Expectations vs Reality When Starting Your Own Lifestyle Business

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Expectations vs reality is a pivotal theme to consider as you embark on the journey of establishing your own lifestyle business.

The idea of shaping your own schedule and having the freedom to operate from any corner of the globe is undeniably attractive. However, it’s crucial to have a clear understanding of what this path actually demands.

I’ve spent over 13 years running online businesses and have had the incredible opportunity to travel through more than 35 countries during this time.

When I launched my first online venture in 2010, equipped with just a laptop and a drive to escape the conventional work environment, my mind was brimming with aspirations. Over the years, my endeavors have diversified to include online courses, affiliate marketing, software, coaching, e-commerce, email marketing, and more recently, blogging.

This journey, though laden with enriching experiences, hasn’t been a walk in the park.

The freedom to explore different cultures and places has been amazing, but it’s had its share of challenges along the way. Long hours, financial uncertainties, and the constant need to adapt to new scenarios, to name a few.

In this post, we’ll explore the expectations vs realities of starting a lifestyle business.

You’ll uncover insights, strategies, and tools that can support you in building a strong foundation for your enterprise.

We’ll also delve into how you can shape a journey that is both rewarding and sustainable, while remaining optimistic but also realistic.

What is a Lifestyle Business?

A lifestyle business is essentially one that is geared towards supporting the kind of life you want to live.

It’s not just about financial gain but also about fulfillment and freedom. These businesses are often online-based, which gives the owner the flexibility to operate from anywhere with an internet connection.

This could be anything – a blog, an e-commerce business, online courses, or freelance services. The fundamental aspect is that it allows you to create a balance between work and your personal life, which could include travel, hobbies, or spending time with family.

YLB 90 Day Goal Setting Planner

Your Lifestyle Business 90 Day Goal Setting Planner


Unlock Your Potential with the 90-Day Goal Planner Journal

Transform your life and achieve your dreams with our 90-Day Goal Planner Journal, the ultimate tool for setting and tracking your personal and professional goals.

With the YLB 90 Day Goal Planner Journal, you can:

  • Plan & track your goals & dreams through a comprehensive 90-day framework
  • Align your personal and business goals with your core values, ensuring a balanced and fulfilling journey
  • Break through limiting beliefs and unlock your full potential by addressing the obstacles that hold you back
  • Benefit from regular reflection and adjustment, enabling continuous growth and improvement in your entrepreneurial pursuits
  • Strengthen your commitment and accountability by tracking your progress and celebrating your achievements along the way
  • Dare yourself to dream bigger and reach new heights in your personal and professional life

Grab the planner now and get $100 OFF my brand new video course 'The Solopreneur Success Formula' plus free downloadable printables, partner offers and lots more!

Why Run a Business From Anywhere?

The idea of running a business from anywhere in the world is incredibly appealing for several reasons.

First and foremost, there is the freedom it provides. You are not chained to a desk or bound by a typical work schedule. This freedom can lead to a higher quality of life and more personal satisfaction.

Additionally, it opens the doors to endless learning opportunities. As someone who has traversed through the bustling markets of Dubai, tasted the intricate flavors of Thai street food, and hiked the breathtaking trails of Yosemite, I can attest to the personal growth and inspiration that travel brings.

These experiences can, in turn, fuel creativity and passion for your business.

Moreover, operating a business online often means lower overhead costs compared to a traditional brick-and-mortar establishment. This can translate to a leaner business model and potentially higher profit margins.

However, before you pack your bags and book a one-way ticket to Bali, it’s important to have a clear understanding of what to expect.

The difference between expectations vs reality can be vast, and this is precisely what I aim to bridge in this article. So, let’s dive in!

Expectations vs Reality – The Allure of the Lifestyle Business

expectations vs reality

Expectations: Complete Freedom and Flexibility

Control Over Schedule

One of the most enticing prospects of a lifestyle business is the perceived ability to have complete control over your schedule.

The idea is that, as your own boss, you can set your own working hours. No more waking up to the dreaded alarm at 6 a.m., no more rush-hour traffic, and no need to ask permission for a day off.

In theory, this level of autonomy can result in a more relaxed, efficient, and personalized work routine that adapts to your lifestyle.

Choice of Location

Additionally, the digital nature of lifestyle businesses usually means you are not tied to a particular geographic location. This gives you the freedom to work from anywhere, be it a quaint coffee shop in your hometown or a sun-soaked beach in Bali.

The excitement of being able to explore new destinations while maintaining a steady income is, without doubt, a dream for many.

Reality: Hard Work and Dedication

Behind the Scenes – What It Really Takes

As someone who’s been through the grind, I can assure you that the road to building a successful lifestyle business is paved with hard work and dedication.

The glamorous images of working on a laptop by the beach are just the tip of the iceberg. Behind the scenes, there’s a tremendous amount of effort involved, from managing day-to-day operations and troubleshooting technical issues to customer service and marketing.

It’s not just about setting up the business; it’s about continuously striving to improve and grow it.

Balancing Work, Travel, and Personal Life

One of the biggest challenges of running a lifestyle business, especially when you’re globetrotting, is finding the right balance between work, travel, and personal life.

Time zone differences, unpredictable travel schedules, and the sheer allure of new destinations can easily throw you off your work routine.

This requires meticulous planning, self-discipline, and the ability to set clear boundaries to ensure that your business doesn’t suffer while you’re quenching your wanderlust.

Expectations: Easy Money and Passive Income

The Notion of “Making Money While You Sleep”

The phrase “making money while you sleep” has been popularized by countless internet gurus and is often associated with lifestyle businesses.

Many people believe that once their online business is set up, it will generate passive income with little to no effort. This prospect of financial freedom without the shackles of a 9-to-5 job is undeniably alluring.

Minimal Time Investment

Alongside passive income, there’s notion of expectation vs reality that a lifestyle business requires minimal time investment. The belief is that, once the initial setup is complete, the business will practically run itself.

This ostensibly frees up vast amounts of time to pursue personal interests or simply enjoy the fruits of your labor.

Reality: Financial Uncertainty and Risks

Variable Income Streams

A lifestyle business, especially in its early stages, may not have a steady stream of income.

Unlike a salaried job, your earnings can be unpredictable. Some months you might be riding high, while others could be lean.

This variable income necessitates prudent financial management to ensure sustainability during slower periods.

Investments and Expenses

Setting up and growing an online business also involves various investments and expenses.

Whether it’s paying for web hosting, marketing campaigns, or business tools, these costs can add up. Additionally, as a digital nomad, you’ll have travel-related expenses to consider.

It’s crucial to have a financial plan that accounts for both business and personal expenditures.

Expectations: Living the Dream Life Instantly

Traveling and Experiencing New Cultures

Combining business with the pleasure of travel is a cornerstone of the lifestyle business model.

For travel enthusiasts, the ability to travel the world, immerse oneself in different cultures, and meet people from various walks of life, all while maintaining a business, seems like the perfect life.

Pursuing Personal Hobbies and Interests

With the anticipated freedom and flexibility, many believe that they will have ample time to pursue hobbies and personal interests.

Whether it’s learning a new language, delving into the world of photography, or honing culinary skills, the lifestyle business model is seen as the gateway to personal development and fulfillment.

Now, while these expectations paint a tantalizing picture, it is essential to juxtapose them against the practical realities that accompany the journey of building and sustaining a lifestyle business.

This reality check will not only ground your aspirations but also equip you with a more informed perspective as you embark on this exciting venture.

Reality: Steep Learning Curve

Acquiring New Skills

Running a lifestyle business is not just about executing a great idea; it’s about wearing multiple hats. You’ll need to be part-entrepreneur, part-marketer, part-customer service rep, and much more.

This demands the constant acquisition of new skills. From understanding SEO to mastering social media marketing strategies, you’ll find yourself in an ongoing learning process.

Continual Adaptation to Markets and Technologies

The digital world is ever-evolving, and staying abreast of changes is essential. Whether it’s new technologies, market trends, or changes in consumer behavior, your ability to adapt will be continually tested.

For instance, AI is about to irrevocably change the world as I write this. Adaptability is not just an asset; it’s a necessity in the realm of all businesses.

In conclusion, running a lifestyle business can be an enriching and rewarding endeavor, but it’s not without its challenges.

Setting expectations vs reality apart and being prepared to put in the work are critical factors in determining your success in this adventure.

Expectations vs Reality – Setting the Right Foundations

Here are some foundational principles to help you grow your lifestyle business in such a way that traveling the world, working from a beach, and having more time to pursue hobbies and interests become a reality.

Importance of Industry Knowledge

Having the right knowledge is the bedrock on which you can build a successful lifestyle business. Understanding your industry, the competition, and customer demands is critical.

For instance, if you’re looking to start an e-commerce store selling travel gear, knowing the types of products that are in demand, pricing strategies, and the various marketing channels available is essential.

What are the five most important skills you need to learn to grow your business?

Make a list and immerse yourself, one by one, in gaining those skills. This will undoubtedly give you a competitive edge.

Standing on the Shoulders of Giants

An invaluable resource that you have as an entrepreneur is learning from other people’s experiences and case studies.

YouTube videos, blogs, and podcasts abound, filled to the brim with entrepreneurs sharing their starter stories, their lessons, their mistakes, and what they’d do if they were starting over.

A physical mentor is no longer required when all the information you need to both start and grow your lifestyle business is at your fingertips.

Budgeting and Saving

Financial planning is the cornerstone of establishing a stable lifestyle business. Crafting a budget helps you keep track of your expenses and ensure that you’re not overspending.

It’s especially important to have a buffer for lean months

From my experience, I’ve found that having at least 6-12 months of living expenses saved up at any one time provides me with the financial cushion needed to focus on growing my business without the constant stress of making ends meet.

Diversifying Income Streams

Another vital aspect of financial planning is diversifying your income streams. Relying on a single source of income can be risky.

During my entrepreneurial journey, I started with online courses, added software, branched out into affiliate marketing, dipped my toe in coaching (not for me), and eventually grew a large e-commerce business.

This not only allowed me to create multiple revenue streams but also mitigated the risk associated with depending on a single business model.

Creating Support Systems

Embarking on the lifestyle business journey can sometimes be a lonely road, especially if you’re traveling and constantly on the move.

Building a network and creating support systems are indispensable. Engaging with like-minded individuals or joining entrepreneur groups and communities can offer valuable insights, moral support, and sometimes much-needed reality checks.

If you’re not sure where to start, just look for groups specific to your niche on Facebook, or come and join the Your Lifestyle Business community and network with people on a similar journey to you.

Collaborations and Partnerships

Networking can also open doors to collaborations and partnerships.

Over the years, I’ve collaborated on a number of projects with people I’ve met online, and more recently, I’ve started talks with a chap I met at an SEO conference about the potential of a future podcast together.

By chatting and connecting with like minded people, all sorts of doors could open and opportunities would appear, plus it makes building your lifestyle business so much more fun!

Having the right foundation—in terms of knowledge, financial stability, and a robust network—is essential for anyone seeking to build a sustainable and successful lifestyle business.

These elements serve as the pillars that will support and drive your business forward, even through rough tides.

Expectations vs Reality – Strategies for Long-Term Success

strategies to success

Creating a Balance

Setting Realistic Goals

One of the keys to long-term success is setting realistic and achievable goals.

It’s easy to get carried away with grand visions, but breaking them down into smaller, more manageable objectives is essential.

This allows you to focus on immediate tasks while keeping your eyes on the bigger picture. For instance, instead of aiming to visit 10 countries in the first year, focus on building a steady income stream and maybe aim for 3-4 countries.

Gradually scale as your business stabilizes.

To help you, check out our 90-Day Goal Planning Journal. Tailored specifically for lifestyle business entrepreneurs, the journal guides you through the goal setting process using our proprietary TAG (Triple Action Goals) System to help you gain momentum.

With weekly and daily trackers, you’ll find it easy to set, monitor, and fine tune your goals, plus reflect on triumphs and strategize for improvements. Use this planner to hold yourself accountable to your goals every 90 days.

Managing Time Efficiently

Time management is vital, especially when juggling work, travel, and personal life.

It’s essential to prioritize tasks and allocate time effectively.

Implementing productivity tools and techniques, such as the Pomodoro Technique, can be beneficial. When I was starting, I used to allocate specific days for travel, exploration, and cultural experiences, while other days were strictly for business-related tasks.

Finding a routine that suits your lifestyle and sticking to it is imperative.

Persistence and Adaptability

Dealing with Challenges and Setbacks

In the course of your journey, you will inevitably face challenges and setbacks. It’s part of the entrepreneurial experience.

What separates successful entrepreneurs from the rest is their ability to persist through these trials.

Take each setback as a learning opportunity. I’ve had more failures than I’d like to remember over my journey, and some have been bitter pills to swallow.

However, analyzing has helped me grow as a person and ensure I don’t make the same mistakes moving forward.

Being Open to Change and Innovation

In an ever-evolving digital landscape, adaptability is key. Markets change, consumer preferences shift, and new technologies emerge.

Being open to innovation and ready to pivot when necessary is essential. During my journey, I’ve had to adapt my product offerings, marketing strategies, and even my target audience to keep pace with the changing dynamics.

Building a Brand

Creating a Unique Identity

Your brand is what sets you apart from the competition. It’s not just about logos and taglines; it’s about the values and stories that your business embodies.

My brand, for example, has evolved to focus on building a business from anywhere in the world.

What started as pure business advice is now about freedom, travel, and exploring the world, plus I very much target the solo business owner as opposed to startups or VC funded ventures.

Your brand will evolve with you as you grow and learn new things, so start with your target market in mind and be open to innovation and change as your business matures.

Connecting with the Target Audience

Building a brand is not just about creating an identity; it’s also about connecting with your audience on a deeper level.

Engage with them through social media, share your stories, and listen to theirs. Create content that adds value to their lives.

My blog, for instance, has become a hub where I share not just tips on running a lifestyle business but also travel experiences and empowerment principles. Over time, this will foster a sense of community.

The road to building a successful lifestyle business is fraught with challenges, but with the right strategies, persistence, and a dash of passion, it’s a journey that can be incredibly rewarding.

Remember, it’s not just about the destination; it’s about the experiences, the growth, and the fulfillment that come along the way.

The Importance of Goal Setting and Planning

Why Goal Setting and Planning are Essential

Goal setting and planning are two of the most crucial aspects of running a successful lifestyle business. Goals give you a clear sense of direction and purpose, while planning helps you allocate resources and time effectively.

Moreover, goal setting is a driving force behind motivation and focus, two key ingredients to success. When your objectives are clear, your decisions are more informed, and your actions are more purposeful.

Introducing the 90 Day Goal Setting Planner

To facilitate this, I would like to introduce our “90 Day Goal Setting Planner.” This planner is specifically designed to assist lifestyle entrepreneurs in breaking down their long-term objectives into smaller, more achievable goals over a 90-day span.

The planner includes:

  • Vision Setting: A section to articulate your long-term vision for your lifestyle business. Here, you can write down what you ultimately want to achieve.
  • 90-Day Goals Breakdown: A dedicated area for setting specific goals for the next 90 days. This helps in maintaining focus and ensuring that you are taking steps towards your larger vision.
  • Weekly Action Plans: This segment allows you to plan your week, ensuring that each day’s activities are aligned with your 90-day goals. It’s also designed to promote a balance between work, travel, and personal life.
  • Reflection and Review Pages: Periodic sections for reflection on what’s working and what isn’t. This helps in assessing progress and adjusting strategies as needed.

Leveraging the Planner for Success

Using the 90 Day Goal Setting Planner can be instrumental in keeping you organized and on track.

As an entrepreneur who has experienced the challenges of running a lifestyle business, I’ve found that breaking down my goals into 90-day increments has enabled me to stay agile and responsive to the changing dynamics of both the market and my travel lifestyle.

By integrating this planner into your daily routine, you can systematically set, track, and achieve your goals while also adapting as needed. This tool can be an invaluable asset in turning your lifestyle business dreams into reality.

YLB 90 Day Goal Setting Planner

Your Lifestyle Business 90 Day Goal Setting Planner


Unlock Your Potential with the 90-Day Goal Planner Journal

Transform your life and achieve your dreams with our 90-Day Goal Planner Journal, the ultimate tool for setting and tracking your personal and professional goals.

With the YLB 90 Day Goal Planner Journal, you can:

  • Plan & track your goals & dreams through a comprehensive 90-day framework
  • Align your personal and business goals with your core values, ensuring a balanced and fulfilling journey
  • Break through limiting beliefs and unlock your full potential by addressing the obstacles that hold you back
  • Benefit from regular reflection and adjustment, enabling continuous growth and improvement in your entrepreneurial pursuits
  • Strengthen your commitment and accountability by tracking your progress and celebrating your achievements along the way
  • Dare yourself to dream bigger and reach new heights in your personal and professional life

Grab the planner now and get $100 OFF my brand new video course 'The Solopreneur Success Formula' plus free downloadable printables, partner offers and lots more!

Expectations vs Reality – Summary

As we’ve navigated through this expectations vs reality post, it’s clear that starting a lifestyle business often comes with lofty expectations of freedom, travel, and easy income.

However, the reality is that it demands hard work, financial prudence, adaptability, and a balance between personal and professional lives.

My journey, spanning over 13 years and 35+ countries, is a testament that dreams can be achieved, but not without perseverance.

The road is not always smooth; it’s paved with challenges, setbacks, and learning curves. However, it is through embracing these challenges and remaining steadfast in our pursuit that dreams morph into reality.

For those of you teetering on the brink of taking the plunge, my parting words are – go for it, but with your eyes wide open.

Equip yourself with knowledge, build a solid foundation, and be prepared to put in the work.

The world is a treasure trove of experiences waiting to be unraveled. Let your lifestyle business be the key that unlocks the doors to a myriad of adventures.

Here’s to your journey – may it be one of growth, fulfillment, and boundless discovery.

About the author

Disclaimer: Please note this post may contain affiliate links, from which, at no additional cost to you, I may earn a small commission. Also as an Amazon Associate I earn from qualifying purchases. I only recommend products and services I’ve used or would use myself. If you choose to purchase from any of my links, thanks so much for your support! 😊