Career Crossroads: Should I Start My Own Business or Will I Be Happy Changing My Job or Career?

Ep: 9

I was looking for the next promotion, the next company to make me happy. What I realized was, if I really didn’t understand what I wanted, how could I possibly ever find it?–Blake Schofield (2:20)

Blake Schofield
Connections Illuminated

When you realize it’s time for a change in your career but can’t see the path forward, the only person who can give you the answers is you.

Your instincts are telling you that the career you’re in just isn’t a good fit anymore. The work doesn’t excite you and there seems to be no trajectory for growth. Put simply, something has to change. So what do you do?

Coming to a crossroads in your career is a very scary thing. I’ve been there. Only, instead of looking to myself for the solution, I searched around for an external answer to my problem. I thought another company, another promotion could make me happy and bring me peace. Needless to say, it didn’t work out, and eventually, I realized the fulfillment I was seeking couldn’t be found in the corporate world.

If you’re feeling unfulfilled and lacking clarity in the future of your career, you’re facing one of two choices: should you stay in the corporate arena or break away and start your own business?

If you could have anything, what would it be that you don’t have today?” – Blake Schofield. (6:03)

This is not uncommon. Many people transition from career path to career path throughout their lives. If you’re looking for the best way to make your big decision, I’d love to share some questions you can ask yourself to get clear on your path forward.


  • What makes me unhappy? It’s often much easier to figure out what we want when we begin by figuring out what we DON’T want. Usually, the things that are the most obvious are the ones that frustrate us. Maybe you’re feeling a lack of control with your schedule, or you’re feeling guilty about missing time with your family. Whatever it is, write it down. You want to aim for 10-15 items on this list. Don’t just go for the surface-level stuff. Dig deep.
  • What do I wish was different? What is it that you don’t have right now that you want? Maybe you’d only be doing parts of the job you do now, or your schedule would be more flexible. Write down 10-15 on this list as well.
  • Where can I find these things? What career would allow you to have the things you want while avoiding the things you don’t? Is there another company or job that fits your criteria? Beware, when you’re job searching, of seeking out more of the same stuff that made you unhappy to begin with. Of course, we look for similar jobs because that’s comfortable and familiar. If you realize at this point that there’s no corporate position that matches up, fear can start creeping in.
  • If I wasn’t compromising, what would I really want? Do your research. Once you know what you want and what you don’t, really take a good look at options that might work for you. Create a “Top 5” list of great opportunities and then assess whether each one would require you to give up something you don’t want to give up. Look into the company expectations, the lifestyle requirements, whether you and your family would have the time and freedom you need.
  • Do these opportunities excite me and do I believe they would fix my issue? Think long-term on this one. Consider whether you’d want to do the job for five or ten years. If you go through your list and find opportunities that don’t require you to compromise and give you excitement for the possibility, there’s your answer! If not, it’s time to consider option B: building your own opportunity.


Building a career from scratch is a scary prospect – but it’s also an amazing opportunity to learn and grow.

If none of the possibilities on your list are what you need, revisit the list of what you actually want. Think about more than the tangible aspects – the paycheck, the time off. Think about the deeper parts of your life that your current job situation is affecting. Are you less present around your family? Have you lost your sense of community with your friends due to lack of time, or are you missing out on dream trips/volunteer opportunities that have been on your bucket list forever?

Ask yourself, “If I didn’t have to worry about finances or it not working, is there anything that would hold me back from going after what I want?” If you realize that money and risk are the only obstacles to pursuing what you want to do, this route is worth considering.

Entrepreneurship is not for everyone. It requires dedication from you, a willingness to work hard, and a high level of accountability and responsibility in your business. But there is very unique freedom found in building your own business that you can get nowhere else.

There has never been someone that entered into entrepreneurship confident that they had all the answers, with no fears, and doubts, or worries.” – Blake Schofield. (13:12)

Above all, the decision you make should not be decided by your fears or doubts. When you make decisions based on your uncertainties, you end up compromising, and down the road end up right back where you started – feeling unfulfilled and looking for a way out. Whatever step you take should be taken from the pursuit of what success looks like for your life. If success for you can’t be found in the corporate world, be empowered by the opportunity to create it for yourself.

Getting out of your situation, if you don’t have a clear path to where you want to be, will likely end up creating a situation that is worse, not better, than where you are today. If you are currently trying to decide if you should start your own business, or if a change in career would be a better fit, use this free tool to gain some clarity in your own unique situation! You don’t have to settle, and you don’t have to jump from one unfulfilling situation right into another.

Rather than hoping the grass will be greener, identify what the RIGHT next step is.

We can help you do just that.

Get clarity on where you are on your journey to career fulfillment, where you’re headed, optional paths to get there, and the right next step to take.

Start your complimentary, Personalized Career Fulfillment Plan by going to

Want free resources to set your job search up for success? You can get them by going to: