How to Successfully Step into Entrepreneurship After Mid-Career


What happens when security no longer fulfills you, and change feels overwhelming? Tamara Vučković shares her experience of building her own business path — without sudden breaks, but through gradual skill building alongside existing professional commitments and community support. Through her development in virtual assistance and the role of an online business manager, she outlines the challenges, opportunities, and the importance of education through GoThrive — as the foundation for a more successful and meaningful career.
When you know you don’t want the same thing anymore, but you don’t yet know exactly what you want
Mid-career isn’t the end — it can be a beginning. It’s the moment when we consciously decide what we want our next step to look like. For many of us, it’s a time of reassessing career, priorities, and values. And although the decision to change can feel daunting, it often leads us toward a version of ourselves where we feel fulfilled and authentic.
I found myself at that exact point. And I’m still in that phase. I work in a “secure” job; I know its processes, challenges, and opportunities. But I felt something was missing. I needed freedom. Freedom to grow, to be creative, to build in my own way. I felt a strong urge to share my knowledge and experience and to use it where it could still make a difference. And even though I had the knowledge, skills, and desire, sometimes there simply wasn’t space where it was sought or recognized.
Today I am a virtual assistant, and I am slowly moving toward the role of an online business manager.
This is the story of how I stepped into the world of entrepreneurship after mid-career and what you can take from my experience.
If you also feel at a crossroads, know that you’re not alone. You may not yet know exactly what you want, but that too is a beginning.
You don’t have to have all the answers before you start
Career change rarely happens overnight. I have been doing my job for years while simultaneously involved with various institutions. Almost 25 years of juggling multiple roles, buildings, cities — in my field, within systems, with colleagues, with clients. That’s not a small number of years.
Before that, I spent several years in different companies in the field of entrepreneurial economics — dynamic, concrete, full of challenges and opportunities. Even earlier, I went through various roles that taught me not only about the work itself but also about people.
Throughout it all, one thing never stopped: my drive to explore what else was “out there.” I followed trainings, read articles and professional books, listened to podcasts, enrolled in courses — in technical, entrepreneurial, and creative areas. The GoThrive course “Virtual Assistant — How to Become One and How to Thrive” was one of the key moments. And today I continue with further development through the GoThrive program for Online Business Managers (OBM). All of this, step by step, led me to a clearer picture of what I want.
Still, it’s important to understand that change doesn’t have to be drastic and sudden. A gradual transition can be key, and I advise you not to make abrupt decisions that could jeopardize your security. If you already have a stable job, be responsible toward your current commitments. I recommend planning your transition by developing new skills in parallel with your existing obligations. This way, you’ll be ready when the time for change comes, without putting yourself in a position of financial or personal stress.
You don’t need to change everything at once — just start with small steps. Building a new career while maintaining your current employment can allow you to test new directions without taking on too much risk. Show yourself patience and accept that transition doesn’t have to be a straight line but a gradual process in which each new insight and experience helps you build a stable and successful future.
And start with what you already know. The “perfect moment” will come, but keep in mind that planning and a careful approach can make the whole process much easier and safer.
Find support and community
One of the key things that helped me amid all my desires and ideas was the GoThrive community. When you doubt yourself, when you’re not sure how to structure a service or land your first client, having people who have walked or are walking the same path makes a huge difference. That’s why I continue learning through the GoThrive OBM education — because business development isn’t a one-time project but a process that never ends.
Your first-career knowledge, experiential roles, and today’s work aren’t lost — they give you an advantage
All my tools — organization, structure, communication, listening, understanding, support, education, knowledge of systems, laws and regulations, expertise in multiple areas, digital technology — today are the value I bring to every project. The clients I work with appreciate that I come with experience, responsibility, and a broad understanding of the business context.
If you ever thought you had to “start from scratch,” know that the truth is quite the opposite: you’re starting with knowledge and experience that are your advantage.
Prepare the mindset, not just the skills
Entrepreneurship demands courage, but also a lot of inner work. I had to learn to set boundaries, say “no” to clients who didn’t align with my values, say “no” to myself, stop before burning out, manage insecurities and (still learning!) recognize my value and charge for it without guilt.
LinkedIn — my first step toward visibility and opportunities
My visibility journey began by writing posts on LinkedIn, even though I had many fears. It was completely new for me. What if people saw me, what if they asked me questions, what if something I wrote was off, would it be awkward, what if…? But those moments of writing, the content I shared, genuine and authentic, opened doors to first contacts, opportunities, and collaborations. If you’re in a similar place, just write, share, and show up.
What if right now is your moment to take the first step?
You may feel that “it’s not the right moment,” that you have too many obligations, that you don’t know where to start. But what I’ve learned is that it won’t be easier or safer tomorrow, and you can choose to be braver today. Step by step, day by day.
Mid-career isn’t a crisis, but an opportunity
My transition, balancing current professional engagements with building my own business, isn’t easy, but it’s one of the most important decisions I’ve made for myself. I want to explore both options: building a career that matches my energy, values, and lifestyle — giving me freedom and creativity — while also providing extra value through my skills and experience.
If you’re thinking about a change — GoThrive trainings for Virtual Assistants and Online Business Managers could be your first step. Join a community that offers not only knowledge but real support at every stage of the journey.
Curious what a firsthand transition from a career to entrepreneurship looks like?
Reach out to me — I’d be happy to share more of my experience or point you toward the right resources.
Your time is just beginning.
Tamara Vučković is a virtual assistant and monday.com mid-level expert who helps small and medium-sized entrepreneurs, educators, and service providers simplify their operations and save time. By optimizing processes and working on the monday.com platform, she creates efficient systems that boost productivity and reduce operational stress. If you’re looking for a partner who understands your challenges and builds sustainable solutions alongside you, contact Tamara: tamara.vuckovic@gmail.com.
