Working With Your Sister: 5 Realities Of Running A Business With Your Sibling

Over the last few years, I’ve come to realise that there are two types of people in this world. When describing the job (and I use that term loosely) that Claire and I do, people tend to react in one of two ways. There are those that clutch their hands to their chests and smile; the skin around their eyes crinkling into happy little ravines. ‘You get to travel and work with your sister? That must be wonderful’, they say. Their eyes go a little misty and they radiate sentimentalism like a Clintons birthday card. On the other hand, there are the cynics of this world – the realists. ‘Working with your sister must be awful’, they insist. ‘In fact, I couldn’t think of anything worse’. They often look a little haunted or disturbed, like Claire and I are a nightmarish vision haunting their sleep.

Of course, when it comes to deciding which camp Claire and I fall into – the sibling sentimentalists or the feuding family – the choice is surely obvious. For nearing five years we’ve run a small business together – travelled the world together. We regularly abandon our friends, family, other siblings, husband and partner, for a life on the road – together. Our bank balances, agendas, working life, contacts, colleagues and personal lives revolve around one shared entity: Twins That Travel. Surely, if there is anyone in this world that celebrates siblings working together – it’s us. The travelling twins.

If only it were that simple.

You see, working with your sister is both a dream and a nightmare. A sickeningly happy experience featuring shared sunsets and bucket list moments. But it’s also a rowing, screaming trauma – one accompanied by the jarring soundtrack of slammed doors, tears and threats to abandon one another inside foreign airports. Running a business with your sibling is both the best and the worst decision you’ll ever make – a never-ending cycle of highs and lows. It’ll make you want to squeeze your sister oh so tightly, before that squeeze inevitably turns into a headlock.

Indeed, running a business with my sister has meant that we’ve experienced both the very best – and the very worst – of each other.

But, don’t let this put you off. If you are considering working with your sister, or setting up a business with your sibling, read on. Yes, the journey will inevitably be difficult. You might even get into a physical fight inside a hotel room in Vienna – pulling each other’s hair and wrestling one other to the floor. Maybe you’ll have a showdown in a Florida gas station; one sister flinging a bottle of water over the other.

But, I promise that it’ll also be a journey that you won’t forget; one that’ll ensure your relationship is richer, more resilient and ultimately – happier – for it.

A Problem Shared (Is A Problem Halved)

Deciding to leave behind the shackles of the 9-5 is incredibly daunting. I’ve previously written about how difficult I found the whole transition; the month of January 2018 spent suffering from some form of rat race induced Stockholm Syndrome. I pined for a routine that I’d previously despised. I missed my Outlook diary and my meeting reminders. I missed passive aggressive emails signed ‘Regards’, and the smell of the staff canteen. I missed having my boss’ inane admin tasks dumped on me, all in the name of ‘experience’.

Of course, compounding all this was the inevitable stress that comes with self-employment and the realisation that from hereon in, my financial security was inextricably linked to my own, personal success. There was to be no hiding amongst the nuts and bolts of an organisation, no corporate shadow to cower in. Instead, self-employment shone an unflinching spotlight on my own determination and strengths; revealing an entirely strip-backed version of myself.

Whether my business sank or swim was all down to me. Or was it?

I can’t imagine how hard the pressure of self-employment must be to manage alone. In fact, even if I had colleagues – friends or peers that were also invested in my new business – I would still find it a struggle. I shudder at the thought of having to stoically hold back my desire to cry hysterically at the idea of my house being re-possessed. I can’t imagine not ringing my business partner late at night, asking whether they think I’ll end up on a Channel 5 Show called: ‘Young, Failed and Skint’.

It’s here that working with your sister – or starting a business with your sibling – offers so much (emotional) relief. Realising that not only are you saved from shouldering the burden of self-employment alone, but that you needn’t maintain (so much) professional decorum, can be enormously empowering.

Whether it be worries about income, anxieties over a tetchy email, or concerns that your latest Instagram photo has bombed, each problem is shared with your sister and as a result, miraculously halved. There is something incredibly reassuring about this, particularly when you can be entirely honest about your concerns.

We also find that when a problem rears its ugly head, it tends to be only one of us that worries. Whilst one twin chews neurotically on their fingernail (‘someone left a slightly negative comment on the blog, we’re over’), the other jumps to the rescue – offering rational, objective reassurance (‘it’s not that negative and it’s just one comment. We will live to see another day’).

It’s this dynamic – the story of The Worrier and The Rationalist – that has saved us time and time again. It’s stopped us from drowning in irrational worries and helped us to bounce back happier, more confident and fully reassured.

Blood Is Thicker Than Water

When setting up a new business, it’s tempting to pull in the help of others. Why not expand your travel blogging business to include your best friend? Another blogger? Your neighbour’s cousin?

Of course, many people do this and are enormously successful as a result. However, in the fickle world of self-employment and considering the significant pressures that come with it, perhaps there is no one better to work with than your sibling.

I’ve lost count of the number of times that the stress of running Twins That Travel has resulted in Claire and I sending screechy WhatsApp voice notes to each other, or man-handling one another whilst taking a Skype call with a possible client (silently, of course). We’ve had disagreements, arguments and identity crises; each one fuelled by the demands of running our blog.

Thank goodness we are sisters.

Indeed, if I were to be running Twins That Travel with a friend or fellow blogger, I’ve no doubt that we would have gone our separate ways by now. Brought down by the stress and tension of self-employment, and as two individuals with no loyalties to each other past the fact we quite like one another, it’s all too easy to imagine such a partnership falling apart.

However, when working with your sister – or running a business with your sibling – your relationship comes complete with an industrially strong dose of resilience. A hefty insurance policy of its very own. After years together and a lifetime of rows behind you, sibling relationships are made from Teflon: nothing can stick to them, not even the worst of arguments. Having grown up together and bound by blood – I’d even go as far as to say that siblings make for the strongest of business partners.

From experience, I know that however bad the disagreement, after an hour or so, the dust will settle and it’ll be business as usual. You see, no insult is too cutting when ultimately – you’d take a bullet for one another.

Colleagues or Sisters?

Now that the sickly sweet advantages of working with your sister are out of the way, let’s get to the nitty gritty: the challenges of running a business with your sibling.

Whilst working with your sibling can provide your business with a strong foundation, there are other aspects of the sisterly relationship that can cause these sturdy roots to splinter.

As sisters, there is an unspoken rule that we can contact each other wherever we like, whenever we like. All the livelong day, if we so wish. In fact, Claire and I Whatsapp message nearly all day, every day; a constant stream of consciousness passing back and forth between our phones.

This is all well and good when those messages only regard life’s every day details: a dress we like, what we are having for dinner, whether or not we’ve irritated another family member. Yet, when these messages begin to concern work, business or demands, the mood can begin to change.

Imagine it’s a Saturday afternoon and you’re out enjoying lunch with your significant other. You’re gazing lovingly into each other’s eyes and are about to open a bottle of wine. However, your phone rings. It’s your sister – she wants to talk. You ignore it, turning your phone over. But then it bleeps again and this time it’s a message. ‘Can I ask a quick question about the blog post?’ it says. You try to ignore it, but the guilt begins to build.

Five minutes later and the phone rings again – it’s your sister. ‘I know you’re out to lunch but can we chat for ten minutes? I’m sat in front of my laptop trying to get this done for both of us’. You sense her irritation and relent, your partner boring holes into the back of your head as you take the call.

In a traditional, professional setting, this sort of thing is unlikely to happen. If it did, you would either turn off your phone or make a complaint to HR about unfair harassment. Yet, when it’s your sister, no such professional boundaries exist and the HR Department is – at best – represented by your own mother.

Instead, working with your sister is like a professional and personal free for all – a vortex in which neither of you can entirely relax, just in case the other one wants to work.

It’s these lack of boundaries and clarity that prove our greatest stressor. It regularly seems that if one sister wants to vegetate on the sofa, the other one is dangerously caffeinated and focused: ready to take over the blogging world. Whilst one is therefore made to feel guilty, the other feels resentful – a dynamic that will shift back and forth as the afternoon unfolds.

If I had one piece of advice for siblings considering working together, it would be to clearly define the boundaries surrounding your working relationship. How will you work together? Will you have days off when you can’t contact one another? What happens if one sibling wants to work, but the other wants to watch the Gilmore Girls?

Deciding on these ground rules could be the saving grace of your working relationship: affording you both valuable downtime to be ‘just sisters’, rather than colleagues.

The Fork in the Road

So, you decided to start a business with your sibling and all is going well. Your venture is flourishing and you’ve achieved many of your objectives. You might wonder what all the fuss was about: working with your sister was the best decision you ever made.

Until, that is, one of you gets a case of itchy feet.

In a normal business setting, itchy feet is normal – accommodated for, in fact. When the itching begins the person will be encouraged to look towards a promotion or, if they wish, opportunities elsewhere. The owner of the itchy feet leaves their role and a replacement steps right in, with no negative impact to the wider organisation. This cycle continues and perpetuates, propelling the business forward as talent joins and talent leaves.

Yet, when you run a small business with your sibling, itchy feet isn’t just a harmless affliction; it is cancerous, eating away at the body of your business.

Claire and I are more than aware that Twins That Travel is (perhaps terrifyingly) dependent on us both. It’s not called ‘One Twin That Travelled’ or ‘Tales Of A Deserted Twin’. We understand that any interest in us is largely down to the fact that we are identical twins, and the dynamics and mishaps that come with that. Claire without me, and me without Claire, would not be enough; we simply wouldn’t have a business.

This is (of course) always at the back of our minds, and we both perhaps dread the day that the rug is pulled from under our feet, as the other decides to explore pastures new. As we get older – societal pressures to ‘settle down’ piled on our heads – it’s a feeling that’s only got worse.

Before deciding whether you want to work with your sibling, I’d therefore advise that you have ‘the chat’: the ‘where is this going?’ talk. What will you do if one of you wants to leave the business a few years down the line? Or if one wants six months off to find themselves in India? What will you do if your sister launches her own business one day? How will you feel?

Before you set up a business with your sibling, make sure you are prepared for any future forks in the road; nobody likes to be derailed.

Bravery In Business

Before we wrap up this blog post, I want to finish on a high – delivering my conclusion as to what it is like working with your sister.

Plot spoiler: it makes for a happy ending.

Working for yourself is a high stakes business. Whilst you’re undoubtedly driven by a determination (read: fear) to succeed, you’ll also find yourself walking something of a tightrope regarding how far you’ll go to make this success a reality. Indeed, how ambitious will you be? How big a risk are you willing to take? How far out of your comfort zone will you inch?

I have no doubt that had I been running Twins That Travel alone (albeit, with a different name), I’d not have taken a fraction of the risks, chances and opportunities as I have done with Claire by my side.

Running a business with your sister provides you with a sense of infallibility – of invincibility. Of course, there is always the prospect that you might fail, or that your venture will go down in bright, burning flames. But, if it does, at least it does so for your sister too. You’ll simply pick up the pieces together.

Throughout our four years of blogging, we have been offered some fantastic opportunities that I would have certainly been too anxious to agree to alone. From photoshoots to television opportunities, business ideas to public speaking, I have agreed to each and every one of these as I know that Claire will be there too: my equally nervous, yet committed, wingman.

It’s a little surreal just how much confidence our relationship brings: a combined bravery that allows us to take on things that would be too overwhelming if alone. I often wonder if a friend or colleague would provide me with the same feeling of reassurance or support, but I think the answer would probably be ‘no’.

Of course, there might be times when this unbridled bravery results in disappointment. Maybe, caught up in each other’s excitement, we haven’t thought an opportunity through, or have assumed that the other has carefully audited or assessed the situation. Yet, these instances are far outnumbered by the glittering sense of achievement we’ve both felt when finding ourselves miles away from our comfort zone.

Working With Your Sister: Final Thoughts

In summary, it’s perhaps this combined superpower that makes working with your sister just so rewarding. On my own, I am only half as brave and half as daring. On my own I can make rash decisions, or can alternatively retreat into shyness and insecurity. On my own, I am only one half of Twins That Travel. Yes, being alone might also mean half the fights and half the stress, but it would also mean missing out on a chapter of my life that has – without a doubt – been the most memorable yet.

So, if considering working with your sister – or running a business with your sibling – my advice to you would be: go for it.

Other blogs you might find interesting:

• The Realities of Being an Identical Twin
• The Realities of Self-Employment (Podcast)
• What Is It Like To Be A Twin? (Podcast)

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