no longer consider what would make sense for the company, the customer or the outcome.

    They consider which decision will leave the fewest fingerprints.

    It is an effective way to build a company where everyone protects their own back and nobody takes responsibility for the whole.

    A leader, on the other hand, sees the forest

    The second leader looks at the same situation.

    He sees the risks too.

    He too sees the injured leg, the darkening sky and the wet terrain.

    But he also sees something essential.

    These trees form a forest.

    The group is lost.

    Night is approaching.

    And they need to get out.

    He climbs onto a rock.

    Not because he wants to appear bigger than everyone else.

    Not because he needs an audience.

    And not because his title looks more impressive when he is standing on a rock.

    He climbs higher because he can see further from there.

    That is, incidentally, a surprisingly good test of leadership.

    Some people rise higher in an organisation to see the bigger picture.

    Others rise higher merely to make sure everyone else can see them.

    A good leader asks the right question first

    He does not begin by asking who broke a rule.

    He begins with this:

    – What is the situation?

    Then this:

    – What is the most important objective?

    And finally this:

    – What do we need to do now?

    A surprising number of leadership problems would already be solved if these three questions were asked before the first order was given.

    But that requires thought.

    Handing out rules is easier.

    Everyone shares the same direction, not the same task

    The second leader knows his group.

    The two strongest members build a stretcher from trees and jackets.

    The fastest person goes slightly ahead to inspect the terrain.

    The best navigator keeps the group on course.

    The calmest person walks beside the injured member.

    Someone carries the equipment.

    Someone keeps track of time.

    Someone makes sure nobody is left behind.

    Everyone is doing something different.

    Yet everyone is moving in the same direction.

    This is leadership.

    A poor leader tries to make people identical to one another.

    A good leader turns their differences into a competitive advantage.

    Trust looks dangerous to a control freak

    A good leader does not inspect every knot personally.

    He does not dictate the position of every foot on every step.

    He does not require the scout to request approval for every change of direction.

    He defines the objective, the boundaries and the responsibility.

    Then he lets people do their jobs.

    To a control freak, this looks careless.

    But what if someone makes a mistake?

    Good question.

    Someone probably will.

    But a leader understands that people do not develop without making decisions.

    An organisation does not develop if every decision is sucked up to the top floor.

    And a business does not develop if the only permitted course of action is to wait.

    Mistakes cost money.

    But so does an inability to decide.

    Often far more.

    Losses are not fixed by adding fear

    If a company does not know where it is going, closer supervision of its employees will not provide it with a strategy.

    If customers are being lost, additional approval layers will not bring them back.

    If the local market is not developing, removing local decision-making authority will rarely improve the situation.

    If capable people start leaving, it may not be because they failed to understand the latest policy appendix.

    Sometimes they leave precisely because they did understand it.

    A loss-making company might perhaps ask:

    – What do our customers need?

    – What are we good at?

    – Where are we failing?

    – What do we need to change?

    But control-based leadership asks:

    – Who made the decision without permission?

    That is an excellent question if the objective is to find someone to blame.

    A poor question if the objective is to find a way out of the forest.

    An organisation led through fear stops telling the truth

    This always happens gradually.

    At first, people report problems.

    Then they notice that the person who raised the problem is made to explain the problem themselves.

    Next time, the problem is phrased a little more attractively.

    Then the most difficult parts are removed.

    Eventually, the report states that the situation is under control.

    The company is standing in the middle of the forest, but the PowerPoint shows a green arrow pointing upwards.

    The leader is pleased.

    Green is a good colour.

    The only minor challenge is that nobody dares to mention that the sun set an hour ago.

    Company Policy can protect the company

    Or the leader from the company.

    Good guidance makes work easier.

    It explains where the boundaries lie and helps people make better decisions.

    Poor guidance is often written afterwards to conceal a lack of leadership.

    When direction is unclear, a process is written.

    When responsibility is unclear, an approval matrix is written.

    When trust is absent, a control model is written.

    When results fail to appear, a report is written explaining why somebody else failed to follow the model.

    The paperwork increases.

    Movement decreases.

    A leader does not need to know everything

    But a leader must understand what matters.

    He does not need to be the strongest carrier in the group.

    He does not need to be the fastest runner.

    He does not need to navigate better than the navigator.

    A leader’s job is not to outperform every employee at their own work.

    A leader’s job is to get the best people to apply their expertise in the same direction.

    This sounds simple.

    That is exactly why it is so difficult.

    It requires a leader to accept that somebody else knows more about something.

    And not everyone is capable of that.

    In the end, both groups produce a result

    The first group spends the night in the forest.

    Everyone knows exactly what they are not allowed to do.

    Every decision has been documented.

    Every deviation has been recorded.

    And in the morning, an internal investigation is launched into why the group failed to achieve its objective.

    The second group gets out before dark.

    Not every original plan was followed.

    The route was changed.

    People made their own decisions.

    Someone used the axe without three-stage approval.

    A complete administrative disaster.

    Except that everyone made it to safety.

    A leader sees the forest

    People in companies do not usually literally freeze to death.

    They merely lose customers, money, capable people and years.

    More slowly.

    More neatly.

    In accordance with approved processes.

    The micromanager notices every branch placed incorrectly.

    The leader notices that the entire group is lost.

    And when night is approaching, the company does not need another prohibition.

    It needs direction.