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The Hardest Thing Is Leaving Something That Works

Starting from nothing requires courage. But there is another kind of courage we discuss less often: Leaving something that works.

Failure can make a decision for us. When the money is gone, the customers are not coming or the opportunity has clearly closed, moving on may still be painful, but the evidence is visible.

Success is more complicated. It gives us reasons to remain. It gives us recognition, income, identity, familiarity and proof that we know what we are doing. Other people can see why we built it. They may not understand why we would loosen our grip on it.

Sara Blakely founded Spanx in 2000 with $5,000 in savings.

She retained complete ownership for more than two decades, building it into a global business without outside investment. In 2021, Blackstone acquired a majority stake at a valuation of $1.2 billion.

Blakely retained a significant stake and became executive chairwoman. She did not abandon Spanx, she gave up majority control of the company she had created and personally carried for 21 years.

From the outside, a transaction like that looks like an unqualified victory. Blakely has described the transition differently. She has spoken about mourning the loss of control and the emotional difficulty of separating herself from a company that had occupied so much of her life and mental space.

This is the part of success that receives less attention.

We celebrate the sale but we rarely discuss what it means for a founder to wake up and realize that the organization she created no longer belongs to her in quite the same way.

We ask, “What are you doing next?”

We do not always allow enough time for the founder to understand who she is without the role that previously answered that question.

Blakely also began again with Sneex, a footwear company attempting to combine the appearance of a high heel with the comfort of a sneaker.

She was no longer an unknown founder cutting the feet off a pair of tights in her apartment. She had money, relationships, experience and a recognizable name. But beginning again still required becoming a beginner.

She spent years trying to solve the product problem. Factories declined the work. Some stopped working with her. At one point, she considered abandoning the project because the result was better, but not sufficiently better to justify launching another company around it.

Experience did not remove uncertainty. Previous success did not guarantee that the new idea would work.

That may be one of the quieter challenges of a second act.

The first time, you have little reputation to protect. The next time, the world expects you to repeat yourself successfully.

But growth does not always ask us to repeat what worked. Sometimes it asks us to release it.

This does not mean every successful founder should sell a company or begin another one.

It does not mean discomfort is always evidence that it is time to leave.

There are seasons in which the courageous act is to remain, repair and continue building. But there are also seasons in which something can still be working while no longer requiring the same version of you.

That is harder to explain.

Nothing has collapsed. The opportunity has not disappeared. You may even be good at the work. But a persistent question begins to emerge:

What else could my life contain if this no longer occupied most of it?

Leaving something that works is not necessarily a rejection of what you built. It can be an acknowledgement that it has completed one of its assignments in your life. You can remain connected to what you created without remaining responsible for every part of it. You can be grateful for the identity it gave you while becoming curious about who you might be without it.

Starting Spanx required Blakely to believe in an idea before there was evidence that it would work. Releasing majority control required a different belief: that the success she had built did not have to remain the only proof of who she was.

Perhaps that is why leaving something successful can require more courage than leaving something that has failed. Failure asks you to accept that something is over. Success asks you to decide whether it should still define you.

Not all new chapters begin because the old one collapsed. Some begin when you accept that what you built can continue without occupying all of you, and that you are allowed to discover what else you can build.

The courage to start says, “I believe I can make this work.”

The courage to release it says, “I believe I can build again.”

Until the next note,

– STB

Notes with STB | A content series exploring mindset, money and business.


The Brief Network: Inspiring Stories and Empowering Lessons.

The Making of Funke Akindele: The Talent, Grit and Vision Behind Her Success

Funke Akindele is widely known as Jenifa, the character she brought to life in 2008 and has been identified with ever since. She is an actress, writer, director and producer, and one of the defining names in Nollywood. Her career, however, did not begin with headlines. In the late 1990s she was a young actress going from audition to audition, often landing small parts that gave her little room to show what she could do. Those years brought more rejection than recognition, and the road from there to the box office records she now holds was neither short nor simple.

She began acting in 1996 with waka-pass roles, the brief appearances that rarely carry a name in the credits. In 1997 she was still attending auditions and looking for more substantial opportunities. Her breakthrough came with the television series I Need to Know, where she played Bisi, a secondary school student. The role put her in front of a wider audience, but securing it required some adjustments.

During the pilot, the director felt she was overacting and needed to make her portrayal of a teenager more convincing. She returned to the script and worked on adjusting her performance. Her younger sister also helped by reading some of the lines and acting them out, giving Funke a better sense of how the character should speak and behave. She took the feedback on board, and the role became an important turning point in her career.

By 1999 the series had brought her first million naira, but the larger gain was visibility. She had moved from chasing roles to becoming a face people recognised on their screens.

In 2008 she introduced audiences to Jenifa, a character built on humour, ambition and struggles that many viewers recognised in their own lives. Funke did more than play the lead. She created someone people could quote, argue about and feel close to. The film was followed by The Return of Jenifa and the television series Jenifa’s Diary, which kept the character in front of audiences for years.

Her ambitions did not stop at performance. Through Scene One Productions she moved into producing, writing and directing, taking responsibility for the stories she wanted to tell. Producing means managing people, budgets and schedules, and knowing how to reach the audience a film is made for. She has described herself as more creatively inclined while acknowledging that the business side of filmmaking cannot be ignored. She has also spoken about working with a business manager and team, and the value of partnerships, training and stepping out of her comfort zone.

Her growth as a filmmaker has been reflected in the commercial success of her productions. Omo Ghetto: The Saga grossed over ₦636 million in 2020, outperforming major Hollywood releases at the time. Battle on Buka Street followed in 2022 with over ₦732 million in earnings. In 2023, A Tribe Called Judah crossed ₦1.1 billion, becoming the first Nollywood film to reach that milestone. Everybody Loves Jenifa raised the bar further, grossing over ₦1.88 billion at the Nigerian box office. Her film Behind the Scenes subsequently crossed ₦2 billion, becoming the first Nollywood film to achieve that figure and setting another record across Nigeria, Africa, the United Kingdom and Ireland. These achievements reflect the audience she has built over the years and the growing reach of the stories she brings to the screen.

That growth required discipline. In January 2026 she said she had spent three years building the Jenifa brand and developing other projects, cutting back on social outings to focus on filming, creating content and growing her audience. She stayed close to the details of production, from preparing projects to making sure each scene was properly executed on set. The celebrations that follow a film’s release rest on that unseen work.

Having struggled to get meaningful roles herself, she has turned her attention to the performers coming up behind her. She has said she understands how hard it is to get an opening because she did not receive one easily. Through her productions, she has given other actors a chance and a platform.

Her determination has run through every stage of her career. Describing Jenifa, she said, “She’s a go-getter, she doesn’t want to take no for an answer, and I think I have that.” The comment says something about the connection between the character and the woman who created her. That determination shows in her choices: continuing after early rejections, accepting correction, turning a character into a lasting brand and taking on responsibilities beyond the screen.

There are lessons here for anyone starting out. Her experience with I Need to Know shows that accepting feedback can matter as much as natural talent. Her move from acting into producing shows the value of recognising when it is time to grow beyond what you already know. The recognition came with success, but the preparation and discipline behind it are what sustained her growth.

Funke Akindele’s first opportunity did not set the limit on her ambition. She started with small roles, kept learning, and built films that now draw crowds across Nigeria and beyond.

The Brief Network: Inspiring Stories and Empowering Lessons.

Tope Awotona Built a Billion-Dollar Business from an Everyday Problem. Here Is What We Can Learn

Some of the most successful businesses begin with problems people encounter every day. The difference often lies in recognising that an inconvenience could become an opportunity worth pursuing.

For Tope Awotona, that opportunity came from something as ordinary as scheduling meetings.

Born in Lagos, Nigeria, Tope moved to the United States with his family at the age of 15. After studying Management Information Systems at the University of Georgia, he built a career in software sales, working with companies including IBM and EMC. He also had an interest in entrepreneurship and had made several attempts to start businesses of his own.

However, those early ventures did not succeed. He tried a dating website, an online store selling projectors and another business selling garden equipment. Each attempt came with its own challenges, but they also gave him valuable experience.

His breakthrough came while working in software sales. Arranging meetings with clients often involved lengthy email exchanges, with people going back and forth trying to find a suitable time. He found the process frustrating and began exploring ways to make it easier.

Rather than accepting the inconvenience as part of doing business, he saw an opportunity to solve it.

In 2013, he founded Calendly, a scheduling platform that allows people to share their availability and book meetings without the usual exchange of emails.

Building the company, however, required a significant personal commitment. To fund its development, Tope invested approximately $200,000 of his own money, including his savings and retirement funds, and took on additional debt. It was a considerable risk, especially for someone whose previous business attempts had failed.

His decision eventually paid off. Calendly grew into a global software company, attracting millions of users and major business customers. In 2021, the company reached a valuation of $3 billion, establishing Tope as one of the most successful Nigerian-born entrepreneurs in the technology industry.

His story offers valuable lessons about recognising opportunities, learning from failure, taking calculated risks and building businesses that create value.


1. Opportunity Often Hides in Everyday Problems.

    Awotona saw business potential in something many people considered a routine inconvenience: scheduling meetings. He recognised that a simple problem affecting millions of professionals could become a valuable business opportunity. His experience reminds us to look more closely at everyday challenges because some of the biggest opportunities are hidden in plain sight.

    2. An Idea Is Only the Beginning.

      Building Calendly required more than identifying a good idea. It involved committing personal resources, finding technical expertise, developing the product and working towards a sustainable business. His experience highlights the role of execution, sound decisions and the ability to turn an idea into something people are willing to pay for.

      3. Failure Can Be a Stepping Stone to Better Opportunities.

        Before Calendly, Awotona had tried several business ideas that did not gain traction. Each attempt exposed him to the realities of building a business and helped shape his approach to entrepreneurship. His experience shows that an unsuccessful idea does not have to mark the end of entrepreneurial ambitions.

        4. Conviction Requires a Willingness to Take Risks.

          Awotona committed approximately $200,000 of his personal savings and retirement funds to building Calendly. His decision demonstrates the importance of believing in an idea, recognising its potential and being willing to commit resources towards making it a reality.

          Wealth creation often begins with the ability to recognise value where others see an ordinary problem.

          The Brief Network: Inspiring Stories and Empowering Lessons.

          One Store. Two Days. Fifty Women: How Brief Essentials Is Bringing Breast Health Closer to Women

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          In 2022, an estimated 2.3 million women worldwide were diagnosed with breast cancer, while approximately 670,000 died from the disease.

          In Nigeria, the latest estimates are equally sobering. The International Agency for Research on Cancer estimates that the country recorded more than 44,000 new breast cancer cases and over 21,000 related deaths in 2024. Breast cancer represented almost half of all new cancer cases among Nigerian women.

          These figures describe a public-health problem, but they also represent mothers, daughters, sisters, friends, employees and business owners whose lives—and families—can be changed by a diagnosis.

          Early detection does not guarantee a particular outcome, but the stage at which breast cancer is found can make a profound difference. U.S. survival data show a five-year relative survival rate of more than 99 percent when invasive breast cancer is detected while still localized. That figure falls to 32 percent after the disease has spread to distant parts of the body. Outcomes differ across countries and depend heavily on access to timely diagnosis and quality treatment, but the evidence is clear: finding concerning changes early matters.

          For Brief Essentials, breast health is closely connected to the women the company serves. The Nigerian lingerie and foundation-wear brand has spent 15 years helping women understand their bodies, find properly fitting bras and feel more comfortable discussing concerns that are often treated as private or embarrassing.

          That relationship creates an opportunity to do more than sell products.

          On Friday and Saturday, October 30 and 31, Brief Essentials will turn its store into a community breast-health space for the BE Breast Health Weekend. In partnership with Sebeccly Cancer Care, the company is sponsoring free Clinical Breast Examinations and community breast cancer awareness for 50 women.

          Brief Essentials’ commitment to breast health extends beyond its store. From awareness campaigns and walkathons to educational initiatives and screening events, the company has consistently supported breast health since its early years. At its store, Brief Essentials has hosted two previous screening events, providing women with access to examinations while donating a percentage of sales from the event to support Sebeccly Cancer Care.

          This year’s programme continues that commitment. The Clinical Breast Examinations will be conducted by the Sebeccly team between 10 a.m. and 4 p.m. on both days. Registration is required, and examinations will be provided on a first-come, first-served basis to registered attendees.

          No purchase is necessary to receive an examination.

          However, customers who choose to shop in-store during the two-day event will also contribute to the cause: Brief Essentials will donate 10 percent of sales made during the event to Sebeccly Cancer Care. Customers who require further attention after the programme will also have access to discounted follow-up services from Sebeccly.

          There is a wider lesson in this approach.

          Social impact does not always have to begin with a separate foundation, a large external programme or an enormous budget. Sometimes it begins when a business looks carefully at what it already has: a physical space, a trusted relationship with customers, a platform and the ability to convene people around an important need.

          For Brief Essentials, a lingerie store can also become a place where women learn more about their breast health, ask questions without embarrassment and take an important step towards seeking care when something does not feel right.

          One store cannot solve Nigeria’s breast cancer burden. But for two days, it can bring credible information and professional examination closer to 50 women. It can encourage conversations that continue within homes, workplaces and friendship circles. And it can remind other businesses that community impact often starts with using what is already in their hands.

          The BE Breast Health Weekend will hold on Friday and Saturday, October 30 and 31, from 10 a.m. to 4 p.m. at Brief Essentials.

          Participation is free, but registration is required. Interested women can register through the link provided on Brief Essentials’ platforms.

          A Brief Essentials LoveThatLifts Initiative.

          Connect with Brief Essentials

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          The statistics used are from IARC’s global and Nigeria estimates and the American Cancer Society’s stage-specific survival data. 

          You Built It. Now Give It Wings

          I have often thought about how much building a business resembles raising a child. You nurture it, invest in it, protect it and give it everything you can. In the early days, almost everything depends on you. You make the decisions, solve the problems, attend to customers and sometimes do the work of five people.

          And understandably so. You’re building something from almost nothing. But just as you wouldn’t want your child to depend on you for everything forever, there comes a time when the business you’ve spent years nurturing needs to learn to stand without you.

          And I think this is one of the more difficult transitions for founders.

          When you’ve spent years being responsible for everything, stepping back doesn’t always come naturally. You know the customers, understand the products and can anticipate problems before they happen. Sometimes doing something yourself feels easier than explaining it to someone else.

          So you keep doing it. The business grows, but your responsibilities grow with it. More customers, more staff, more decisions requiring your approval. Before long, you may find that you’ve built a business that struggles to function unless you’re constantly available.

          Sometimes, the very things that make you feel indispensable are the things preventing your business from growing beyond you.

          Working in your business versus working on your business

          There’s a difference between working in your business and working on your business.

          Working in the business means attending to its daily demands: customers, orders, complaints, staff, deliveries and approvals. Working on the business means developing people, improving processes, building systems and planning for the future.

          Both matter. But daily operations can consume every available hour. You finish the day exhausted, having solved one problem after another. You’ve worked hard, certainly. But have you made the business any less dependent on you?

          Learning to let go

          I think one of the first things founders must remember is that your business was never about you. It was always about the people you set out to serve.

          You may have started it and invested years of your life into building it, but customers should be able to receive the quality of products and services you promised, whether you’re personally attending to them or not.

          Making that possible requires investing in people.

          You cannot build a business alone. And you don’t always need everyone to arrive fully formed.

          Sometimes you have to build with the people you have while helping them become the people the business needs.

          Train them, share your knowledge and give them responsibilities. It may take longer initially to teach someone than to do the work yourself, but if you never make that investment, you may be doing the same task for years.

          Then comes the harder part: learning to let go.

          If you wait until someone can do everything exactly as you would, you may never delegate anything.

          And even after delegating, you must learn to look away.

          We sometimes give people responsibility, then spend the entire time watching, correcting and interfering. We want them to take ownership, but we also want everything done precisely our way. Not everything will be done your way. And sometimes, somebody else’s approach might even be better.

          Set expectations, provide guidance and check the results. But give people room to think, make decisions and grow.

          You can hold people accountable without controlling every step they take.

          And while you’re learning to let go, document what matters.

          Because if every process, instruction and standard lives in your head, then you’re still the system.

          Create procedures, checklists and clear expectations so people have something to refer to without constantly needing you to explain what comes next.

          Giving your business wings doesn’t mean leaving it behind

          Not every founder wants to build a large company, expand into new markets or employ hundreds of people. Some people genuinely want to keep their businesses small, familiar and manageable. And there’s nothing wrong with that. But even a small business doesn’t have to require you to carry everything yourself.

          Personally, there are parts of running a business that I genuinely value, and I don’t think I should have to give them up simply because I’m the founder.

          There's a difference between being involved because you want to be and being involved because nothing can function without you.

          You should be able to remain close to your customers, care deeply about your products and stay involved in what matters to you, without being responsible for every little thing.

          We often measure business growth by revenue, customers, employees or locations. But perhaps another measure is whether the business can continue delivering on its promises when you’re not in the room.

          Because you can spend years building a business, only to discover that you’ve also built yourself a job you can never leave.

          Your business is like your child. You nurture it, invest in it and give it everything you can. But you must also give it wings.

          Are you building a business that can stand on its own, or one that will always need you to hold its hand?

          Until the next note,

          – STB

          Notes with STB | A content series exploring mindset, money and business.


          The Brief Network: Inspiring Stories and Empowering Lessons.

          Edward Moshole Went from Being a Factory Cleaner to Building a Manufacturing Business

          Edward Moshole started with R68, selling cleaning products to fellow workers at a food processing factory in South Africa. Years later, he would build Chem-Fresh, a detergent manufacturing business whose products reached major retail chains.

          His story began in 1999 when he recognised an opportunity in the demand for cleaning products. Rather than invest in manufacturing immediately, he started by buying and reselling existing products, using his wages to purchase his first stock.

          He bought a five-litre bottle of bleach and sold it by the litre, starting with colleagues who needed cleaning products but often had limited time to shop. From there, he expanded to door-to-door sales, households and local shops.

          Moshole eventually wanted to do more than resell other companies’ products. He began experimenting with detergent production in his backyard, using second-hand 25-litre spice drums and a homemade manual mixer. He spent weekends learning how to manufacture the products, gradually developing the skills needed to establish his own brand.

          This led to the creation of Chem-Fresh, which produced detergents and disinfectants. The move into manufacturing gave him greater control over his products and opened up opportunities to grow beyond small-scale sales.

          In 2004, Moshole left his job to focus on the business full-time. His next goal was to get Chem-Fresh products into major retail outlets, particularly Pick n Pay. Securing a place on supermarket shelves was difficult, but he continued pursuing the opportunity.

          Chem-Fresh eventually entered Pick n Pay’s retail market in 2007. To meet growing demand, the business needed to increase its production capacity. Support received through South Africa’s Technology Transfer Fund in 2006 helped the company acquire mixing and filling equipment and raw materials.

          These improvements reportedly increased its production capacity from around 200 litres of dishwashing liquid a day to as much as eight tonnes a day. Chem-Fresh went on to expand its product range and supply other major retailers, including Spar, Massmart and Dis-Chem.

          Moshole’s experience shows that building a business often requires several stages of growth. Reselling gave him a way to enter the market, manufacturing allowed him to develop his own products, and improved equipment helped him meet the demands of larger customers.

          His story also highlights the value of starting with a manageable opportunity. He began with people he already knew, expanded his customer base and gradually developed the skills and resources required to grow.

          An opportunity becomes meaningful when you take the steps to turn it into something real.

          His journey teaches us that opportunities can exist in places we already know. The work we do and the needs we observe can reveal possibilities worth exploring. However, recognising an opportunity is only the beginning. Turning it into a sustainable business requires learning, reinvestment and the willingness to adapt as the business grows.

          Edward Moshole’s rise from factory cleaner to business owner was built through practical decisions made over time. His story reminds us that a modest beginning can become the foundation for something greater when initiative is matched with consistent effort and a willingness to learn.

          The Brief Network: Inspiring Stories and Empowering Lessons.

          Isaac Sesi Saw a Problem in Agriculture and Built a Business Around It

          Agricultural losses do not always happen in the field. Grain that has been harvested can still be damaged during storage if it contains too much moisture. For farmers, this can mean losing produce they have already spent time and money growing.

          In Ghana, this problem presented an opportunity for Isaac Sesi, an electrical engineer who was working as a research engineer at Kwame Nkrumah University of Science and Technology (KNUST).

          His work on a grain moisture meter led to the development of GrainMate, a device designed to help farmers measure the moisture content of their grain before storage. In 2018, he founded Sesi Technologies to take the product beyond university research and into the market.

          The decision marked the beginning of a business that would have to contend with the realities of manufacturing, financing and getting farmers to adopt a new technology.

          From Research to a Commercial Product

          Before GrainMate became a commercial product, it was a research project aimed at addressing post-harvest losses.

          Sesi was part of a team working to develop an affordable grain moisture meter that could be manufactured locally. The need was practical. Some farmers estimated moisture levels by biting or tossing grains because suitable measuring equipment was expensive or difficult to access. These methods could lead to inaccurate assessments and unsafe storage conditions.

          GrainMate offered a more reliable way to measure moisture content in grain, helping farmers make informed decisions before storing their produce.

          For Sesi, the project presented an opportunity to put engineering research to practical use. 

          “I decided this project wasn’t going to end as another academic project.”

          He established Sesi Technologies in March 2018 to commercialise the technology. The decision meant taking responsibility for more than developing a working device. The company also had to manufacture it, find customers and establish a way to generate revenue from its sales.

          The Cost of Taking Technology to Market

          Building the product was one challenge. Financing its production was another.

          Reflecting on the company’s early financial difficulties, Sesi said:

          “We started with no money, absolutely no money.”

          The company secured pre-orders from a customer who paid 70 per cent upfront, allowing the team to finance the initial inventory needed to fulfil the order. This arrangement helped Sesi Technologies move forward without having all the production capital available at the outset.

          It also illustrates a practical difficulty for hardware businesses: a product may have a willing customer, but the company still needs money to manufacture and deliver it.

          The team faced other challenges. In his account of the company’s early years, Sesi acknowledged that they had limited experience in electronics manufacturing, set unrealistic production timelines and overpromised to clients. He also wrote about becoming distracted by pursuing too many activities and nearly running out of cash several times.

          These problems affected the company’s ability to manage production and meet its commitments. They were reminders that developing a useful product does not automatically create a well-run business.

          The Question of Scaling

          In 2019, Sesi Technologies was producing a few hundred GrainMate units every couple of months at its facility in Kumasi. During a conversation with an investor, Sesi was asked a question that challenged his growth plans:

          “What’s your plan to scale from 200 units to 200,000 units?”

          Until then, he had focused on refining the product and fulfilling orders. Scaling, however, required a broader plan for manufacturing, supply chains, logistics and distribution. Selling more units would mean little without the capacity to produce and deliver them reliably.

          Having a product that solves a problem is only the beginning. Building the capacity to deliver it at scale is what turns an innovation into a sustainable business.

          Sesi Technologies later expanded beyond GrainMate into post-harvest services, including drying, threshing, storage and market access. The company also developed FarmSense, a soil intelligence solution designed to help farmers make informed decisions about soil conditions and crop production.

          In 2019, Sesi was named one of MIT Technology Review’s Innovators Under 35 for his work in agricultural technology.

          His experience highlights a key challenge for entrepreneurs: developing a useful product is one achievement; building a business that can deliver it consistently and grow sustainably is another.

          The Business Behind the Technology

          Isaac Sesi’s experience with GrainMate demonstrates the work involved in turning an engineering solution into a commercial enterprise. Identifying a problem and developing a useful product are important first steps, but manufacturing, financing, customer relationships and planning for growth determine how effectively that solution can reach the market.

          For entrepreneurs, the central takeaway is straightforward: solving a problem creates an opportunity, but building a sustainable business requires a plan for delivering that solution consistently.


          The Brief Network: Inspiring Stories and Empowering Lessons.

          Persistence Is More Than a Mindset. It’s a Numbers Game

          Here is something motivational content rarely talks about: persistence has a mathematical side.

          We are often told to keep going, believe in ourselves and never give up. But beyond determination, there is a practical reason to keep trying.

          The more opportunities you give yourself to succeed, the less your future depends on the outcome of any single attempt.

          Let’s do a simple probability exercise: If you have a 10% chance of succeeding on any one attempt, your probability of succeeding at least once across five independent attempts is approximately 41%. Across ten attempts, it rises to 65%.

          The odds of each individual attempt haven’t changed. What has changed is the number of opportunities you’ve given yourself. Of course, real life is more complicated, but the principle is worth thinking about.

          You approach one or two potential customers. They say no. You conclude there is no market for your product. You apply for a job. When you don’t get it. You may think you’re not qualified. You pitch an investor. When they decline. Suddenly, you’re questioning the entire business. The truth is one rejection is a very small sample from which to draw conclusions about your future.

          Sometimes, you just haven’t knocked on enough doors.

          Before J.K. Rowling’s Harry Potter and the Philosopher’s Stone was published (I wrote about this in the Invisible Season), twelve publishers had rejected the manuscript. Bloomsbury eventually said yes.

          Imagine if she had stopped at the third rejection.

          We know the ending now, so persistence looks like an obvious choice. But Rowling didn’t know that the next publisher would say yes.

          And that is the uncomfortable thing about persistence. You often have to keep trying without knowing whether the next attempt will change anything.

          Not every rejection means the idea is bad. Sometimes it’s the wrong audience, the wrong timing or simply the wrong person making the decision.

          But trying again should also make you wiser.

          A 2010 study published in the Journal of Financial Economics found that entrepreneurs who had previously built a successful venture had a 30% chance of succeeding in their next one, compared with 21% for first-time entrepreneurs. The study examined venture-capital-backed businesses and measured success by whether a company went public.

          That doesn’t mean every attempt makes you more successful. But experience can improve how we recognise opportunities, assess risks and make decisions.

          Your tenth pitch shouldn’t necessarily be identical to your first. By then, you should have learnt something about your audience, your offer or your approach.

          Persistence without learning can become repetition. Persistence with learning can become progress.

          And sometimes, the evidence will tell you to change direction or stop altogether. There is wisdom in knowing when an idea is no longer worth pursuing.

          Don’t turn one rejection into a lifetime verdict.

          We should not treat a disappointing outcome as a final assessment of our ability, when it may only tell us what happened in one particular situation. One customer said no. One application was unsuccessful. One idea didn’t work.

          What have you learnt? What could you do differently? And have you tried enough to make an informed decision?

          Because there is a difference between something that has failed after a fair test and something that has barely been given a chance.

          Rejection is not always a verdict. Sometimes, it is data.

          So before you conclude that something cannot work, ask yourself:
          Have I really tested this idea?
          Have I learnt anything from the attempts I’ve made?
          And most importantly, have I given it enough of a chance to know?

          Because sometimes, what looks like failure is simply a conclusion reached too early.

          Until the next note,

          – STB

          Notes with STB | A content series exploring mindset, money and business.

          Research reference: Gompers, P., Kovner, A., Lerner, J. & Scharfstein, D. (2010). Performance Persistence in Entrepreneurship. Journal of Financial Economics, 96(1), 18–32.


          The Brief Network: Inspiring Stories and Empowering Lessons.

          Eleven Rejections, One Dream: José Hernández’s Road to Space

          José Hernández went from picking crops in California’s agricultural fields to looking back at Earth from space. Born into a Mexican migrant farmworking family, he grew up moving between farms as his parents followed seasonal work. Years later, after earning degrees in engineering, contributing to scientific research and facing eleven rejections from NASA, he finally earned a place among the astronauts aboard Space Shuttle Discovery.

          His achievement was remarkable, but the years that led to it make his story even more compelling. Hernández had to turn a childhood ambition into a practical plan, build the qualifications to pursue it and keep improving after repeated disappointment. His experience shows what sustained effort can look like when a goal demands far more than enthusiasm alone.

          A Childhood Spent Following the Harvest

          Hernández spent his early years moving around California as his family followed seasonal agricultural work. As a child, he helped pick crops such as strawberries and cucumbers while balancing school with the demands of farmwork. He did not learn to speak English until he was 12.

          His circumstances were a long way from the world of space exploration. Yet, an experience in 1972 would introduce him to a possibility that stayed with him for years.

          That year, he watched television coverage of the Apollo 17 Moon mission with his family. Seeing astronauts travel beyond Earth made a lasting impression on him. What began as childhood fascination gradually developed into an ambition he would carry into adulthood.

          Having a dream, however, was only the beginning. He would need an education, technical knowledge and years of preparation to give that ambition a realistic chance.

          Turning an Ambition into a Plan

          Hernández pursued electrical engineering at the University of the Pacific in California before earning a master’s degree in electrical and computer engineering from the University of California, Santa Barbara.

          He went on to work at Lawrence Livermore National Laboratory, where his research included technologies related to X-ray lasers and the development of digital mammography systems used to support early breast cancer detection.

          These achievements reveal an important part of his story. While pursuing his ambition of becoming an astronaut, Hernández was already building a career in science and engineering, gaining experience and contributing to important research.

          He was not waiting for his dream to come true before taking his next step.

          He was building the knowledge and experience that could bring him closer to it. Each stage of his education and career gave him skills he could draw on as he continued pursuing his goal.

          Ambition gives a person somewhere to go, but preparation helps make the destination possible.

          Eleven Rejections, but No Final Answer

          Hernández applied to NASA’s astronaut programme and was rejected eleven times before he was selected on his twelfth attempt in 2004.

          For anyone pursuing a difficult goal, eleven rejections might seem like a clear signal to stop. For Hernández, however, each unsuccessful application became an opportunity to examine what he could improve.

          He studied the backgrounds of astronauts who had been selected and identified skills he could develop. He earned a pilot’s licence, obtained scuba-diving qualifications and expanded his experience. He also learned Russian, a useful skill for working in international space operations.

          His approach was practical. Instead of treating rejection as proof that he could never succeed, he looked for ways to strengthen his candidacy.

          Eleven rejections did not end his pursuit. They gave him reasons to prepare differently.

          This does not mean that persistence guarantees success or that every rejected opportunity is worth pursuing indefinitely. It means that, when a goal remains important and achievable, a setback can provide information that helps a person make a better attempt.

          Hernández’s experience shows that perseverance is more than repeating the same action. Sometimes, it means changing your approach, developing new skills and becoming better prepared for the next opportunity.

          The Day the Dream Became Reality

          In 2004, NASA selected Hernández as part of its nineteenth astronaut class. He completed astronaut training and, in August 2009, travelled into space aboard Space Shuttle Discovery on mission STS-128.

          The mission took the crew to the International Space Station, where they delivered supplies and equipment and supported the station’s continuing operations.

          For Hernández, the flight represented the culmination of a childhood ambition that had survived years of preparation and repeated disappointment. The journey from working in agricultural fields to orbiting Earth was extraordinary, but it was not a sudden leap from one life to another.

          It was the result of education, professional experience, deliberate preparation and a willingness to keep improving after rejection.

          His achievement also carried a wider message for young people who may struggle to imagine themselves in fields where they rarely see people with backgrounds like theirs. A person’s beginnings do not have to determine the full extent of their ambitions.

          The Work Behind the Dream

          Hernández’s story offers several ideas worth carrying into everyday life.

          First, take your ambitions seriously enough to prepare for them. Wanting a particular career or outcome is a starting point. Learning the necessary skills, seeking experience and understanding the demands of the opportunity are what help turn that ambition into a plan.

          Second, let rejection prompt reflection. Disappointment is real, and not every setback has an obvious solution. But it is worth asking what an experience can teach you, what needs to change and whether another attempt makes sense.

          Third, invest in skills beyond the minimum requirement. Hernández did not rely on his engineering qualifications alone. He continued developing abilities that could strengthen his application. In any field, a willingness to keep learning can open possibilities that were previously out of reach.

          Finally, recognise that progress can happen before the final breakthrough. Hernández was already building a meaningful career in engineering before NASA selected him. The years spent gaining knowledge and contributing to scientific research were not wasted simply because he had not yet reached space.

          Ambition gives a person somewhere to go, but preparation helps make the destination possible.

          His story encourages us to value the person we are becoming while working towards the goal we hope to achieve.

          Hernández’s remarkable journey also inspired A Million Miles Away, a 2023 biographical film starring Michael Peña. The film brings his experiences to the screen, from his childhood in a migrant farmworking family to his eventual achievement as a NASA astronaut. It offers another way to encounter a story shaped by ambition, preparation and persistence.

          A Dream Worth Preparing For

          José Hernández’s journey from migrant farmworker to NASA astronaut was built on years of learning, preparation and persistence. After eleven rejections, he did more than hope for a different outcome. He worked to become a stronger candidate.

          Not every ambition will unfold as planned, and some goals may require a different path. But Hernández’s story reminds us that rejection does not have to be the end of the road.

          Ultimately, the distance between where we begin and where we hope to be is bridged by the work we put in when no one is watching.

          The Brief Network: Inspiring Stories and Empowering Lessons.

          From Laying Bricks at 13 to Building a Real Estate Business: Lessons from Ayobami Akindipe

          At 13, Ayobami Akindipe worked as a bricklayer. By 21, he had become a licensed real estate agent. In 2019, he founded ACE Real Estate Development, marking his transition from construction and property sales into real estate entrepreneurship.

          His journey offers valuable insights into recognising opportunities, building on practical experience and taking calculated risks to grow a business. From his early days in construction to leading a property development company, Akindipe’s story highlights the decisions and skills required to turn industry experience into a business venture.

          1. Start with the Opportunity You Can Access

          Akindipe’s entry into the construction industry was through bricklaying, not property investment or development. His journey shows that entering an industry at an operational level can provide a starting point for exploring other opportunities within it.

          His experience also challenges the assumption that entrepreneurship must begin with substantial capital. Understanding how an industry works can be a valuable first step towards identifying where you can contribute and grow.

          What founders can learn: Start with the opportunities available to you. Understand the industry, identify its gaps and build the knowledge needed to progress into more valuable roles.

          2. Build on What You Already Know

          By 21, Akindipe had become a licensed real estate agent, moving from construction work into property transactions. This was a shift in both his responsibilities and the skills required to succeed.

          Rather than remaining in one role, he moved into another part of the industry. His progression highlights the value of understanding how different activities within a market connect.

          What founders can learn: Before pursuing an entirely new industry, examine the opportunities within the one you already understand. Your existing experience may give you a useful starting advantage.

          3. Understand What Growth Demands

          When Akindipe founded ACE Real Estate Development in 2019, he moved towards building a business that extended beyond property agency. The company’s subsequent expansion into residential development involved a different level of responsibility.

          Property development requires more than identifying buyers and sellers. It involves managing resources, coordinating projects and ensuring that properties are delivered as expected.

          “Growth is not just about taking on bigger opportunities; it is about building the capacity to deliver on them.”

          What founders can learn: Before expanding, assess whether you have the capital, expertise, systems and partnerships needed to support the next stage of your business.

          4. Back Your Ambition with Financial Discipline

          Akindipe’s early business journey reportedly involved selling personal properties to commit more fully to ACE Real Estate. This illustrates the financial commitment that building a company can demand.

          However, personal sacrifice alone does not guarantee success. Founders must understand the risks involved and make deliberate decisions about how much they can afford to invest.

          What founders can learn: Match your financial commitment to a clear business plan. Assess the costs, risks and potential returns before putting personal assets into your venture.

          5. Turn Your Expertise into Opportunities for Others

          Through ACE Academy, Akindipe extended his involvement in real estate beyond property transactions and development. The initiative was established to train and mentor young Nigerians interested in real estate sales and related opportunities.

          This demonstrates how industry knowledge can become valuable beyond the founder’s own business. Training can help people develop relevant skills and find entry points into a market that may otherwise seem inaccessible.

          What founders can learn: Identify what your business knows how to do well and consider how that expertise can solve another problem, develop talent or create opportunities for others.

          6. Build a Business That Can Operate Beyond You

          Expanding into property development increases the demands on a business. Projects require coordination, cost management, quality control and consistent customer communication.

          A founder’s personal experience may help establish a company, but long-term growth depends on whether the business can deliver consistently as its operations become more complex.

          What founders can learn: Document processes, delegate responsibilities and establish measurable performance standards. Build systems that allow the business to grow without depending on your involvement in every decision.

          Final Thoughts: Turn Experience into Enterprise

          Ayobami Akindipe’s journey from bricklaying to real estate entrepreneurship illustrates how practical experience can become a foundation for business development. His progression highlights the importance of understanding an industry, building on existing skills, managing financial risks and developing the capacity to deliver at a larger scale.

          For aspiring founders, the central takeaway is clear: knowing how to do the work is a starting point; building a business requires learning how to create, deliver and sustain value.

          The Brief Network: Inspiring Stories and Empowering Lessons.