Where are you at in your solopreneurship journey? Depending on which of these 6 phases you’re in, you’ll be experiencing different types of difficulties — and there will be specific steps along the way that you need to take in order to shift out of that phase and into the next one.

These are milestones that we ALL go through, by the way!

For example, here’s a timeline of (part of) my own solopreneur journey: 

(You can read the full story of the struggles I’ve faced as a solopreneur in a recent blog post I wrote)

  • November 2013 — Ideation phase (milestone #1): Realized that I was no longer willing to stay at my 9 to 5 job! I was already side hustling at the time, and I knew that I couldn’t work for anyone else any longer. I wanted to be able to have control over my own schedule, and I wanted to make my own decisions (without an employer to tell me what I could/couldn’t do). 
  • November 2013 - March 2014 — Action phase (milestone #2): At this point, I was being highly strategic in all of my actions to ensure that I was making great progress with my side hustle, outside of my 9 to 5 job. Lots of strategy planning, marketing, and freelance client work!
  • Summer 2016 - Spring 2017 — Customization phase (milestone #3): I’d learned a lot from being a freelancer for MANY years by this point, but I’d really “condensed” a lot of my learning after going full-time with my business. This was the time when I was revisiting a lot of my processes and figuring out how to do things in a way that felt fantastic for my learning style and personality.
  • September 2018 - January 2019 — Confidence-building phase (milestone #4): I was dealing with a ton of confidence issues and self-trust issues after my 1-year business partnership dissolved, so during this time, I was starting to learn how to reconnect with my own abilities and overcome all of the fear and discomfort that had flared up.
  • Spring 2019 - Autumn 2019 — Satisfaction phase (milestone #5): Now that I was back on track as a solopreneur, I was excited to have a lot more freedom in my business direction and offerings.
  • October 2019 - Present — Sustainable Scalability phase (milestone #6): This was the time when I’d already experimented a ton in my business and have been carrying out my big vision!

You’ll notice that there are gaps in the above timeline. That’s okay! Sometimes that’s because we’re sitting at a particular phase along the way contentedly, or we’re shifting in and out of a few phases at the time. 

What I want to highlight here are 5 things: 

  1. I’ve been exactly where you are now <3 I’ve struggled with many of the things that you’re currently struggling with, and I KNOW how hard it can be. I remember it vividly! This didn’t happen overnight for me. I’m not some kind of magical unicorn; I didn’t snap my fingers and suddenly have a successful solopreneur business. There has been a huge amount of trial & error, self-discovery, calculated risk-taking, strategic action-taking, missteps and mistakes, and a lot of learning along the way.
  2. It does NOT need to take 6 years in order to achieve all 6 milestones! You can achieve these milestones MUCH faster when you have a support system along the way. That’s the exact reason why I offer the Solopreneur CEO 6-month 1:1 coaching & mentorship program — we’ll address the various phases along the way so that you can go through them at a much quicker pace than I did. 
  3. Some people can get really stuck in different milestones along the way, whereas other people have no problem with that particular phase of the process. You can’t compare yourself to anyone else’s journey. It’s okay if some phases are more difficult for you than other phases! In fact, with many of my clients, we focus much more heavily on a couple or a few of these phases, rather than giving equal weight to each of the phases — because certain phases are more of a struggle vs. easier for them than others.
  4. As solopreneurs, we go through these 6 phases at varying “scales” and to varying degrees along the way. For example, you could go through all 6 phases on a much smaller scale of putting together and completing a project. You could also go through all 6 phases on the much larger scale of the full solopreneurship journey (you’ll notice that in my case, I actually started my timeline about 5 years after I’d already been a side hustler — which is because I’d been dipping in and out of various phases previous to that pivotal moment).
  5. I didn’t do my business all on my own. Even as a solopreneur, I still got help along the way! I had a couple people who I’ve considered as my mentors; I took e-courses to develop my skills; I joined coaching programs; I collaborated with business friends; I invested in business software and supplies; I took continuing education and professional development to take my skills to the next level. Let me be very clear here: You do not “need” to make the same investments as I have in my own business (and frankly, not all investments are equal! I’ve made some investments that haven’t paid off; this sometimes happens) — and at the same time, some things WILL help you significantly throughout your business journey. I designed Solopreneur CEO to provide you with the level of support that, in my experience, can be EXTREMELY helpful to your business success. (And judging by the rave reviews I’ve received from my 1:1 clients, they agree!)

Let’s explore the 6 phases & milestones every solopreneur experiences along the way throughout their journey…

Milestone #1: Ideation phase

At this point, you’re dreaming big! You’re coming up with ideas for what you want for your solopreneur business. You’re getting clarity on what it is that you do — and don’t — want. This is your vision for your life and your business, and you can start to see how they fit together and support one another.

How to know if you’re stuck in this phase: You are probably restless with your 9 to 5 job (or your current business). You know you want something different, and you’re starting to get an inkling of an idea of what that could be. You’re able to identify the things that you do NOT want for your life and business, BUT you might still be stuck on figuring out what you DO want… and you’re not sure how you’re going to get there, either.

What you need to do to move into the next phase: Get COMPLETE clarity on exactly what you want from your life and business, *and* pinpoint the BEST ways to transform your big business dreams into reality.

How we do that: In Solopreneur CEO, we use identity work and intention setting, a productivity magic audit, and comprehensive business planning for you to get true clarity in your business.

This works even for my clients who feel like they have a million different ideas spinning around in their head, and for my clients who have no idea what they want to prioritize first, and for my clients who struggle with indecision.

Milestone #2: Action phase

At this point, you’re taking action! You’re implementing what you’ve figured out that you want to do in your business, and how that can fully support your personal life goals/values and ideal lifestyle. You’re making progress on the goals you’ve set for yourself.

How to know if you’re stuck in this phase: You know what you WANT to do — but you don’t have the time or energy to take action, and you’re not sure how to change that.

What you need to do to move into the next phase: Take back control of your time and energy, and escape the cycle of burnout and overwhelm.

How we do that: In Solopreneur CEO, we use energy advancement techniques, burnout prevention planning, and goal achievement strategies for you to increase your energy (and improve your time management skills using tactics that actually work for your personality) so you’re capable of taking action in your business — without exhaustion getting in the way. 

This works even for my clients who are currently experiencing burnout, for my clients who have small kids and busy 9 to 5 jobs while growing their side hustle, and for my clients who are scaling their existing business.

Milestone #3: Customization phase

At this point, you are customizing everything in your business! You’re taking your systems, content, business structure, etc, and ensuring that you are excited about all of it. You're having fun getting creative in your business.

How to know if you’re stuck in this phase: You often copy and paste what others do, or you feel resentful that you “need” to do this vs. that in your business. There are specific tasks you really don’t like doing in your business but you don’t see any other option, and you might be struggling to be inspired.

What you need to do to move into the next phase: Start creating from a place of *making your own rules* — Doing things in your business because it’s what YOU desire, rather than “going through the motions” and copy/pasting what you see others doing in your industry. Bring back the spark to your creativity!

How we do that: In Solopreneur CEO, we use creative consciousness and ideal business development to tap into what you genuinely want in your business, so that you are inspired and creating the best (customized) structures and content for your unique situation.

This works even for my clients who feel uncomfortable stepping outside the box, for my clients who have struggled with consistency in the past, and for my clients who are afraid of the uncertainty that comes with changing their approach.

Milestone #4: Confidence-building phase

At this point, you stop letting fear hold you back! You embody your most confident self (you will be delightfully surprised at how confident you can be!) and you are able to keep making awesome moves with your business so that you accomplish your big goals. 6 Milestones of Solopreneurship: how to become your own Solopreneur Success Story

How to know if you’re stuck in this phase: You’ve started to improve your confidence in some areas of your business, and you logically know you’re highly capable as a business owner… but emotionally knowing that is a little different! You might have difficulty with your mind/body connection, and a lot of discomfort might be casting self-doubt and insecurities.

What you need to do to move into the next phase: Shift your response to fear, reframe your approach to the scary and uncomfortable things in business, and jumpstart your confidence.

How we do that: In Solopreneur CEO, we use powerful self-coaching tools and somatic techniques, confidence booster blueprint thought exercises, dynamite rule breaking, and maverick leadership embodiment for you to truly increase your confidence.

This works even for my clients who struggle with imposter syndrome and insecurities, for my clients who don’t think they have “mindset issues,” and for my clients who are already pretty confident.

Milestone #5: Satisfaction phase

At this point, you genuinely enjoy everything about your business — including the systems, processes, and structure your business exists in (this is about pleasure not just in the projects/tasks themselves, but also in how you approach those tasks). Your business feels fun and delightful for you, and there’s a lot of spaciousness.

How to know if you’re stuck in this phase: Although you love so many things about your business, there are still some elements of your business that don’t light you up — and as a result, you tend to neglect those parts of your business. Now that you’ve started enjoying your business a lot more, the parts of your business that you don’t enjoy just seem that much worse in comparison! They're dragging you down.

What you need to do to move into the next phase: Assess every aspect of your business and ensure that you sincerely delight in all of it... and be willing to "shake things up" if something is no longer working for you.

How we do that: In Solopreneur CEO, we use sophisticated simplicity methods, ease analysis, and the business structure blueprint for you to dramatically enjoy your business much more — plus thought exercises and high-level coaching to help you move past your frustrations.

This works even for my clients who are prone to over-complication, for my clients who have aspects of their business that bore them to tears, and for my clients who don’t believe there’s any way they will be able to enjoy an irritating part of their work.

Milestone #6: Sustainable scalability phase

At this point, you finally feel like a real CEO, your business is able to run itself without you needing to be at the helm 24/7, and you have the courage to continue to pursue your dreams... Your business has the capacity to grow with ease, while supporting both your clients/customers AND yourself.

How to know if you’re stuck in this phase: You feel restless in your business (and some aspects of it might no longer be challenging enough for you)... Even though your business has grown and you’ve increased your time and energy, you have a habit of immediately filling up that space with more, more, more, so it feels like you’re getting in the way of your own business growth.

What you need to do to move into the next phase: Develop your self-honesty and self-trust, and fine-tune your business as needed as a result.

How we do that: In Solopreneur CEO, we use transformational professional excellence, deep inner mindset work, self-trust and self-honesty development, and daring business growth for you to increase your courage.

This works even for my clients who don’t necessarily want to scale their business, for my clients who constantly need something else to challenge them, and for my clients who are already highly self-aware.


There you have it! The 6 “solopreneur success” phases and milestones.

So, I’m curious…

Which phase are YOU in right now?

Share this blog post on social media along with which phase you’re currently experiencing — and be sure to tag me, @Saganlives on Twitter and Instagram, so I can see your answer!

Join Solopreneur CEO to move faster, more easily, and more enjoyably through each of the 6 phases:

Hey there! I'm Sagan, your anti-hustle Productivity Strategist & internationally board-certified Success Coach.

I teach solopreneurs, multipassionates, and small business owners—just like you—how to save 10+ hours/week, EVERY week, WITHOUT burnout or overwhelm... so that you can finally achieve your audacious business goals & your dreamy lifestyle.

Ready to get started? Join Solopreneur CEO now.