How to make the transition from self-employed to employee easier

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So you’ve been your own boss for so long already, and now you want to become an employee again?

After enjoying the freedom of setting your own schedule and being the one calling the shots, going back to the 9-to-5 and reporting to someone else can be quite a big change.

So allow me to share some tips to help you make the switch from controlling your destiny to being part of a team again as seamlessly as possible.

Reacquaint yourself with the differences between self-employment and employment
  • Less flexibility but more stability

When you are the boss of yourself, you can set your hours and take leave (almost) anytime you want. But as an employee, you now have fixed work hours and a limited number of days off. The upside is you will have a steady income and (better) job security. No need to worry too much about when the next paycheck is coming.

  • No more “multitasking”

As self-employed, you’ve probably handled everything from sales to accounts and business development. Now you can focus on specific job roles and responsibilities. This means there’s no need to run across departments in a day until your brain is fried. Let the relevant departments handle their parts.

  • Following orders

So you used to make all the decisions? Not now anymore with bosses and company policies to follow. So it’s time to make the switch from speaking to listening and meet project deadlines set by superiors. But at least you no longer need to carry all the weight and pressure on your shoulders.

Preparing for the transition
  • Do a self-assessment

Sit down and think about what skills you’ve picked up as an entrepreneur. Things like problem-solving, time management, and handling pressure are attractive to employers. Recognize your strengths and how they can benefit your new company. This will boost your confidence in interviews and help you negotiate a good salary.

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  • Emphasize relevant experience

When job-hunting, focus on how your entrepreneurial experience will make you a better employee. For example, highlight how you independently built a business from scratch, innovated new products or services, won customers, managed finances, and hustled to overcome obstacles. These stories demonstrate a growth mindset, resilience, and leadership potential—qualities any boss would value.

  • Be open to change

The hardest part may be getting used to fixed work hours, less flexibility, and having a boss (again). But go in with an open mind. View your new role as an exciting opportunity to better yourself, without the stress of being solely responsible for a business.

Adjusting to the new role
  • Follow the schedule

Gone are the days when you could start work at 12 pm if you wanted. Most companies expect you to be at your desk during fixed hours, whatever the agreement is. Make sure you’re on time and take your breaks when scheduled. If you need to come in late or leave early, inform HR in advance.

  • Work with your team

Whether it’s your cubicle neighbor or a whole department, get used to collaborating. Communicate openly, share ideas, and help each other out. Having a good rapport with coworkers will make the daily grind more enjoyable.

  • Complete assignments by deadlines

As an employee, you will be given tasks, projects, or sales targets to finish by certain dates. Don’t drag it out—your colleagues and managers are depending on you. Try your best to meet all deadlines and let someone know ASAP if there are any issues.

After so long calling the shots for yourself, you now have to listen to someone else. But if you go in with the right mindset, open to learning new things and adapting to different working styles, you should be fine. Remember, be flexible, and focus on the work and not the politics. Your experience from so many years working alone will serve you well. This job may turn out to be better than you expect if you give it a proper chance. Take a deep breath and dive right in. The water will feel warm in no time.

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