23 Questions That Will Help You Decide Which Business to Start

These might change YOUR ENTIRE FUTURE, no exaggeration

Ever been high?

I don’t mean high high, I mean high on a new business idea. 💡 There is nothing like being high on the possibility of new. (Except maybe being high on the possibility of pasta. 🍝)

But then you stall because you realize it’s kind of a big undertaking, and is it maybe too big? Can you commit to this thing, before it’s making you any money? Do you have what it takes to make this into a bonafide thing? (Or is it just going to be “another one of your grand ideas that fizzled out?”).

^^^ I hear this all the time from ambitious people who start things and then don’t finish them and then feel like something is wrong with them. But I think these people have a hidden talent: it takes courage to change directions when you know something’s not right. Do you know how many people keep going with their torturous, unbearable lives, despite knowing it’s not right???

The truth is, starting something new can be A LOT of fun. But, it can also be paralyzing when you have to make 100 different decisions to get started. (And trust in your ability to make them.) So with that in mind, I’m sharing a list of twenty-three little-asked, but deeply-necessary questions I have personally asked myself to help me sort through my ideas. Not only will these questions help you get clarity, but they will also help give you the confidence you need to step on the gas. Because if there’s anything I have found to be true in business, it’s that a lack of clarity will make you think that your idea is bad, when in fact, it might be great—but just needs some shaping.

Remember: clarity is crack. (And someone should totally steal that brand name. 😆)

So without further ado!

23 Life-Changing Questions to Ask Yourself When Starting a New Business

(That Could Change Your Entire Future, No Exaggeration)

1. Would marketing this be fun for you, or a slog?
   Recently I was in the early stages of creating a fun new brand with an amazing friend and colleague, but when we asked ourselves if we really wanted to talk about this thing every day, we realized we didn’t. And, if you don’t want to talk about your thing, you can’t market your thing. And if you can’t market your thing? Well, good luck. ← THERE IS NO MORE IMPORTANT TRUTH.
   

2. Is this going to bring the kind of people you (actually) LIKE?
   This is crazy but—do you realize how many people don’t actually like their customers? That’s a problem, because people are business. And your enjoyment of your business will always be capped at how much you enjoy the people with whom you do business. Sometimes, however, the solution is a simple repositioning of your idea. If, for example, you’re starting a VA service, do you really want to work with stressed-out executives? Or would you actually love working with a bunch of down-to-earth home contractors who aren’t tech savvy at all and SOOOOO need your help (and would appreciate you forever and ever and ever?)
   

3. Will they nitpick your price or be thrilled to do business?
   This goes back to honing in on clients you want to do business with. The more of a linchpin you are to someone, the happier they are to pay you. So sometimes it’s best to go back to the basics and consider who could really use your services (but doesn’t know jack squat in that department)?
   

4. Is this a fun thing for your customers to be a part of?
   Underrated question! But, um…does the thing you’re building actually sound like fun to people? Or does this sound like a lot of boring, tedious work? (Lookin’ at you, online courses.) I’d ask yourself: how can I make this feel like a fun party???
   

5. How does this help your customers reinforce their identity?
   Not only do people want to be a part of fun, new, exciting things: they also want to be a part of the kinds of things that reflect their core values. I, for example, am much more apt to buy anything that’s sarcastic or witty or irreverent because it reflects my personality and who I am. So, how can your product be a flag in the sand???
   

6. Does the brand rely on you maintaining a certain identity?
   Speaking of identity! Will your brand require you to always be the current version of who you are? For example, if you’re starting a YouTube channel about life in the countryside, you will have to live in the countryside in order for that to work long-term. (That said, it’s also okay to have a 3-year plan and just do what feels right for you now! So long as you won’t feel like a failure when you’ve outgrown it.)
   

7. You’re at a dinner party. Someone asks you what you do. Are you proud and excited to tell them?
   Make sure that what you’re doing is something you actually want to be doing. Do you feel really proud and excited to be a wedding photographer? Or are you slightly embarrassed that this is what you’re doing? If the latter is true, you might do well to consider how you could take your wedding photography (or whatever you do), and turn it into what I call “a research project.” For example, you might not be excited about photographing the 500th best man speech in a row, but what if you decided to start a research project analyzing unspoken wedding etiquette in North America? Now, you’ve got something interesting to talk about, that touches on your new and expanding interests, while still allowing you to keep your existing business? Sometimes, it might not be the work you’ve outgrown, but rather the focus. Try a new focus.
   

8. Does the brand name feel fresh & fun?
   Believe it or not, it makes a *world* of a difference if you LOVE your brand name. This is not a superficial detail! How you craft something affects how people experience it and receive it—including you. If your brand is serious, you’ll feel the pressure to be serious (when in fact, you’d rather be playful). Your brand identity really shapes the way you show up.
   

9. Is it immediately obvious what you do?
   This one is soooo hard because you’re trying to be creative but too often, it’s at the risk of clarity—and the confused mind doesn’t buy. (Fact.) So try to avoid coming up with vague descriptions of your work like “small business wrangler” and “manager of emotions” (or whatever), and instead, put it through the middle school test. In one sentence, could a 6th grader understand what you do?
   

10. Is it expandable? Or does this pigeonhole you?
    “Beth’s Copywriting” is clear, yes, but what if you want to expand to include web design? Ditto for any local businesses thinking about naming themselves “Laguna Beach Tattoos.” If you decide you want to have another studio in New York, your brand won’t make sense.
    

11. Is there a newsworthy / relevant / interesting / fresh angle you can bake into the biz so press and journalists will naturally want to interview you?
    For example, no one’s going to care if you open a pizza shop. There’s nothing newsworthy about that in and of itself (even though it’s big news to you & your family!). That means that the more “standard procedure” your business is, the harder it’s going to be to market. This is why it can be really helpful to consider: what’s an interesting twist I can put on this to make it stand out? For example, Down North Pizza in Philadelphia is a restaurant that employs formerly incarcerated people and aims to reduce employment barriers for them. Do you know how many times this has been covered in the local news, just because of the concept?????????? The right concept will do all the talking.
    

12. What will make your customers want to talk about you?
    Slightly different, focused more on the experience itself. When people buy from you, how can you delight the everloving fuck out of them? Do something that people can’t help but screenshot & share. ←This will take you places.
    

13. Can the people who need to hear it, hear it?
    Are you using your customers’ language? Will your customer know it’s for them? Sometimes it’s easy to use all this professional complicated jargon in an attempt to seem legitimate, but if the person you’re trying to reach doesn’t use that jargon, it isn’t going to resonate. Don’t write for your peers, write for your people.
    

14. What kind of content would be fun to make?
    If you dread making the content, you will dread your entire business. On the other hand, if you can come up with a fun concept that you actually enjoy producing? That passion translates. We can feel that. And, it changes everything. (Especially for you!)
    

15. Does your customer actually use the marketing channels you’re on?
    Worth considering: if you’re the VA who’s decided to market herself to home improvement contractors who have no idea how to “get online” and “do website stuff,” then you will be wasting your time creating a Pinterest board and inviting them to a Discord group. Rather, you’d do well to consider where non-techy people hang out, and how to best reach them. For example, text messages to phone might be more effective than email marketing. (The first time I’ve ever said that!)
    

16. What does your customer need to believe in order to buy from you?
    If the home contractors you’re talking to don’t think they really need to “get online” and “do website stuff,” then they aren’t going to buy it. So, what’s the subset of people who DO recognize the need? And, where are they hanging out?
    

17. Are you presenting yourself as an expert, or an enthusiast?
    I’m just mentioning this because there’s a lot of hesitation around “but I’m not an expert so how can I start that,” but just fyi, you can *totally* start a thing by presenting yourself as an enthusiast. Think of your new project as something you are actively studying, researching, writing about, exploring. Eventually, you WILL be an expert.
    

18. Out of the business models you’re considering, which one is going to feel the most light and simple and joyful? (e.g. a community membership versus a paid newsletter)
    Simple + joyful > complicated + burdensome. That sounds obvious, but how many times have you made things complicated + burdensome because you thought that making it hard was the only way to deserve success?
    

19. Do you really want to build this thing or are you convincing yourself it’s a good idea?
    Gotta ask!
    

20. Is there a path to creating digital products that scale?
    I will never not advocate for digital products. They’re lightweight, they can be delivered to anyone around the world, they help us spread knowledge, and they’re the most scalable product on earth. Not to mention they also give you authority, and your bank account will be bigger than it’s ever been. Make sure to join my new class on this here.
    

21. Will this be exhausting in a way that’s unsustainable or undesirable?
    For example, if you launch with a daily newsletter, you might not realize how much work a daily newsletter is. Can you keep up that pace? Or could you maybe start with a bi-weekly newsletter and see how it goes? It’s better to add things later (and delight your customers), than be forced to subtract them (and make them mad).
    

22. What kind of email do you want to read? Write that newsletter.
    Speaking of newsletters: if you wouldn’t read it, neither will they. So, have fun with it! (Notice a theme here???)
    

23. What if you DID just do the fun thing?
    What if you stopped overthinking it? What if you let your interests guide you? What if your desire to do something was reason enough? What if you actually thought about what would be the most fun thing you could imagine, and then executed on it? I’m pretty sure the world would be a better place.

What do you think? Any that I missed? What would you add to the list?

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