The hardest thing about being an entrepreneur is carrying every decision alone. Knowing when, and who, to ask for help is a skill in its own right, and one most first-time entrepreneurs learn the hard way.
Why entrepreneurs struggle to ask for help
Many entrepreneurs come from a corporate background with a broad safety net of established cash flow and support structures, and are genuinely new to the reality of running their own cash flow. The tough calls, whether to buy a business to kick-start growth, whether to spend scarce capital on ads or on hiring an agency, why it’s so hard to charge full price for your own services, all land on one person’s desk with no one to run them past.
Where group coaching helps
A group coaching setup with other entrepreneurs can change the outcome of a genuinely difficult call. Walking away from a deal that looked good on paper but didn’t fit the underlying vision is a common example, one that’s much easier to see clearly with input from people who understand the pressure you’re under.
Struggling to price your own services?
A common pattern among new entrepreneurs, especially those selling a service built around their own name or expertise, is chronic underpricing. Separating “you the product” from “you the person” is a genuinely hard psychological shift, and a coach who has seen the pattern before can help you make it faster than working it out alone.
How do I know which kind of support I need?
- A business or financial coach paid by the hour is usually the right starting point if you don’t already have a relationship with a financial adviser, since they help you understand the choices available and provide knowledge to support your own decisions.
- A financial adviser becomes more relevant once you’re generating consistent profit and are ready to plan further ahead, for your business and your own finances.
- Group coaching or a mastermind works well when you want to learn from other entrepreneurs’ experience as well as an expert facilitator’s input.
Fit matters as much as credentials, it’s worth speaking to more than one coach or adviser before committing to work with someone.
When should you actually seek help?
- When you’re stuck on a decision and can’t get past the noise in your own head.
- When you don’t have enough information to make the call confidently.
- When you notice a pattern of thinking or behaviour that isn’t serving you or your business, at the extreme, genuine self-sabotage.
- When you and a business or life partner can’t productively discuss a financial decision affecting the business.
Frequently asked questions
Should a first-time entrepreneur see a financial coach or a financial adviser?
Usually a financial coach first, particularly while you’re still making foundational decisions about how to use limited capital. A financial adviser becomes more relevant once the business is generating consistent profit.
How do I know if a specific coach is the right fit for me?
Chemistry and shared experience matter as much as formal credentials. It’s reasonable to speak with a few different coaches before choosing one to work with.
What are the clearest signs I need outside help with a business decision?
Being stuck on a decision, lacking the information to make it confidently, noticing a self-defeating pattern, or being unable to align with a business or life partner on a financial call are all strong signals.
Is group coaching a substitute for one-on-one advice?
Not entirely, but it adds genuine value by exposing you to other entrepreneurs’ experience alongside an expert facilitator’s input, which one-on-one coaching alone doesn’t offer.
Carrying the load with support, not alone
Every entrepreneur eventually hits a decision too big to make alone. Recognising that moment early, and knowing which kind of support actually fits it, tends to separate businesses that recover from a hard call from ones that don’t.
By Lisa Linfield, a board Certified Financial Planner and CEO of Southern Pride Wealth, and host of the podcast Working Women’s Wealth.
Originally published in January 2020. Updated September 2026 to refresh this guest financial-coaching advice for entrepreneurs. The underlying decision-making guidance here is durable and not tied to a specific period.
