Plan ahead or wing it? Experts reveal which approach serves us best

There are merits and downsides to both strategy and spontaneity

People with a Type A personality prefer to plan and need structure, while Type Bs are more spontaneous and flexible. Getty Images

For those who plan their way through work (or, indeed, life) with a strategy and spreadsheet in hand, the idea of winging it can feel anxiety-inducing. The more spontaneous among us, however, might argue that detailed planning not only lacks on-the-go creativity and problem-solving, but ultimately any sense of thrill.

Each party is convinced their approach is the ideal one, but both strategising and spontaneity can have merit, especially within different industries, job roles, environments and situations.

“Being someone who naturally likes to plan things can be a great advantage in environments where predictability is important, decisions need to be taken promptly and other people who need to plan are involved,” says Roh Hafez, a life coach at The Hundred Wellness Centre. “Being someone who naturally prefers spontaneity and surprises rather than plans and routines is great in environments where there is low predictability and a lot of change and uncertainty.”

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Personality clash

“Planners often create clear steps to reach their goals, use resources wisely, and avoid unnecessary problems along the way,” says Lindi Nhlapo, a counselling psychologist at Thrive.

“Traditionally, this group of people would be recognised as a Type A personality because of their strong focus on structure and achievement. You may know someone who has their life organised around schedules, lists and carefully mapped out goals; for them, structure brings peace of mind.”

As for someone who is more impulsive, Nhlapo explains: “Those who adopt a more easy-going approach relate to what is traditionally called a Type B personality. These individuals tend to take a more flexible and easy-going approach, which allows them to adapt quickly and respond to unexpected changes.”

Experts cite teaching roles as typically requiring more planning compared to stockbrokers. Getty Images

For Type As, uncertainty is the enemy. They work hard to tie up loose ends and dot the i's and cross the t's dotted ahead of schedule.

“Planning makes me feel calm,” says Karla Hirtescu, a customer references lead based in Dubai. “I love my lists, my calendar and having things organised. It also gives me a sense of control, which helps me focus. I don’t have to keep everything in my head, because it’s already written down.”

Pros and cons of preparation vs spontaneity

Work and life choices often dictate the approach a person either naturally takes or is forced take.

“Take for example a teacher,” says Hafez. “By its nature, the job needs clear plans for the day, week and academic year. Without exercising this skill, a classroom and its students will end up in chaos. Then think of stockbrokers or business consultants. Those people thrive on thinking and acting on their feet. This skill of being flexible and adaptable allows them to navigate situations that may be overwhelming for the planner.”

A well-constructed plan can ensure no detail is overlooked and a team of people each know what is expected of them and when. Predictability and prompt decision-making can reduce anxiety and unknowns; however, too rigid an approach to planning can make it difficult to react to change and pivot quickly if necessary. Over-planning can also lead to perfectionism.

“Rigid planners may struggle with flexibility and risk missing out on spontaneous opportunities,” says Nhlapo. “With higher neuroticism, individuals may experience stress, impatience or pressure more intensely, which can push them to achieve but also increase burnout risk.”

A hybrid approach, which entails recognising whether a situation requires strategising or spontaneity, might work best. Getty Images

For those who like to wing it, adaptability is key, allowing for a flexible approach to work or life. Typically unfazed by surprises, such people can adjust quickly to fast-changing situations, but the approach can bring challenges.

Spontaneous souls may find themselves losing out on experiences because they did not plan in advance, such as with events or holidays, and may find it tiring to be constantly reacting to situations as opposed to staying on top of them over time.

Adopting a hybrid approach

While the two personality types may find it difficult to relate to the other, both strategic planning and the ability to react to change are vital skills.

High-profile strategists have long extolled the virtues of adopting a hybrid approach. As statesman and former British Prime Minister Winston Churchill noted: “Plans are of little importance, but planning is essential.” Likewise, in his 2018 letter to shareholders Amazon’s Jeff Bezos wrote: “Most decisions should probably be made with somewhere around 70 per cent of the information you wish you had. If you wait for 90 per cent, in most cases, you’re probably being slow.”

Hafez stresses it is important to realise that our natural preference isn't the only valid way. “Being a planner by nature does not mean you can’t be flexible and spontaneous, and vice versa.” She encourages people to recognise that our default approach doesn't always work out, and try and spot opportunities and situations where stepping outside our comfort zone might be beneficial. “We should ask ourselves what the best approach is to a particular situation or problem.”

One way to do this is to reflect on situations that have left you feeling stressed, as this is a typical indicator that your approach is not serving you. If detailed planning is leaving you feeling tense or exhausted, it may be time for a little spontaneity, and if a lack of structure creates feelings of anxiety or unproductiveness, more structure may be needed.

“As a planner, I don’t like to be tied to a schedule or a certain course of actions, and as a winger, I don't like bad surprises,” says Dubai-based estate agent Clementina Kongslund.

“On holidays, I love to have the departure and arrival dates planned, but during them I don’t mind wandering down side streets, eating something I can’t pronounce and pretending I understand the bus system when in reality I’m just hoping I end up somewhere scenic.”

She adds: “I have no problem switching and have started to take things more lightly and focus on what I can control and improvising what I cannot. Planning is good for knowing the options, winging it is good for surprises.”