5 Questions Every Entrepreneur Should Be Asking Right Now
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Jenn Wint, PR expert and small business coach, shares her Top 5 Questions Every Entrepreneur Should be Asking Right Now
Join Jenn Wint, Rachel Quinn, and 8 small business experts at Back to Business on September 16th.
Top 5 Questions Every Entrepreneur Should be Asking Right Now
Entrepreneurs and small business owners wear many (many, many) hats. We’re the CEO, the marketing director, customer service rep, bookkeeper, caterer, event planner, social media manager, hardware mechanic and the list goes on. It’s part of the thrill but it can also be overwhelming. Most of us started our businesses because we wanted to focus on the thing we’re passionate about, not because we wanted to send invoices or spend hours lost in the back-end of Wordpress.
We know we need support with parts of our business. But we’re busy, really busy, and we aren’t sure where to find the best advice. As we enter Q4 and the home stretch of 2025, now is the perfect time to pause, reflect and get the advice needed to finish the year strong.
Here are five essential questions every entrepreneur should be asking themselves right now. If you don’t have clear answers, consider this your invitation to connect with some experts (more about that at the end) and to make some intentional shifts before the year wraps.
1. Are my 2025 finances in order?
Many entrepreneurs fly by the seat of their financial pants. Maybe you’re focused on generating revenue, and that’s going well but do you know how your money is flowing in and out? Do you have systems in place for budgeting, forecasting, saving, and paying yourself?
Ask yourself:
Do I have a financial plan for Q4 and beyond?
Am I tracking expenses and understanding profit margins?
Have I set aside money for taxes?
Am I charging the right amount for my services?
If your books are messy or you don’t have clarity on your cash flow, those excel spreadsheets are worth looking at. Financial clarity is the foundation for confident decision-making and sustainable growth.
2. Should I incorporate my business?
This is a big one. If you’re still operating as a sole proprietor, you may be wondering if it’s time to level up. Incorporating can offer tax advantages, protect your personal assets, and give your business more credibility.
But it’s not for everyone. Incorporating comes with more administrative responsibilities, so you’ll want to weigh the pros and cons based on your income level, industry, and goals.
Some questions to ask:
Am I making enough revenue to justify incorporation?
Could I benefit from corporate tax rates or income splitting?
Do I need legal protection from liability?
Am I prepared to take on the reporting obligations?
If you’re unsure, chat with an accountant or legal advisor who can walk you through the options (incorporation, partnership, LLC, etc.) and help you decide what’s best for your situation.
3. Is my website optimized for SEO?
Your website is often the first impression of your business but it’s also your biggest missed opportunity if it isn’t showing up in search results. SEO (Search Engine Optimization) helps people find you when they’re looking for exactly what you offer.
Quick SEO check:
Does my website have relevant keywords my audience is actually searching?
Are my page titles and meta descriptions written strategically?
Is my site mobile-friendly and fast to load?
Am I consistently adding new, valuable content?
What are back links and how can I get some?
If you don’t know the answer to these, you’re likely missing out on organic traffic and customers. SEO is fixable when you know what to do. Start by updating your website copy with clear, specific keywords and focus on content that helps your ideal client solve problems.
4. Is it time for a brand refresh?
Your brand is more than your logo, it’s the experience people have with your business and often your first impression. It’s also colours, font and vibe. Does your brand feel current, consistent, and aligned with your audience’s needs and values? Or is it feeling a little tired?
Try asking:
Am I proud to hand out my business card?
Are my visuals (styles, fonts, imagery) still reflective of what I do?
Do my clients see themselves in my messaging?
Has my business evolved beyond my original brand?
If your brand no longer reflects your mission or audience, it might be time for something new. A brand refresh doesn’t have to mean starting from scratch, it can involve tweaks that elevate your presence so you can show up with confidence and attract the right people.
5. How can I systemize and organize to avoid burnout?
Balancing every role in your business isn’t just exhausting, it’s unsustainable. Hustle culture still lingers but smart entrepreneurs know that systems and sustainability beat burnout every time.
Consider:
What tasks am I doing repeatedly that could be automated or outsourced?
Do I have systems for onboarding clients, delivering services, and managing projects?
Where am I spending time that’s not aligned with revenue?
Where can I schedule rest and how can I ensure I take that time?
Burnout is one of the biggest threats to small business owners. Creating systems, even simple ones like checklists, templates, and automated emails, can free up mental space and allow you to focus on what matters.
Treat Yourself to a Day with the Experts and get Back to Business
Back to Business: September 16th
No one has all the answers. But knowing the questions can give you clarity and the insight you need to take your next right step, whether that’s organising that wad of receipts, updating your website, incorporating your business or building systems that protect your time and energy.
If you’re ready to finish the year with purpose, join us at Back to Business, a one-day intensive event designed to help entrepreneurs close out 2025 with clarity, strategy, and confidence.
You’ll connect with a focused group of small business owners and gain personalized, 1-to-1 insight from eight experts in key areas like SEO, branding, accounting, legal compliance, and public relations through targeted 30-minute micro-meetings.
Back to Business will give you the tools and support you need to end 2025 strong. It’s also going to be a really fun and inspiring day full of awesome people, cool ideas and great networking in the beautiful Vessel Designs event and co-work space.
Join us September 16 for a full day of inspiration, growth and connection.
Back to Business is proudly sponsored by Vessel Designs
The Vessel Events and Community Space is ideal for anyone seeking a welcoming homebase in which to foster community and build meaningful connections. If you host in-person gatherings of any size and would benefit from adaptable, reasonably priced spaces, we warmly encourage you to come in for a tour.