The Realities and Rewards of Running a Sibling Business


Today is National Sister Day and this is an opportunity to celebrate and cherish the bond between sisters. Ever since we were teenagers my sister Megan and I fantasized about starting a business together. But our adult life took us on divergent career paths that didn’t seem to have any common ground. She is an accountant and lawyer and although I have significant experience in developing financial education programs from my years at the American Institute of Certified Public Accountants (AICPA), my specialty is PR and marketing. After years in the corporate circuit, my sister and I have both started our own individual businesses and often tap into each other’s ‘world’ for advice or guidance.

Megan and I are 13 months apart and growing up, it was clear that we had different personalities and interests. We grew up in a home where there was a lot of support but also a lot of fun and laughter. Our mantra was: if you trip and fall, I will be there to help you up – but after we have a good laugh. We always complement each other, but never compete with each other. I can safely say, there has never been any sibling rivalry between us and as we age gracefully together, the mutual respect for each other’s differences has continued to grow.


When COVID hit, like all small business owners, we began to brainstorm about how we could shift our businesses. Somehow it evolved to a discussion about possible projects that we could collaborate on. My sister and I came together to approach our first Request for Proposal (RFP), which required a mix of finance and marketing skills. Although we did not win the bid, we both recognized that there were some synergies just waiting to be explored and we became extremely excited about the possibilities.


For the past year my sister and I have been working together to build SamuelFields Consulting Group (SFCG).  We first had to transform the brand from a legal and financial consultancy into an eLearning enterprise with a network of experts to provide a range of professional services and training in: financial planning, accounting, auditing, financial wellness, management and marketing. Many of these are professional services that we have mastered in our individual careers. After doing a few successful free webinars and getting a favorable response, we knew that SFCG was on the right track in providing financial training and education.  We now do a weekly digital show, Likkle Byte Ideas, send out a weekly newsletter, run training programs for clients, hosted 2 financial wellness conferences and we have some other creative projects in the pipeline. It has been a phenomenal year! Surely, if anyone celebrates siblings working hard together and having fun while doing it – it’s us.


Working with your sister can be a dream. A happy experience of shared ideas, celebrating our strengths and weaknesses and constant laughter. This means that we have experienced both the very best of each other’s strengths, as well as exploring new capabilities and areas of business together. For any siblings who may be considering working together, I promise that it will be a journey that you won’t forget; one that will ensure that your relationship is richer, more resilient and ultimately rewarding.


Halving the Problems. Doubling the Solutions

My sister and I both agree that running a business alone is tough. Entrepreneurship is not a single player sport. There is no corporate shadow to cower in. No company policies to hold us back. Instead, self-employment reinforces our determination and strengths. Whether this business sinks or swims is a responsibility we must carry together. Working with your sister offers so much (emotional) relief. Realizing that not only are you saved from shouldering the burden of self-employment alone, but that you need not maintain (so much) professional decorum, can be enormously empowering.


Whether it be worries about income, anxieties over a cryptic email response from a client, or concerns that your latest proposal has bombed, each problem is shared with your sister and as a result, the burden is miraculously halved. There is something incredibly reassuring when we  identify a particular niche and we bring our unique talents to address it.  It is particularly fulfilling when we can be entirely honest about our insecurities or concerns and then leverage our talents to provide solutions.


We also find that when a problem rears its ugly head, it tends to be only one of us that worries. Whereas one sister jumps into action to shoulder the stress, the other jumps to the rescue – offering rational, objective reassurance. “We will get that sponsorship. I have faith.” Or “Let’s do the research, I know that someone, somewhere has done something similar.”  It’s this dynamic – the story of The Worrier and The Rationalist – that motivates us. It stop us from drowning in irrational worries and helps us to bounce back happier, more confident and fully reassured.


Blood is Thicker Than Water

When setting up a new business, it is advisable to pull in the help of others. However, in the uncertain world of self-employment and the pressures that come with it, there is no one better to work with than your sibling. Indeed, if I were working with another partner or alone, I have little 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, except the fact we quite like one another, it is 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, trust and a shared history.


A sisterly business comes with an insurance policy of its very own. After years together and a lifetime of disagreements behind you, sibling relationships are made from Teflon: nothing can stick to them, not even the worst of disagreements. 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, the dust will settle. And based on our mutual respect for each other both personally and professionally, it will be business as usual.


Business Colleagues or Playmates?

Now that the 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. While 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.


There is an unspoken rule that we can contact each other wherever we like, whenever we like. In fact, Megan and I share Whatsapp messages almost every day; a constant stream of consciousness and creativity passing back and forth between our phones. 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.


However, it is these lack of boundaries and clarity that prove our greatest stressor. I am extremely deadline-oriented and I run a tight operation when it comes to dates and pacing ourselves to be able to address unforeseen circumstances. So there are times when I feel like I am cracking the whip and perhaps making my sister feel guilty. This is a dynamic that if not managed could potentially jeopardize the sibling relationship.


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 brainstorm a new idea? 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 ‘colleague workaholics.’


Bolder In Business

Working for yourself is a high stress, high stakes business. Although 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 big a risk are you willing to take? How far out of your comfort zone will you reach?


I have no doubt that had I been running SFCG alone (albeit, with a different name), I would not have taken a fraction of the risks, chances and opportunities as I have done with my sister by my side. It pushes you out of you comfort zone because you have someone to hold your hand.

It provides a sense of infallibility – of invincibility. Of course, there is always the prospect that you might fail, or that a 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 the past year, we have been offered some fantastic opportunities that I would have certainly been too nervous to tackle alone. From television opportunities, business ideas to public speaking. I have agreed to each and every one of these opportunities because I know that my sister and mentor will prepare me,” said my sister Megan.


It is 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 pursued alone. I doubt that a friend or colleague would provide the same feeling of reassurance or support. Of course, there might be times when this unbridled bravery results in disappointment. Maybe, caught up in each other’s excitement, we haven’t fully thought through an opportunity, or have assumed that the other has carefully audited or assessed the situation. Yet, these instances are far outnumbered by the rewarding sense of achievement that we have both felt when finding ourselves miles away from our comfort zone.


In summary, it is perhaps this combined superpower that makes working with your sister so rewarding. On my own, I am only half as confident, making rash decisions, or alternatively retreating into uncertainty or insecurity. On my own, I am only one half of SFCG. Yes, being alone might also mean half the stress, but it would also mean missing out on a chapter of my life that has – without a doubt – been quite rewarding.


So, if you are considering working with your sister – or running a business with your sibling – my advice to you would be: go for it. I can’t say that this advice holds for all sibling relationships, but it certainly worked for us. Siblings are the best mentors, they know who we are and they inspire us to be our best selves with fairness, kindness and collaboration – even if the love is tough. Having a sister is like having a best friend you can’t get rid of. You know whatever you do, they will always be there for you.



About the Author

Derede Whitlock is a seasoned marketer and former Director of Tourism for Antigua and Barbuda in the USA. She is the CMO of SamuelFields Consulting Group (SFCG). Her sister, Megan Samuel-Fields is the CEO and also a CPA, attorney-at-law and financial coach. As a Community eLearning Partner, SFCG’s dedicated network of experts provides a wide range of professional services and training in financial planning, accounting, auditing, financial wellness, management and marketing.


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  1. May your efforts continue to bear fruit! This is a wonderful expression of progressive sisterhood and enterprise. Thank you and God bless your work.

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