How to change careers without starting over.

Realizing what you're doing is no longer right for you is hard.

It's hard to get excited about something if you don't like it anymore.

It's hard to think all of your skills and experience might not have any value if you do something else.

And, it’s hard to think about who is going to give you a chance to do something new at all.

That's why I think it's so much easier to change careers while staying at the company you're at.

Though, unfortunately, many people don't think they can change jobs and stay where they are because all of the career advice says you either need to just be happy you have a job or that the only way to get what you want is to quit and go somewhere else.

This advice ignores the most obvious opportunity you have.

The relationships you've built at your current job are the best leverage you have to make a change and define the career you want.

You know the nuances of the company, what they value, what their challenges are, who can help you, and where the opportunities are. And, most importantly, they know you.

Imagine having to develop new relationships and prove yourself at a new company while also taking your first steps down a new career path. There are so many things you have to do right that inevitably, something will go wrong. And that's assuming a new company is willing to take a chance and hire you for a job you don't exactly have any experience with.

Now, imagine starting a new job you're excited about with people you already have relationships with, who trust you, and are as committed to your success in a new role as you are.

It sounds too good to be true.

But, I'm going to tell you the exact conversations to have and questions to ask to make it happen.

I'm going to show you:

  1. How to have tough conversations with your boss

  2. Why you have to be honest with yourself about what you want

  3. The questions to ask as you research different career opportunities

  4. How to make sure you don't pick a job that ends up being just like your old one

  5. The three-phase approach to effortlessly transition into a new role

It's all here. But first, I'm going to quickly tell you about the first time I switched jobs before I knew how to do any of this.

Create the right opportunities for yourself.

The first time I switched jobs, I went from being a project manager to a new business manager.

As a project manager, I was managing a team producing social media content for Google. But, being new to advertising, I wanted more. I was young and ambitious, and I wanted to be on different projects all of the time. Not stuck on one project with no end in sight.

And, I thought interacting with the executives at the agency was a way to fast-track my career.

To me, joining the new business team was the way to achieve both things.

I'd get to work on the most exciting projects with the best talent at the agency as we pitched all types of clients interesting ideas and new technologies.

So, I needed to figure out how I'd get there.

But, the new business team was made up of an agency executive, a director, and an account manager. And the three of them had it covered.

From the outside, though, I could tell there was no consistent process in place as each pitch looked like it was barely being held together as it was delivered. As a project manager, I believed there was a better way if someone was able to put a little structure and consistency in place.

So I started suggesting little things I thought could help.

Things I posed as questions to see if they'd thought about doing it differently. All I wanted was to be a part of the conversation. And, by bringing these things up, I figured I was at least positioning myself as someone interested in helping out if they ever needed it.

After a while, I told my boss if there were ever an opportunity for me to lead a new business pitch, I wanted to do it.

This was all I could do unless something changed.

Then, things did when the director left for another job on the other side of the country. Now a team of two, the executive and the account manager had to keep everything together, which they managed for a while.

Then, as it happens at advertising agencies, a couple of pitches were already underway when another came in that they just couldn't say no to. But, the problem was, they didn't have anyone to run it.

This was the opportunity I'd been waiting for.

I told my boss and the new business team that I was interested in running the pitch if they'd let me. It was time to see if the goodwill I'd been building up by being interested and helpful all of those times before would be enough to get me my shot.

Thankfully, they said I could if I was sure I wanted it and was willing to do it on top of my current responsibilities as a project manager.

Of course, I wanted to, and no problem. I'd make it work.

It took about a year to go from talking about wanting to work on new business to my first real opportunity. But because I was patient, helpful, and clear about what I wanted, I had positioned myself to be the person they thought could do it when they needed someone to step in.

If I'd never said anything about wanting to do that type of work, no one would have known that's what I wanted or been comfortable with me taking it on when there was an opportunity.

Luckily the pitch went well, and from there, I kept getting opportunities to lead pitches until it became inevitable that I would switch teams and work on producing new business full time.

Being capable and persistent were the keys to making it happen this first time.

The next time I switched careers, though, was a bit more formal.

I don’t want to leave, but I don’t want to do this.

Switching into new business at my first agency was great, but I started to get restless again about a year and a half later. And this time, I felt like there was no more opportunity at the company for me. So, I quit. Then the next place was fine for a while and when I felt like there wasn't any opportunity there, I quit again. And, I quit the company after that too.

I was chasing a career, thinking I wasn't satisfied with what I was doing because of the company.

That's until I got to where I am now. This time I realized it was me that needed to change.

I loved the company, but I didn't love the job. I was simply over it.

I realized the reasons I wanted to pursue a career as a project and new business manager were no longer true.

I was ready to do something else. I wanted a new challenge. And, I didn't want to shift my focus like I did the first time. This time I wanted to do something completely different—a new career in a new discipline.

I wasn't exactly sure how I would do it, but having the experience of switching careers once before let me know it was possible. I also learned from the times I'd quit and seeing the people visibly so surprised to find out that I was unhappy that I should start the conversation with my boss.

Unfortunately, most people don't do this because they're afraid of getting fired.

They think if they tell their boss they don't like their job, they'll find someone to replace them.

Naturally, the first assumption in all of this is that you have a good relationship with your boss. That's a given. But it can still be intimidating to bring something like this up, especially when you don't intend to leave. So you need to be prepared. You don't want to start a conversation about how you want to do something else but then not be able to answer any of the questions that will inevitably be asked or not propose any clear next steps.

So, if you’re like me and want to do something else but don’t want to leave the company you’re at, here are the five steps to making that happen.

Mitigate the risk of not being taken seriously by thinking through potential objections and coming prepared with a proposed plan of action.

Mitigate the risk of not being taken seriously by thinking through potential objections and coming prepared with a proposed plan of action.

1. How to have tough conversations with your boss.

It's a myth that your boss only wants to hear good news.

I used to think this way. I thought if we only talked about things that were going well and avoided anything that wasn't perfect, they would be happy. I didn't want to bring up how I was feeling or if I was struggling with something because I didn't want to be a burden or create more work for anyone. I thought if I brought those things up, people would think I was being difficult, which is the last thing I wanted people to think.

But what I know now that I didn't know then is that it's a boss's job to help the people who work for them, especially when it comes to knowing whether the people on their team are happy or not.

Bosses want people who are engaged and excited about the work.

That's why I knew that instead of silently resenting my job until another opportunity came up as I had before, the right thing was to talk to my boss first.

So, during one of our weekly 1:1's, I told her how I was feeling disengaged and uninspired by the work I was doing and that I wanted help figuring out what we could do to make it better.

We'd had a couple of conversations before this where she'd given me some feedback saying that other team members said I didn't seem to care as much as I once did. So, me bringing it up wasn't something completely new. And it was important that I was coming and asking for help instead of deflecting and not taking any responsibility for what I was doing and how I was feeling.

It was in this conversation that I brought up the idea that I might want to do something else.

I told her how the reasons I started down this career path five years before didn't seem to be the ones that would keep me in it for the long term. That when I looked at the natural progression of where this career would take me, I didn't feel like it was getting me closer to the goals I have for myself.

I told her I felt I was ready for a new challenge and wanted to learn a new skill set and wondered if that was something we could explore together.

Your boss wants to know how you feel, even when you're not feeling great.

It was important we'd had a few related conversations about how I was doing at work before I brought up the idea of switching careers, so I didn't catch her completely off guard.

Seeding the conversation like this helped make it seem like a natural route we could go down. This isn't to say it wasn't a bit shocking for her to hear one of the people on her team no longer wanted to work for her. I'm sure it was. But, she took it in stride and quickly shifted from a superior to a collaborator in helping me figure out what we should do next to see if this was even possible.

Since this was the first time we talked about me switching careers, we both agreed the next step was for me to really think about how I was feeling, what wasn't working, and what I thought I might want to do. Then we'd meet again to go over this self-evaluation and figure out what we should do after that.

Thinking back on this conversation, I think these three things made it successful and are things you should consider as you plan out how you'll bring up the idea of switching jobs with your boss.

Take the lead.

Come prepared and be ready to talk through what you're thinking so your boss has something to react to. You don't want to bring this up and make them feel like it's their job to figure it out for you. It's not. But also, don't make it seem like you already have a complete plan in mind. Doing this shows you're serious but also keeps things informal at the same time.

Ask for help.

Ask your boss for their help in figuring out your next move. This helps them feel invested and makes it something you do together. And, you're definitely going to need their help with getting everyone else who needs to sign off on this onboard.

No ultimatums.

You absolutely cannot use this as a bargaining chip. This is not about getting an offer and using it to go somewhere else or increasing your salary where you're at. The reason you can have this type of conversation is that you have a relationship built on trust.

Remember, if you're not willing to have a tough conversation, nothing will change.

Only you can decide what’s going to be best for you, what you value, and how you want to live your life.

Only you can decide what’s going to be best for you, what you value, and how you want to live your life.

2. Conduct an honest self-evaluation with these four questions.

With my boss now onboard, the next thing I needed to do was write things down and consider what it would mean to switch careers from all angles before we could take it up with other people at the company.

I realized that if I wanted a job that wasn't like my old one, I'd have to approach it differently. And that meant being honest with myself about what I was doing and what I wanted.

I didn't want to rush into something new only to find out it wasn't how I thought it would be.

So, what I did is use a modified version of the Japanese concept of Ikigai. Ikigai is a framework to help you define your overall life purpose. For this, though, I was just trying to figure out if a different career would provide me more satisfaction and fulfillment at work.

Ikigai asks, What are you good at, What can you be paid for, What do you love, and What does the world need?

To focus on my career, I adjusted it to What I am good at, What I am bad at, What I want to do more of, and What I want to do less of.

I figured defining each end of the spectrum would help clarify how I was feeling and give me a better perspective as I eventually would decide what would be the best fit for me going forward.

It's important to answer these questions honestly based on how you feel and what you believe. Not what you think you should say, what other's expectations are, or what anyone has told you before.

This is a self-evaluation, so now is the time to be selfish.

Likely, you don't like your current job because you did what other people wanted you to do instead of what you knew was right for you.

With that in mind, here's how you should think about each of these four questions.

What am I good at?

This should be an easy one. It's whatever you find easy that's hard for other people. These can be things that are directly related to the job you're doing now. Or something you don't get to do at your job but know you're competent at.

If you're having trouble coming up with examples, think about what other people tell you you're good at. And if you still can't figure it out, ask them.

What am I bad at?

This might be a little harder to define because we all want to be good at everything. But, knowing what you're not good at will help you identify what type of jobs you should stay away from simply because you're not innately suited for them.

These are things you struggle with. Things that take more time than you think they should—the type of things that seem to come easy for others that you have to work at.

What do I want to do more of?

These might even be things you're not doing at all now but want to start doing. Being able to say how you want to spend your time will help you qualify potential opportunities based on whether or not they'll allow you to work on these things or not.

What do I want to do less of?

This is probably the easiest of the four. These are the things in your current job that you for sure don't want to keep doing. Knowing what these are will help make sure you don't find yourself in the same situation again.

The key is knowing you won't get everything you want.

There will always be some things you have to do even if you don't like doing them. This is about finding a better balance and helping you do more of what you like and less of what you don't.

Once I'd answered these four questions, my boss and I met again to go over them.

Now, I had more details and specific examples of what wasn't working for me, my strengths, and what I wanted to spend more time on. Going over this with her helped me validate what I was thinking and check to see if I was missing anything.

From here, we talked about what disciplines I might be interested in that would maybe satisfy the things I'd written down. And, we picked four that I would look into more. This was helpful because it meant I didn't have to research everything. Instead, I could focus on things we thought had a high probability of being right.

The four we chose were Project Management, which I was doing currently, Account Management, Strategy, and Analytics.

As I research them, I listed out the pros and cons as well as wrote a paragraph on my feeling towards each discipline and why I thought it might be a good fit or not.

It was important to include Project Management as it’s what I’d been doing and would be the baseline for how I’d evaluate the others. And, I couldn’t rule it out entirely as maybe in doing this I’d realize it was the right job for me and what I wanted to keep doing but that I was at the wrong company. That’s not what ended up happening, but I don’t think I would have had as strong a perspective without it.

After I looked into these disciplines, my boss and I met to see where I was starting to lean and set up the next step.

When asking other people their opinion you’re not looking to copy what they’ve done, rather you’re looking for insights to help you make better decisions for yourself.

When asking other people their opinion you’re not looking to copy what they’ve done, rather you’re looking for insights to help you make better decisions for yourself.

3. Learn about different careers with these five questions.

Up until now, it's been a lot of self-reflection and research.

But, the next thing to do if you want to make an informed decision is to talk with people at various stages in the careers you're interested in.

This will help you know what you might be getting yourself into.

You don't want to change careers only to find it's nothing like what you expected. Or worse, exactly like what you were trying to get out of.

Unfortunately, many people don't know what to ask, so they just make assumptions.

They observe and think what they see is what they'll get.

But, if you don't talk with people and ask the right questions, you might find yourself in a new job where:

  • You're not challenged in the ways you want to be

  • There's more of the work you don't like doing than you thought

To make sure this doesn't happen, all you have to do is find a few people who will talk to you about their job for 30 minutes and ask these five questions to better understand what it's like.

And since you're looking to switch careers while staying at the same company, you have everyone you need to talk to right there.

After we had narrowed down what disciplines I was interested in, my boss had started to talk with other people at the agency who would need to sign off on me doing something else. So, at this point, it was easy for us to set up these informal interviews without having to hide my intentions as I could be completely upfront about what I was doing.

You don't want these conversations to feel like an interrogation, but you do want to get an overview of what this person does, along with some specific details about how they do their job.

These five questions do both of those things.

They're open-ended enough to let the person answer however they want while also specific enough to get you what you need.

Explain your job as if I didn't know anything about it?

Often, people try and overcomplicate what they do to make it seem important. But that's not going to be helpful to you.

You want the basics from someone who does this every day. You want to know what the expectations are, how it fits in with the company's other functions, what projects you'd be a part of, and when you'd get involved. All of these things you could probably infer, but you want to confirm by asking.

Also, by asking it to be explained as if you didn't know anything about it, the person might offer up some invaluable information they take for granted, but you wouldn't have any idea about it.

What are the primary skills and tools you use?

With this, you're trying to determine if any of the skills you already have line up with what the job requires. Of course, you're also figuring out what you're going to have to learn and whether or not that interests you.

Also, most everyone will say the tools don't matter, but if you find out what these are, you can start getting familiar with them before you need to use them.

Are there any frameworks you rely on?

Now you're starting to ask about the craft of the job.

By asking about frameworks, you'll get insight into different ways to approach various problems. If there are any best practices, you should know about, and generally how the work comes together. It's a good way to learn about the type of thinking you'll have to do in a new role.

Also, most of the time, people will use real examples to explain what they're talking about, which will help you understand the theory and how it's applied.

What do you not like doing?

I'd be willing to bet that everything anyone has said has been about the good parts of their job until this point.

But, no matter what, everyone has something they don't like doing. Asking this will help you get a sense of the less glamorous aspects of the job.

Also, they'll likely tell you what more junior people have to do to work their way up the ladder, which will be helpful as you learn what it takes to grow in this career.

Where do you learn from?

This shows you're serious and not just basing your decision on one conversation.

It also gives you something you can deep dive into on your own, whether they tell you about books, podcasts, websites, newsletters, Twitter handles, or whatever else. And, you're going to need to know where to go to find answers and information if you decide this is the path you want to go down, so it's helpful to get familiar now.

The best part about talking with these people is they become your peers.

As you wrap up these conversations, I'm sure they will all say you can follow up with them if there's anything more you want to ask or get their opinion on. This is important because these will be the people you end up working with if you decide to move into their discipline.

And, remember, the point of asking these questions isn't to copy what someone else has done. Rather, it's to give you more context so you can make an informed decision.


You want to develop compounding skills so that whatever you’re doing today continues to be more valuable over time.

You want to develop compounding skills so that whatever you’re doing today continues to be more valuable over time.

4. You want to do something unrelated but similar.

I call this Degree of Separation, which is how you balance the skills and knowledge you've already developed with the opportunity to learn something new.

It's what helps you start to qualify and narrow down your decision.

As you can see with the list of disciplines I was looking at, they progress from completely overlapping with what I was already doing to things further away from my existing skillset.

The point of this is to make sure you're not starting over. But you are instead becoming more valuable by choosing a new career where you can use your existing skills in new ways and have the opportunity to develop additional skills.

You want to find something that allows what you've done and what you will do to complement each other.

Finding the right balance.

I think the best ratio of new to existing skills is 60/40.

50/50.

I think 50/50 would leave you doing too much of what you were doing before. It would be too easy for people to expect you to split your time between your old job and your new job. And because you’re going to be better at your old job you’ll inevitably be expected to spend more time doing that instead of gaining experience with your new job.

60/40.

60/40 gives you enough new things to learn so you're challenged and feel like you're growing. While leaving enough existing knowledge, you can fall back on so you don't feel in over your head. This is important because you don't want to feel discouraged or like you’re falling behind. You want to create enough momentum so you always feel like you’re making progress.

70/30.

On the other side, 70/30 would mean you'd have to spend a lot more time training and would basically be starting over, which is what we're trying to avoid.

Of course, determining what’s going to give you a 60/40 split is going to be a bit subjective. But based on your self-evaluation, what people told you about their discipline, and opinions from those helping you out you should be able to have an idea of what makes sense.

Choosing your perfect job.

At this point, after you've talked with your boss about your desire to do something different, were honest with yourself about what you wanted, researched and spoke with people in other disciplines, and evaluated your skillset against what you'd have to do in different jobs.

You're now ready to make a decision.

Taking everything you learned, you need to think through what will be the best job you can have that'll put you on a career path you're excited about.

You need to think about your strengths and what you want to be doing more of and see what disciplines line up with that. And what you want to be doing less of, and rule out any disciplines requiring more of that type of work.

You also need to think about your existing skills and make sure some of them will still be relevant and that the new skills you're going to have to learn are things you're interested in.

And, you have to think about the future too.

Right now, you're focused on seeing if you can make every day better. This is important, but you also need to make sure whatever you get into next is something you can see yourself doing and being excited about for the long term.

Switching jobs like this isn't something you can do often, and definitely not twice at the same company.

You want to be sure the path you're about to get on is going to be worth it.

For me, this was moving into Strategy.

When I evaluated the different disciplines, we selected I knew staying in Project Management would continue to be the same, and I wasn't excited about where that would lead.

Many people thought I'd be good at Account Management, but I knew that it had more of the things I didn't like doing as a project manager just with a different focus.

And, while I love using data to inform decisions, the core skills of Analytics were just too far out of my existing skill set to let me go into that type of work without having to start over.

The more I researched and talked with people about Strategy, I realized a lot of the skills I'd developed as a project manager would easily translate to this new discipline.

Things like writing clearly, viewing challenges from various perspectives, managing different types of people, and putting together actionable plans that teams could execute on. All things that I was good at as a project manager were also indicators of great strategists.

And strategy let me be more creative, which was the one thing I wanted to do more of that I wasn't getting as a project manager.

This meant the things I needed to learn were new frameworks and understanding how things should happen from the strategy side. All things that are part of the craft and can be easily taught.

This overlap of skills made it an easy sell to my boss, the leader of the strategy discipline, and the rest of the agency executives who needed to sign off on this as they could see how things fit together and that it would be a win-win for everyone.

If you want to go fast, start slow so you can build up a solid foundation of knowledge and habits.

If you want to go fast, start slow so you can build up a solid foundation of knowledge and habits.

5. Three steps to successfully transition into a new career.

Now that I'd selected Strategy as the discipline I wanted to switch into and got the approvals I needed, the next thing we did was put a plan in place for how we would make the transition happen.

Obviously, I knew it wasn't going to happen immediately. All along, I'd been sure to tell people I didn't have any timing expectations other than I didn't want this to be something we stopped talking about.

I knew I was asking for a lot already, and demanding it to happen by a certain time didn't seem appropriate at all.

Mostly because switching disciplines meant they'd have to find someone to replace me who I would have to train, and then there would have to be an opportunity on the Strategy side that I could fill. So a lot of things had to come together to make it happen.

Everything up to this point had taken about four months—talking with my boss, doing my self-evaluation and research, and my informal interviews with people in different disciplines. However, switching disciplines ended up taking about eight months to fully transition once it was official that I'd be moving into Strategy.

So, about a year in total.

Doing it over this period of time was great, though, as I was able to gradually reduce my responsibilities as a project manager while building the knowledge and skills I'd need as a strategist.

Going slow like this meant I never felt in over my head and was able to build up my confidence and muscle memory, so by the time I was a full-time strategist, I was ready and didn't feel overwhelmed.

Most people, though, want to get thrown in the deep end to prove themselves.

You don't want to try and do too much too fast.

If you do, you might not build the proper habits as you rush to just get things done. And while you'll be taking skills with you, you have to realize you will be reorganizing and rebuilding your foundational skills. So it's important to remember:

  • It takes time to ramp up and get acclimated

  • No one expects too much from you yet

  • You don't want to make a mistake you can't recover from

I ramped up over time through these three phases as I built up my experience.

Doing it this way allowed me to set the right expectations and get the right experiences with the right people to prove I was capable in this new role and build up my knowledge and confidence.

Phase 1 - Orientation.

Before you officially start, you'll want to start getting acclimated.

This will likely be with your new boss or someone above you who can teach you more about the role. It'll probably be one of the people you had an informal interview with, most likely.

While your exploration conversations were about the role overall, these are more technical and get into the activities and deliverables.

For me, this was a weekly 1:1 where we would go through different examples of strategy work, an introduction to the tools I needed to know, and general discussions about what I should be thinking about and focusing on.

Phase 2 - Boot camp.

Most people think they can start once they know the theory, but it's never that easy.

You won't have an awareness of what to look out for just yet. So, you'll want to shadow someone on a project to learn and see how they do things. This will help you start to get a sense of what to look out for, where the roadblocks are, how to navigate project politics, the type of deliverables people will expect from you, and how to be efficient with your time.

I was lucky enough to work on a mid-sized project with one other Strategist who showed me the way and let me do some of the work with their oversight. This was great because I was able to apply what I'd been learning and get immediate feedback on what I had right and what I could do differently.

It's so much easier to learn by doing when the stakes are relatively low.

Phase 3 - Basic training.

Finally, once you've gone through orientation and shadowed on a project during boot camp, you'll be ready to start doing some of the work yourself. You won't be ready to take on an entire project alone just yet, but you'll continue to partner with someone on the team so you can keep learning while getting more and more responsibility.

And, most projects are often big enough that it'll never just be one person anyway, so don't worry about not leading a project for a while.

While this is a linear process, there's no set time frame you can expect for them to occur. You have to wait for the right opportunity to come up. And then every project is different and will take however long it needs to.

The point is to build up your confidence and muscle memory, so you know what to do when you're on your own.

The last question you need to ask yourself before changing jobs.

While it's exciting to think about getting a new job, you can see the way this works is to be intentional about how you approach it.

You don't want to rush into anything.

That's hard, though if you're to the point of thinking your current job is so bad, you'd literally do anything else.

If that's how you're thinking, then any opportunity to change is going to look attractive.

If that's you, all I want you to do is ask yourself this one question before deciding anything.

Is a new job going to be better, or just different?

Honestly answering this simple question will tell you whether or not you're excited about a new job because it's better than your current one. Or if you're excited because it's different.

If it's better and gets you closer to where you want to be or doing more of what you like, you should go for it.

If it's just different, you're probably better off making a plan to find something that's better.

Changing jobs because it's different just to get out of your current one has risks like:

  • A new job might have the same problems as your current job

  • A new job might not give you the fulfillment you're seeking

  • A new job might mean having to prove yourself all over again

Taking the first opportunity that comes your way is risky because you might end up in a worse situation.

I know this from my experience changing companies enough times to get out of where I was instead of finding something better to know it's not worth it.

Once the newness wore off, I was back to dealing with the same problems, needing to impress people I didn't know while feeling frustrated by my lack of progress.

So, again, is it better, or just different?


Wrapping up.

Changing careers isn't easy.

But after doing it twice now, I've developed this repeatable method for how to do it.

As you can see, the process is pretty straightforward, but it requires a lot of patience and confidence in your ability to navigate unknowns and have uncomfortable conversations.

The secret for all of it, though, is that you need to come prepared and be willing to put in the work.

You can't expect anyone else to take this seriously if you don't show how committed you are. That's why there's such a focus on self-reflection and research to make sure you're making the best decision for yourself.

This is why it's so rewarding to know you took control of your career when you're able to make it work.

You know you've done something for yourself that not only makes your life better, but likely everyone's around you as well.

Often, though, people stay in jobs that aren't right for them because they don't know that they can orchestrate a change. Or, they're held back from talking about it because:

  • They've been doing their job for so long they don't think they can do anything else

  • They don't know what it is they want to do; just that it's not what they're doing now

  • They're worried they'll have to completely start over

  • They're not sure they'll be paid the same in another role

But the only way to answer any of those questions is to start the conversation.

To recap, here are the five steps to change careers without starting over.

Step 1: Have a tough conversation with your boss.

This is critical. You have to tell your boss how you feel.

You can't expect them to know how you're doing or what you want if you don't tell them. Let them know you're looking for their help in figuring out how to make your time at work better by switching into a new role.

The key to this is seeding the conversation beforehand, so you're not catching them completely off guard.

Step 2: Conduct an honest self-evaluation.

Next, you have to do an honest self-evaluation.

You'll want to create a list of things you're good at, things you're bad at, things you want to do more of, and things you want to do less of.

This is what's going to guide you as you explore different careers you might be interested in.

Step 3: Explore different careers.

Next, you want to do your own research and have exploration conversations with people in different disciplines to see how your self-evaluation lines up with the work they do.

You want to get a sense of what these different careers are actually like from the people who do them.

Step 4: Choose something unrelated but similar.

With all of the information you've gathered, you're now ready to decide on whether or not you're going to stick with your current job or if you want to do something different.

If you're going to change careers, you want to pick something that gives you a 60/40 split between new things you have to learn and your existing skills.

Step 5: Gain experience and build your confidence.

Once you've done your research and identified what new job you want to transition into, you and your current and future bosses can then start to develop a plan to make it happen within the company.

Doing this in a phased approach will allow you to ramp up into the new role and not feel like you have no idea what you're doing.

I know changing careers will never seem as easy as I laid it out here, but know it's possible if you follow these steps and are willing to put in the work.

And, remember. If you don't decide what you're going to do with your life, someone else will decide for you.

If you have any questions about changing careers or want to learn more about lifestyle design, follow me on Twitter @wesjonesco.

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