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From Self‑Doubt to Self‑Assurance: How First‑Time Business Owners Build Confidence

Wicus Van Biljon

14-01-26

1.Introduction: Why Confidence Matters in Business

Starting your first business is thrilling, but it can also be nerve‑racking. When you’re navigating everything from marketing to money on your own, self‑doubt often creeps in. Confidence isn’t just “feeling good”; it’s a crucial part of making decisions, the resilience to stick with your goals, and the courage to step outside your comfort zone.

As WomanWho.co.uk puts it: “Having confidence in your professional abilities allows you to push yourself, step out of those comfort zones, and achieve success.”

Whether you’re pitching clients, setting prices, or hiring help, confidence helps you act, not second‑guess yourself.

2.Why Leading Can Be Lonely

Being a solo entrepreneur has incredible freedom, but it also means you hold all the reins. There’s no partner to share worries, no manager above you to endorse a decision, and no team of advisors you can check ideas with every morning.

As Matthew Levington, Co‑Founder of Business Doctors, says: “It’s not easy for individuals who have built up a business single‑handedly to open up to others about their concerns.”

That feeling of isolation makes self‑doubt louder. Without sounding boards, you might question your choices more often, even when you’re doing well.

3.How Confident Are You Feeling Right Now?

Before building confidence, it helps to understand where you are. Take a moment to rate yourself (0 = low confidence, 5 = very confident).

Decision making

How comfortable are you making strategic decisions (even when the outcome isn’t certain)?

Finances

Do you feel solid about your pricing, cash flow, VAT/tax, and budgeting?

Networking and Support

Are you comfortable reaching out to others -peers, clients, or mentors?

Resilience and mindset

When things go wrong, do you bounce back or spiral?

Be honest: identifying where your confidence is lowest helps you focus on where you need growth.

4.Practical Strategies for Building Confidence

Confidence isn’t something you’re born with; it’s something you build. Here are practical ways to get there:

Embrace Planning

Clear plans don’t guarantee success, but they dramatically reduce overwhelm.

When you break big goals into small, achievable tasks, you build belief through achievement.

Planning also gives you a map on unclear days, and that reduces fear.

Use Data to Empower Decisions

“Guesswork feeds doubt, data feeds confidence”, Business Doctor Steve Jebson

Track key numbers such as sales trends, customer retention, website clicks, or ad performance. When you see what’s working (or not), decisions become choices backed by evidence, not hunches.

Connect with Mentors and Peers

Speaking with those who’ve had similar experiences can boost your confidence.  Mentors and peers offer perspective, encouragement, and real‑world advice.

Here are a few ways to find that support:

  • Reach out to respected local business owners you admire.
  • Join a reputable mentoring group or community.
  • Attend networking events and check online business directories.
  • Explore formal mentor‑match programs or small‑business hubs.

Even a couple of supportive conversations each month can sharpen your thinking and quiet your doubts.

Keep Learning

Confidence grows when you feel equipped. That doesn’t mean going back to school, it means small, targeted learning:

  • Read short guides on finance basics.
  • Join a workshop on marketing.
  • Listen to podcasts about business growth.

Every new skill builds your belief in your abilities and your comfort with challenges you’ll meet.

5.Why It Helps to Speak to Others Going Through the Same

Talking openly with business peers or mentors does more than offer advice; it builds a sense of belonging and reduces the feeling that you’re “figuring it all out alone.” Just having someone to voice a worry to can be therapeutic. And the numbers back up the value of mentorship: research shows that 66% of UK business owners say mentoring was crucial to their survival, and 76% report it supported business growth. (UK Business Mentoring)

Joining a peer-to-peer leadership group, like One by Uspire, can provide that consistent, structured space to share ideas, overcome challenges, and grow in confidence alongside others who truly understand the journey.

6.Mentorship: A Powerful Boost for Confidence

Mentorship is not the same as coaching or training; it’s a relationship with someone who has lived through business challenges and can help you avoid common pitfalls.

Here’s how the roles differ:

Mentor

Coach

Focuses on long‑term growth Focuses on short‑term
goals
Shares experience and context Uses methods to guide actions
Offers advice based on past challenges Helps unlock your own insights

Research shows that mentoring has a real impact for UK small businesses with 66% of business owners reporting that mentoring was crucial to their survival, and 76% saying it played a key role in business growth. Many also report improvements in leadership skills, strategy and turnover as a result of mentoring support. UKBM

A great mentor does more than give answers; they help you clarify your thinking, as one insight suggests:

“A good business mentor… helps you confirm, abandon, or shape some of your own business instincts.” The Portfolio Collective

And as Shopify says: “An experienced mentor helps you find your best self, faster than time alone would allow.”

That doesn’t just make decisions easier, it makes you feel more confident making them.

What You Should Look for in a Mentor

Not all mentors are the same. When choosing one, look for these traits:

  • Great listener: someone who truly hears your challenges.
  • Genuine and trustworthy: you should feel safe being open with them.
  • Passionate about helping others: mentoring should feel energising, not transactional.
  • Proven success: they’ve built or led real businesses and can show results.

Your mentor doesn’t have to be a celebrity CEO; the best ones are often experienced business owners who understand your questions and goals.

Putting Your Trust in a Mentor

It’s common to hesitate before opening up to someone, especially when you’re used to handling everything yourself. But mentorship isn’t about judgment – it’s about support. A good mentor will put your mind at ease straight away, help you sift through ideas, test assumptions, and build confidence from real progress. Confidence doesn’t suddenly appear – it grows as you take action, measure results, learn from experience, and connect with others who understand your journey.

8.Why doing nothing is the riskiest move

If you’re feeling stuck, it’s worth asking yourself: what’s the cost of staying where you are? From my experience working with business owners, people don’t change because a new strategy sounds helpful, they change when standing still starts to hurt. When confidence is low, indecision creeps in, opportunities pass by, and momentum stalls. Doing nothing can feel like the safe option, but in truth, it’s the riskiest move of all. Businesses that wait too long to act often find themselves reacting to problems instead of steering towards solutions. The discomfort of change is temporary but staying stuck is what really drains your energy and potential.

If you want to unlock your confidence and grow your business, you don’t have to do it all alone, one conversation with a mentor could make all the difference. If you would like to talk with a Business Doctor, please get in touch.

Other articles on the subject:

Should you work with a mentor

What is a business mentor

Top tips for finding a business mentor

 

Author: Wicus Van Biljon

I'm well aware of the challenges facing SMEs today, and what it's like to be caught in the owner's trap.

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