Running an online business involves SO much. A lot of it can feel overwhelming because we’re trying to implement too many things at once. People ask me how I can do EVERYTHING I do because they’ve only seen the middle part of my growth. I didn’t start out where I am. Remember, EVERYONE starts from zero. Asking me how I do everything (when you’re just starting out) is like a couch potato wondering how to run a marathon before they’ve never even jogged a lap.

My business (coaching and selling informational content) now involves:

  • Writing blog posts
  • Making PDF workbooks
  • Creating promotional graphics for my blog
  • Creating promotional graphics for my products & services
  • Scheduling social media posts
  • Writing sales emails
  • Writing nurture emails
  • Hosting webinars
  • Weekly team meetings
  • Income generation planning
  • Content planning
  • Keeping my sanity
  • And so much more!

But guess where I started? By writing a simple blog post. I started out writing about style, but then realized I wasn’t passionate about it at all. So I started writing about personal development–a topic I still really enjoy. Then I started talking about my growth as an entrepreneur (when I was still running my online creative agency). Ding, ding! I found my sweet spot. People wanted to know about my journey as an entrepreneur and how to run an online business effectively. So I wrote about that.

When I started my blogging journey, I focused on creating blog graphics, creating a free PDF (sometimes) and writing the actual post. Then I would share it on my Facebook and Twitter. I did it all a couple times a week. At the time, it was in addition to running my creative agency, so it wasn’t my primary source of income. In fact, I wasn’t getting any income from blogging at all. I was simply creating content that helped me build my expertise as an online business owner.

I didn’t know what I was doing, and I certainly didn’t think anyone was paying attention. One day someone in my hip hop dance class came up to me and said “hey, I read your blog and I haven’t seen a new post this week.” That was the accountability comment I needed. If ONE person was watching, that was enough for me to step my game up. I started blogging THREE times a week for 3 weeks and my numbers shot up. From there I started scheduling my posts with CoSchedule. I also added in a “coaching” tab to my website where I was coaching for $50 – $125 per session.

I created content. I showcased my expertise. People trusted me. People hired me. It was my first taste of creating income that wasn’t from web or graphic design. Fast forward a year and a half, and I’m making a full-time income from creating information products (courses, classes, eBooks, etc). But it all started because I took the time to write ONE blog post. I did it consistently and got better.

It took me about 12 months of creating content to become an “overnight success” as a blogger.

Not many people saw my beginning because in the beginning there aren’t as many eyes on you. Most people just see the long list of what I do now and think that it all happens at once. Which is just not true. I’ve gone through different seasons and documented different processes to get where I am.

I started out in 2008 as a computer nerd who enjoyed fooling around with graphics online. When someone offered me money for it, I decided I wanted to take it seriously and began seeking clients. As I got better, I specified my niche and started making more money. I then transitioned into doing it full-time by dropping out of college in 2013. It was scary, but necessary. After designing full-time and making the most money I had ever made, I started incorporating blogging, coaching, and passive income via informational products in 2014. I eventually decided to start teaching online full-time in 2015. That was also scary, but again, it was necessary. I entered a new season because of it. One where I generated the most money I’ve made yet (I’m talking $10,000 – $16,000 in ONE month consistently for over 5 months).

If you’re noticing a trend here, you’re right on cue. Every time I shifted seasons, I made more money and experienced more joy and freedom.

Late 2015 was a good season for me.  I had just transitioned from closing down my creative agency. And my business had a growth spurt and my brand was becoming more clear to the world. Now I’m shifting into a new season of building my offline presence.

Shifting from season to season requires OBEDIENCE and a deep belief in your purpose. I’ll dig deeper into that in another blog post, but understand that season shifts are not easy. They’re not meant to be easy, but they are worth it. In fact, you’ll realize that the hardest decisions you make are often synonymous with the best decisions you make.

Regardless of which season of your business you’re in, you have to appreciate growth and understand that even with all the work you put in, there’s a process that has to be respected. You can’t run a marathon before you’ve learned to jog a mile. Likewise, you can’t expect to bring in six figures before you’ve learned to attract an audience.

This blog post is about understanding the different seasons of being an entrepreneur and how to effectively navigate the transitions to alleviate overwhelm. Each season requires different, specific goals and tasks. We become overwhelmed when we work on things we have no business focusing on.

What to do for each season


Always start with a clear understanding of where you currently are. What is your current reality vs. where you want to be? Be honest with yourself: “The reality is, I’ve accomplished _______, but I deserve ________.” Then, Identify and eliminate distractions, write down everything you think needs to be done, narrow down very specific goals, and then, think ahead to where you want to be in your next season.

1. Identify & Eliminate distractions

Distractions involve anything that’s “nice to have,” but not necessary. It’s anything that won’t make or break your business. It’s necessary to have a website and social media for running an online business, but it’s not necessary to be on 20 social media platforms at once. Distractions happen when we don’t FOCUS. Eliminate distractions by making decisions and having a clear focus.

2. Write and choose your goals

You can do everything, but you can’t do everything all at once. At this point, it’s a good idea to brain dump. What are the most IMMEDIATE things you want to accomplish. Tip: Everything can’t be immediate. Identify the purpose of the season you’re in, then create a task list that aligns with your season. Chose 2 – 3 tasks at a time and give yourself a deadline! Once you’ve met your goals and deadline, decide what the next immediate actions are. Be sure to celebrate yourself even when you achieve even “small” wins.  This helps to build your confidence, which is necessary to keep going.

Let’s say your goal for your new season is to create a foundation for people to get to know you online. Some examples of bite-sized tasks would be:

  • Create and design my free PDF lead magnet
  • Put up my coming soon page with a linked freebie
  • Get 100 newsletter subscribers by promoting my freebie

These are specific and manageable goals that you can break down into two-week deadlines. Then, identify what else is on your list that you can accomplish within 14 – 21 days. Most people just create a long to do list and feel like there’s no end.

3. Consider what the next season requires

After you’ve gotten a handle on the tasks and met the major goals from your current season, it’s time to consider what’s next for your business. Keep in mind that a season can last from 60 days to 5 months, and that its length depends on your growth, which comes from the amount of time and/or money you’ve been able to invest.

It’s important not get too comfortable within a season, but to recognize when it’s time to move forward. When we stay in one season too long, bad things can happen, which I’ll explain later. It’s time to move forward once you’ve created a systematic routine that produces consistent results.

Season transitions should be both exciting and scary. It’s not supposed to feel comfortable. So, if you’re feeling scared and nervous, remember that it’s normal. You will have uncertainty, but you should feel like you’ll make it out alive. Seasons will seem shorter each time you experience them because you’ll be a more seasoned business owner each time you transition. Each time will feel slightly less intimidating because you’ll already know what failures can arise.


1. The Dream Season

This is the stage where EVERYONE starts. Even if you have a great deal of experience in business, when you start something new, you’ll always start as a dreamer. This season involves a lot of ideation. Everyone starts here, but not everyone moves past it. Anyone can come up with an idea, but not everyone is willing to put in action.

The pros and cons of the dreamer are:


  • Seemingly great ideas
  • Lots of creativity
  • Prioritized a lot of time (because they don’t have the money)
  • Extremely passionate

Cons ((When you stay in this season too long))

  • No money coming in
  • They spend time on the wrong things
  • Too many “yes” men
  • False confidence in the wrong things
  • Worry and doubt kicks in
  • Unrealistic measures
  • Lack of clarity
  • No action
  • Passion isn’t enough

The person in this stage goes through a lot of back and forth in their head. They have confidence from family and friends (and “yes” men), but they don’t have confirmation from an actual audience. They spend too much time on the wrong things like visual branding, starting social media accounts, and getting their website out. But they should be spending time researching the market, and making the right time and money investments. They don’t understand that a website and business is never perfect. They lose sight of “done is better than perfect” and try to tweak so much that they never get their idea out in the world. It’s easy to over fantasize and not make your dream a reality.

When you stay in this season too long:

Nothing gets accomplished. You remain a dreamer not a doer. You overplan which means you’re not executing and implementing. You consume too much content without producing any results. So then, worry and doubt begin to kick in because you haven’t allowed yourself to succeed. Again, small wins allow you to celebrate yourself and build confidence.

How to transition:

Understand that done is better than perfect. Trends are always changing, so you will have to grow with the business. You can’t “set it and forget it” when it comes to your promotional and marketing efforts. You should focus on starting with the basic, necessary tools and education that will help you get to the next level.

2. The Do Season

This season is all about focus. People in this season have some money coming in, and they are busting their butt. The doer does EVERYTHING in their business. They are in charge of blog posts, emails, marketing, social media, obtaining new clients, updating their own website, etc. They are in the creative stage where staying up until 2 in the morning is the new normal. Waking up at 5 a.m. to finish a quick project? No biggie. Coffee and adrenaline keep you going…at least temporarily. At this stage, doers invest all their time and money, but don’t know how to scale.

You can plateau in this season. So now you have to start thinking about creating processes and systems, as well as build a team that will help you scale. You have to be willing to turn down “opportunities” for money. This means pushing aside instant gratification for long term growth. It’s like my mom used to say, “don’t have the penny so close to your eye that you can’t see the dollar a few feet away.”

The pros and cons of the doer are:


  • Not afraid of hard work
  • Knows how to run everything in the business
  • Actually making money


  • Overwhelmed with too much hard work
  • Not sure how to implement SMART work
  • No systems or processes in place
  • Going months with 4 – 5 hours of sleep becomes unrealistic

When you stay in this season too long:

In this season, it’s easy to start neglecting purpose and focusing too much on profit. Money is coming in consistently, but you’re still overwhelmed. You lack the urge to build systems and processes because you do everything yourself. You’re not hiring the right contractors and interns. You become a control freak with a “who can do it better than me” mindset.

How to transition:

You need to hire people that are smarter than you. Pay close attention to your daily tasks and document them. Delegate things that technology or anyone else could do. Focus on what YOU do best. Hint: Scheduling out your social media is not what you were born to do long term. Create standard operating procedures for your business. This sounds more fancy than it really is. Simply stated, you need to create a system that makes every employee/intern/contractor IRREPLACEABLE. If you can create a system, it becomes easier to relinquish control. If your biggest fear is someone not doing the job right, then hire someone that can implement a foolproof system.

3. The Drive Season

In this season the money is still great. Profit might dip because you’re investing in tools and people for automation. Congratulations, you’re a real business owner! Hope you have your LLC and bank account set up!

You’ve gotten your time and freedom back. You’re feeling satisfied. Like a boss, if you will. You have systems that are put portions of your business in cruise control. In this stage, it’s easy to get comfortable, so be careful. It’s important keep adding new ideas to the business (dipping back into the dreaming and doing phases). You just have to judge when it’s the right time to develop new ideas or when you should be building on existing products.

It also becomes easy to start working on money-making products that are misaligned with your value. Remember: just because you CAN do it, doesn’t mean you should. Learn to control the “dreamer” in you that wants to implement every new idea that comes to your head.

Here are the pros and cons of the driver:


  • More freedom
  • Some systems in place
  • Trustworthy team
  • Consistent income
  • Feeling like a boss


  • You start creating products just for money (misaligned with your brand purpose)
  • You forget to promote your existing products, services and content
  • You get too comfortable
  • Your profits start to dip

When you stay in this season too long:

You start working on money making products that are misaligned with your brand.

How to transition:

Get your head out of your ass! You have WAY more people to reach. Start consuming content by experts who are better than you. Identify areas where you can make your business better and scale more without compromising your values.

4. The Dictate Season

Dictators are oppressors. Being a leader is better, but I needed to use “dictate” for the sake of alliteration. Plus, if you don’t learn to be a strong leader, you very well could become a dictator or someone that gets walked all over. Very few businesses make it to this stage. There’s A LOT of money at this stage. I’m talking a million dollars, MINIMUM.

In this season, you have to be intentional about being a good leader, about your mindset, and about working on your personal development.

Here you can either start something new or go back to refine your existing content, projects, systems, and/or parts of your business.

The pros and cons of the dictator/leader:


  • A lot of opportune time
  • People will seek you for opportunities instead of the other way around
  • You’re a millionaire


  • You have way more to lose

When you stay in this phase too long:

You start to get so comfortable with your working systems that you ignore market shifts. You don’t take the time to ideate the use of new technology. Remember Blockbuster? The company that used to sell VHS and eventually started selling DVDs. Yeah, them. They failed to adapt to the next big change (live streaming video) quickly enough and Netflix took over.

How to stay on top:

Be open minded. Learn to adapt, quickly. There’s always someone coming after your spot. Trends are changing VERY quickly, and if you don’t stay updated, you’ll become outdated. Don’t allow your ego to get you left behind.

I’m currently in the drive season. I spend less time making more money, and I grew comfortable with my free time. I’m working on refining my systems for my online presence and dipping back into the do season to learn how to grow my offline presence. Everyday is a learning process.

What season are you in? What’s been the hardest part about transitioning? Feeling stuck or like you’re ready to transition. Download the Seasoned Entrepreneur’s Guide To Next Level Transitions!

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