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Knowing When to Wait and When to Walk Away

December 13, 20254 min read

A few years ago, I was given an orchid. It flowered beautifully for a short time and then, for what felt like years, it did absolutely nothing interesting at all. No flowers, just a green stalk with a few spiky offshoots and a set of healthy-looking leaves.

With most plants, I would have binned it long before. A brown twig in a pot is not particularly uplifting. But this one stayed green. The leaves were strong, the roots looked alive, and something about it suggested there was still potential there, even if there was no visible reward.

A few weeks ago, new growth appeared. Buds followed. I am now waiting for the flowers to open again, two years later.

That orchid came back to me recently when I was thinking about one of my businesses.

Most of my businesses have returned to pre-pandemic performance. One did not. It requires a sizeable team and significant resources to run, and for a long time, the numbers simply did not justify the effort. The question of whether to close it or invest in it sat heavily with me for months.

This is one of the hardest decisions any business owner makes. When do you keep going, believing that something is still there beneath the surface, and when do you accept that it is time to stop?

I am a big believer in instinct, but instinct on its own is not enough. It has to be supported by data. With the orchid, the data was the condition of the leaves and roots. It told me the plant was alive, even if it was dormant. It was not dead, it was just not thriving yet.

In business, the equivalent data is harder to read, but it is there if you are willing to look honestly.

I often see business owners doubling down on something simply because they have already invested time, money and energy into it. This is understandable, but flawed thinking. That investment is already gone. Whether you continue for another year or close it tomorrow, you will not get it back. The decision has to be based on future viability, not past effort.

When I am weighing up whether to persevere or walk away, I look at several things. Has the market fundamentally changed? Are similar businesses struggling, or is it just mine? What do enquiry levels actually look like, not what I hope they are? Have margins shifted, and if so, why? Are sales conversions holding steady, improving or declining? How much growth has there been in the last twelve months relative to the effort required? And crucially, do I still want to do this work?

I also force myself to answer harder questions. What are the real consequences of investing more time, money and focus into this? Can the product or service be adapted to make it more cost-effective or more relevant? Or am I trying to revive something that no longer fits the world it is operating in?

In this case, after looking at the data, drawing on experience and listening to my instinct, I decided to give the business another twelve months. Not vaguely. Properly. With dedicated resources, clear funding and defined targets. I also set an absolute decision date. If it did not hit agreed benchmarks by that point, I would stop.

What mattered just as much is what happened alongside that decision.

While I was investing in growth and direction, I was also preparing the business to be sellable. Systems were tightened, processes documented, finances cleaned up. I had tentative conversations with people who might be interested in buying it. My eggs were firmly in two baskets. I was open to success, but prepared for exit.

That business was TtMadrid and here is the update!

Those twelve months were worth the wait. TtMadrid will never return to its pre-pandemic model, and that is fine. What it has become is a leaner, more focused business that is growing steadily at around 30 percent year on year. AI and technology have allowed us to keep costs under control and operate far more efficiently, and we have made a deliberate effort to stay ahead of the curve technologically rather than chasing scale for its own sake.

The decision to wait was not about blind hope. It was about informed patience, paired with a clear fallback plan.

Keeping a business alive when it has no business being a business helps no one. But breathing life back into something that still has solid foundations, if you are willing to resource it properly and make hard decisions along the way, can pay off financially and strategically.

The key is knowing the difference.

I started as a solo entrepreneur with more ideas than time, learning through trial and error how to turn what I loved into something sustainable. Over time, that one small venture grew into several profitable businesses, including an educational agency, a language centre and a university partnership, all built on what I call the boring business basics.

Natasha Kennedy

I started as a solo entrepreneur with more ideas than time, learning through trial and error how to turn what I loved into something sustainable. Over time, that one small venture grew into several profitable businesses, including an educational agency, a language centre and a university partnership, all built on what I call the boring business basics.

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