Ep. 71 Lead Gen, Branding & Navigating Busy Seasons w/ Lindsay Dollinger

Apr 21

Most business advice assumes you have time. Time to batch content, time to nurture leads, time to show up consistently across every platform, time to just sit and think. But a lot of us are running our businesses in the cracks of a life that is already completely full, and the gap between what the advice says and what is actually possible can feel pretty defeating.

That is what this conversation is really about.

I sat down with Lindsay Dollinger for a true podcast swap, meaning this is airing on both of our shows at the same time. Lindsay is a business coach, travelpreneur, full-time teacher, and host of the Passports, Profits and Pixie Dust podcast. Between my three hours of focused work a day with two kids at home and her building a business around a full-time teaching schedule, we have both had to figure out what sustainable actually looks like in practice.

We got into all of it: running a business in a busy season, how branding and lead generation actually connect, and what to do when sales feels gross.

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Running a Business When Life Is Already Full

One of the first things Lindsay and I talked about is how different our "busy" actually looks. I have two kids at home, a studio manager, and a graphic designer on my team, and on a good day I get maybe three focused hours of work in. Lindsay is a full-time teacher running her coaching and travel business in the pockets of time around it.

Neither of us has the luxury of a clean, color-coded schedule. And we both had to make peace with that.

For me, that looked like giving up on the idea that I would have tidy themed workdays (Mondays for content, Tuesdays for client work, etc.) and instead operating with loose parameters: I know podcast episodes go out Monday and Thursday so those days get an audiogram, I do one portfolio post a week, and I try to get two other pieces of content out. Beyond that, I work from where my energy is that week.

Lindsay approaches it similarly. She does a high-level annual plan, breaks it down by quarter and month, and then decides week by week what actually needs to get done. She batches content when she is in a creative flow, hands it off to her VA to schedule, and gives herself permission to let the rest go.

Both of us agreed on this: the people who succeed long-term at running their own business are not the ones who are perfectly disciplined every single day. They are the ones who know when to push and when to rest, and who have built a business they actually enjoy showing up for.

If you are juggling a business with a full-time job, kids, or both, the most important thing you can do is pace yourself. Your business will still be there tomorrow. Burnout takes a long time to come back from.

On Confidence, Discipline, and Faking It

This came up naturally in our conversation and I think it is worth addressing directly because I get asked about it a lot.

People tell me I seem confident online. Confident is genuinely not a word I would use to describe myself. What I have is discipline, and a strong enough motivation to keep showing up even when I do not want to.

There are weeks where I really do not want to post on Instagram stories or show up on video. I do it anyway, not because I am brimming with confidence, but because I know it matters for my business and my family. And here is the thing: if you make yourself do something enough times, you stop being scared of it. That is not confidence, exactly, but it looks a lot like it from the outside.

Lindsay made a great point that people often confuse discipline with motivation. Motivation is unreliable. It will not show up every day. Discipline is what fills the gap. And the flip side of discipline is knowing when you are white-knuckling your way through something that no longer fits, because that will burn you out just as fast as doing nothing.

Why Your Brand Matters for Lead Generation

One of the things I feel really strongly about and that I think gets missed in the lead gen conversation is how much your brand does (or does not) support your ability to generate leads.

Most people treat branding and lead gen as separate problems. In my experience, they are completely intertwined. You can do everything right on the lead gen side, but if someone lands on your website or your social profiles and nothing resonates, they will leave without taking action. And conversely, you can have a beautiful brand and a killer website that nobody ever sees because you have no strategy for getting people there.

I see this constantly with clients. They invest in a brand and a website and then wonder why it is not working. The missing piece is almost always that nobody is driving traffic to it. A great website cannot work for you if people are not finding it.

This is why I ask every single client: we are going to build you a really strong brand and website, now how are people going to find it? The answer to that question is your lead gen strategy.

The Four Types of Lead Generation

Lindsay has done a lot of thinking about this and actually built a quiz around it because she noticed that the same strategy does not work for everyone. You can take it at lindsaydollinger.com/quiz, but here is the breakdown she shared.

Email marketing. Building and nurturing a list of people who have opted in to hear from you. This tends to be a longer-term play but one of the most reliable when done consistently.

Social media. Showing up on the platforms where your ideal clients are spending time and giving them a reason to follow, engage, and eventually reach out.

Automation. Funnels, sequences, and systems that do the nurturing work for you once someone enters your world. Lindsay puts an asterisk on this one because it only works once you have the content and the audience to feed into it.

Live events and activation events. Free workshops, webinars, challenges, anything that gets people to show up in real time and experience what it is like to be in your world. This is Lindsay's specialty and where she sees the most conversion.

Her advice is not to do all four at once, but to pick one and go all in on it for three to six months. Tweak it, learn from it, figure out what is working, and then start layering in the others. Trying to do everything at once usually means you are not doing anything well enough to see results.

You Do Not Need 95 Pages On Your Website

A lot of Lindsay's audience are travel advisors who either do not have their own website or are relying on their host agency's site. I get this question in different forms all the time: do I really need a website, and does it have to be a big complicated thing?

The short answer is yes, you need something, and no, it does not have to be complicated.

Putting all of your eggs in the social media basket is risky. Platforms go down, accounts get locked, algorithms change. A website, even a single page, gives you a home on the internet that you own. It also starts building SEO value in a way that social media never will.

For a travel advisor, that one-page site does not need to list every single trip type in excruciating detail. It needs to tell people who you are, why they should choose you over the 85,000 other travel advisors out there, and how to reach you. People are not hiring the most technically impressive travel advisor. They are hiring the one they feel like they would get along with, who has been to the places they want to go, who seems like a real person. You can communicate all of that without a massive website.

Long term, yes, having separate pages for different trip types will help your SEO. But as a starting point, a clear, simple, personalized one-pager will do more for you than waiting until you have time to build something elaborate.

On platform: I build on Squarespace and Kajabi. For a service-based business like a travel advisor who is not selling digital products, Squarespace is almost always my recommendation. It is affordable, user-friendly, and easy for you to maintain on your own after it is built. You do not need a website manager on call to update your phone number.

Why Sales Feels Gross and What to Do About It

Both Lindsay and I admitted that this is still the mentally hardest part of business, even after years of doing it.

When it is time to actually make an ask, a lot of us hear a little voice that says this is sleazy, this is pushy, I do not want to be that person. Lindsay shared a mindset shift that I think is genuinely useful: think about a specific client whose life is different because they worked with you. What would have happened if they had never found you? If they never started their website, maybe they never found five new clients. If they never found those clients, maybe they missed out on income that would have funded something meaningful for their family. You can keep following that thread as far as you want.

The reframe is not "selling is actually fun." It is that withholding what you offer has a real cost for the people who need it. And most of us who are wringing our hands about being pushy are coming from such a place of integrity that the actual risk of being too salesy is pretty low.

My version of this is that your brand, your website, and your content should be doing most of the heavy lifting before someone ever gets on a call with you. If they are showing up already knowing who you are and what you do and what it costs, the sales conversation is not really a pitch at all. It is just a two-way conversation to see if it is a good fit, from both sides.

And sometimes it is not. I have ended calls by saying, honestly, I do not think I am the right person for this. That never feels like losing a sale. It feels like doing my job.

Pick One Thing and Do It Well

Lindsay wrapped up our conversation with advice I would echo completely: do not look at all of this and feel like you have to overhaul everything at once.

If your branding is not there yet, start there. If your brand is in good shape but your website needs work, focus on that. If your website is solid but no one is finding it, that is your lead gen problem to solve. Pick the one thing that is the biggest gap right now and put your energy into that for the next 90 days. Then add the next layer.

You built your own business so you could do things your way. That includes your marketing. If you hate email, do not do email. If Instagram feels like a chore, find another platform. There is no single right way to generate leads. The best strategy is the one you will actually stick to.

Come find me on Instagram and Threads at @spectrumco. If you are not sure where to start with your brand, I have a ChatGPT-powered brand audit that will walk you through where you are and what to focus on next. The link is always in the show notes.

And go check out Lindsay at @lindsaydollinger across all platforms, or take her lead gen quiz at lindsaydollinger.com/quiz to figure out which lead gen type is the best fit for you.