How to Include Personal Stakeholders (i.e. Family) in Your Career Journey

Sometimes, it takes time to get to where you want to go.

In the last few months, I have struggled to speak with family openly about my UX job search, as well as the impact it has had on me both mentally and physically.

While I have pushed hard on the networking front — scheduling calls, sending cold emails, attending MeetUps, completing design challenges and also reaching out to additional professional connections — I am still pushing forward towards this unknown design future.

Living in New York City is a hustle — many folks whom I know personally work “side hustles”, which are additional freelance projects that help keep them afloat on top of their day-to-day career.

But what about the people looking to break into an industry that is budding, without a clearly-defined path to entry that will lead them to their first role?

How might we hustle without gaining the experience that we need to be qualified for that hustle? It relates to the conundrum many in the job search face: you need experience to get the additional experience.

As aspiring designers looking to solve for this problem, we need to first research the industry, avenues where we are able to take part in it and then continue efforts to grow our expertise in the field. All of this is to fulfill our goal of a better career experience and professional life.

Speaking for myself, I worked in New York for almost three years within the marketing space. Overtime, I came to feel that my role lacked additional creativity and I had taken multiple steps within the industry to move into the product space with limited success.

Speaking with a former coworker whom also debated the merits of a career in product, our conversation helped guide me towards researching design as a career, as well as the options that were available to educate myself towards a career in that space.

I spent the next six months silently researching product design, careers in UX and the cost-benefit analysis of exploring a career industry pivot at the age of 28.

Being based in the US, I looked to relevant tools that might help inform my decision. I consulted the US Bureau of Labor Statistics to find statistical data regarding those working in design and computer science. Looking at the numbers, it seemed that a career in design — if I pivoted successfully — could help me become more financially comfortable than where I was at the time. Additionally, the growth opportunity in this market was growing nationally, thus it made sense in my mind to hop in and explore it.

I now had to take this career market data — the interview insights, quantitative data, and educational options — to my primary stakeholders: my family. I could not personally embark on this journey financially and I also wanted their personal support in this experience towards a better career.

Before I continue, it is important that I clarify that I am writing this article because I wanted to provide those of you who have traveled this career-changing road with scenarios where you can engage with these personal stakeholders. These individuals whom you rely on for guidance want nothing more than to be involved in your life, to see you succeed within it and to help steer you towards new opportunities that can benefit your future.


Understanding Professional Upbringings & Career Timelines

First, my biggest advice to those on this adventure is to remember the following: We (Millennials, Gen-Xers) are growing up in a world of constant, ravenous change — more often than not, these economic changes have impacted us negatively compared to other generations.

We (again as a collective, career-wise) are not standing on a hardwood floor as much as we are at sea, staying afloat for the next island or lifeboat we find.

Those who have cheered for us and our growth into adulthood are now older (generally in their 40s, 50s, or later) and while they encountered a career environment that was changing quickly, the economic outlook that they grew up in was also much more vibrant than what we have experienced today, which has allowed this generation to continue to thrive compared to their younger counterparts.

Diving deeper in terms of the history of hiring practices, technological advances during these decades were less nuanced, the barrier to entry was lower and a lack of powerful e-tools limited the extreme fluctuation of qualified candidates looking for work or being recruited into positions.

As a result of this, the frustrations 21st century digital boys and girls might feel in terms of looking for design (and tech) work is now the new normal; the path towards these opportunities are simply not linear.

Going back to your personal stakeholders, this direct overview may be hard for them to understand (they’ve worked for your success, after all). Remember, in their career development, the path towards career success was more straightforward than it is today.

Today’s economic outlook is a landscape that is consistently changing — it is a brave new world to those who began their careers in the 1980s and 1990s, whereas it’s a challenging new world for job seekers.

Let’s expand on the prospect of recruitment. Prior to the growth of computers, mobile phones and the launch of the world-wide-web from the late 80s to early 90s, job candidates would connect with recruiters via phone, fax, and even US mail.

Today, job seekers — the users in this case — are dealing with a behemoth of tools at their disposal. And it is not just them: recruiters and other hiring professionals have these tools at their disposal as well.

In searching for “UX Designer, candidate A”, individuals are able to surface candidates B, C, D, E, F — all the way to M+, as an example — by using tools like LinkedIn, AngelList, or Indeed.

The hiring game has changed and adapting to the advances of technology is not only a benefit but it can also be a deterrent in getting you hired immediately, as unfortunate as that might sound.

How one might feel in the midst of today’s hiring process — a process that is different for every company (i.e. processes might include: phone screens, interviews, whiteboard sessions, design and even coding challenges).

Looking back once more to your relationship with your stakeholders as you navigate this voyage, be sure to keep them in the loop of what you’re doing in order to enter this space. Reiterate to them that this is a field that is consistently changing — just as the economy is consistently changing.

As someone who has a passion for history apart from UX (as well as being a present-day job seeker), I often reflect on the progress that has been made in the last century regarding technology, innovation and automation.

In the early 1900s (and really before then, with the launch of the Industrial Revolution), skilled laborers started to be replaced by mass-production assembly lines and general workers. The hours these workers worked were excessive and it was not until the innovation of the eight hour workday that modern day office structures eventually took shape over the coming years.

Work used to be a lot harder, albeit today, it’s also a lot harder to find it.

Think about that progress which has overall remained the work standard in the 21st century (I say roughly, as many of us have worked above that 40 hours per week mark). To bring this overview “closer to home”, let us look at a more modern example from the last ten years.

Take the phone manufacturing company Blackberry. In 2009, BlackBerry and its smartphone OS held near 20% of the smartphone market and now, companies like Apple are eating their lunch. Apple and its iPhone hold 18% of that same phone market in 2019 based on their own innovation and technological advances to the handset.

The two “big” phones of 2008 — the BlackBerry Storm & original iPhone 2G.

The iPhone has seen radical hardware and software iteration changes in the 11 years since the phone has been on the market. I won’t even start on the software shift from skeuomorphism to flat design.

My original iPhone 2G of 2007 compared to my iPhone X from 2017.

So what point am I trying to communicate with these examples? It is that industries throughout the world in the 21st century are changing at an exponential rate. Life as we experience it is changing very quickly.

This realization is critical for your supporting stakeholders to understand and accept as you begin navigating this career future and its possibilities.


Think Like a School Teacher: Show Your Work

As I talked about in my last Medium article about “UXing” your interview process, by showcasing your design work and UX process to the interviewer, you will demonstrate your value first-hand to the company considering you for an open position.

This same principle applies to those who are your advocates — and it can be difficult to address.

Considering the likelihood that you are living on your own (i.e. roommates, significant others, doggo), you want to be sure that those who are here for you outside of your immediate support system are clued-in to where you are in this process and what you have been doing to make an impact.

How are you working towards making a positive change in your life? You need to be your own advocate and champion in this process.

This is going to be hard but you’ll need to be your own champion to keep fighting through it.

These conversations might be difficult to have (and they may not provide any immediate resolution in your relationship to your stakeholders) because this concept will feel foreign to those who grew up in the stabilized economy and career timeline of years lore.

Here are some sample questions that you might be asked by your stakeholders during your career journey:

  1. Why aren’t you applying everywhere (this might occur if you’re already predisposed to a particular location)?
  2. Why are you only looking at these types of [list role name here] jobs?
  3. Why don’t you go back to your old company or role?
  4. Why haven’t you found anything yet?

Unfortunately, when it comes to this, I cannot advocate for you. What I can suggest, in terms of your UX journey, is that you do everything in your power to make yourself known in the design community.

Go to MeetUps, schedule coffee dates, attend industry-led expert panels to learn from others who know more than you, write on Medium (if I can do it, why aren’t you?) — you are your own unique person in this universe, there is no other you, so make the world know who you are.

Any connection you make can lead to a conversation. A conversation can lead to an opportunity. An opportunity can help you land an interview for a role towards your own contributions in this field. So get out there and do it.

Whenever I have engaged in these opportunities, I try to highlight my process and do as my seventh grade math teacher told me: show your work.

Show the people who care about you the article you’ve written, tell them about how it was received by the community, show them the design challenge you just submitted (which you will ace, because you’re amazing) and explain to them about how you’re approaching this field by seeking opportunities to grow and be of value to others directly.

Show your work, y’all, and make your voice heard!

Sure, you want a UX job (same!) but the world does not cater to you. You must respond to the world and the signs you are receiving within it. If it feels “right” to speak with someone, do it. No one will fault you for putting your best foot forward but everyone will shun you for not taking the initiative that is required to grow.


This Is A Chapter In Your Life’s Book — It Will End.

While this might be hard for some to face during their search, it is important to remember that this experience is but a chapter in your own book of life. It will end. You will grow, advance and you will not be in “limbo” forever.

Recall that I am telling you this as someone who understands where you are. This is difficult advice for even myself to listen to but it is the truth — nothing lasts forever.

As I am also navigating this journey, I know how hard it can feel. You have invested the time to learn a new skill, you have practiced it, you have written about it, and you have made an effort to take part in the industry community. And still, you are putting your best self out there in search of that first role.

Sometimes, it is just hard to realize that however long you have been in this state — a week, a month, a year — that it is temporary but take solace in that. Reach out to your friends and schedule a night out.

Do not seclude yourself entirely while you’re on this journey. Time for yourself is good but be sure to spend time with your friends, they will lift you up (note, 80’s themed outings are entirely optional)!

Have a wine-and-dine move night with your significant other (or doggo — can you tell that I think that dogs are just the best?). Be sure to also schedule a good workout with a friend to improve yourself physically, as well as mentally.

Do not be a Lemon — outings with others are much better, highly encouraged, and can reinvigorate you!

Remember this: you’re human and this process can be exhausting, so please make sure to take time for yourself.

In a time like this, you need to know what your triggers are. Did you have a day where you found it challenging to network, connect with others, showcase your value, or send out applications galore?

That might be your body telling you to hit the “snooze” button and take a rest. That is not a bad thing — I repeat: that. is. not. a. bad. thing. What you’re working towards is a mental marathon versus a physical one and that can take a toll, so be sure to get plenty of rest when and if you can.

Time for yourself is also encouraged, understandable, and needed (it’s up to you if you like seltzer and reading as an activity, though).

At the end of the day, this entire experience will have helped us (you, me, others) grow. It is a learning experience.

Unfortunately, not every adventure we encounter can mimic The Wizard of Oz. We might not get to be like Dorothy and simply “follow the yellow brick road” for our future professional success.

We have to remember that this experience is not linear. Not all roads are gold, not all roads are paved and not all roads have been traveled.

All we can do is put our best self forward — and share that with those looking for our skill set, as well as those who believe in us — to achieve the professional future that we studied and dreamed to call our own.

Your friend in UX, Diego

UX Yourself, or “What’s Your Story?”

After entering the UX Design industry in Spring of last year, I had thought I had gone about navigating the job market rather well.

Summer and Fall came quickly, and all I did during those months was regularly tweak my résumé towards my applications, attend tech MeetUps, LinkedIn message individuals in companies of interest, make connections with alumni of my UX program (and college), as well as schedule countless calls and coffee dates. All of this provided me great insight but I was still left thinking, “What else can I do to stand out and from the design crowd?”

Recently concluding a teaching and support role for a full-time and part-time cohort of General Assembly UX students in New York, I was hungry to freshen up my search efforts but wondered what I could do differently to advance more quickly.

This is me. I am User Flowing at the moment.

A month or so ago, I asked one of my mentors to dinner after work. I wanted to gain his feedback as someone yearning to formally enter this field beyond the classroom. I wanted his insight as to how might I demonstrate who I am and what my value is to those operating in this field.

He sipped his wine and took a moment to pause and reflect. His advice was the following:

“Think of your personal brand as:

How do you learn?
How do you think?
How do you approach this work?”

Put more simply: by demonstrating what you know to be true, others will see the value that you bring to this field.

We drank our wine, munched on our fries and wished each other a restful weekend. I left our meeting puzzled about how I should act on those words and decided to let the conversation sink in as I took an Uber drive home.

I had not yet understood how to take this insight to heart but I would and very soon.


As our cohort ended and a new group of young designers prepared to enter the field, I began to double-down on my efforts in terms of UX networking and projects.

Recently, I had traveled to my parents for a quiet weekend at home. It was warm, sunny, and I was studying for upcoming interviews. I already had a dedicated notebook full of details from company websites, job postings, online presentations, recruiter YouTube videos about navigating the corporate interview process and I had even looked at what tools some of these companies offered that I could familiarize myself with should it come up in conversation.

Still I was left wondering: “How else can I demonstrate my value, and what I know to be true in this field, beyond the standard interview?”

Then it hit me. UX — User Experience Design — is not confined to a computer screen, it is all around us. It showcases itself in the machines we use, the applications we navigate, the cars we drive, the elevators we ride to reach our office floor — heck, it’s even in the unorganized restaurant menu that you have to read through at brunch to find your favorite meal.

Everything we interact with has been designed and engineered to elicit a response from those using it. We are the users of our everyday lives. So why not combine the craft of UX with navigating the ambiguity the job market and candidate interview process?

Why not UX myself — showcase my career journey, what I have worked on, how a company’s goals are aligned with my own, and the value I can provide as a UX Designer — in a brief and thoughtful presentation for the interviewer?

Wondering how to go about this? Great. Let’s get started.


1. Where Have You Been Before?

Your Professional Journey is its own adventure — share it!

From personal experience, the majority of designers I have met did not simply come into UX. They all had their own unique journey into the field — I have met folks who came into UX from web development because of the needs of their company, whereas I came into design from the marketing industry.

Wanting to showcase my own unique career path, I wanted to provide a visual frame of reference for those considering my candidacy. While a recruiter or hiring manager might look at my résumé, this did not necessarily capture my journey holistically.

Thinking of how best to navigate this, I concluded that showing an overview of myself and my career journey, similar to the structure of a UX “Persona”, would be a great starting point. I provided my career trajectory as a visual timeline, with company logos, a head-shot of myself, my professional certifications, and a quote about what I believe is important in the design space.

While the person speaking with you in your application process might know who you are based on your résumé, LinkedIn profile, or Portfolio, this visual gives them additional context into you as a professional creative strategist.


2. What Is Your Value?

While interviews usually gravitate towards the why behind your application (i.e. why do you want to work at ______ ?), you have the opportunity to provide the company with an overview of what their goals are and how you can address them with your professional expertise, willingness to take on challenges, and eagerness to solve problems.

Start first by breaking down the core company goals and comparing them to your own professional ones. Map them out and demonstrate where you can both align. Demonstrate what you know to be true about the company and what you know to be true about yourself, as well as the value that you can bring to their team.


3. What Have You Done?

A summary of Portfolio pieces makes it easier on your audience to get a snapshot of your work.

Those working in this field and hiring for it often want to understand what work you have done in the past, as well as your design process in order to deliver a solution. As this is a story about you, think of this component as the “highlights reel” of your work — what portfolio projects can you summarize and demonstrate knowledge in? Think about the projects that speak about you, your UX process, and the problems you have faced as a designer. Hyperlink these works — make them a click away for that curious someone to dig deeper into your deliverables.

Finally, in this summation (think 2–5 sentences) you should note the impact of what you have done. Did your solution solve a problem? Great. Did the client execute your research considerations? Even better. Will your work be used by others in the organization you provided services for? Amazing. Bring these gifts of yours into the conversation and let it highlight your professional value.


4. Wrapping Up — Be Confident.

The next step in this process should be your closing statement, as you want to be empathetic regarding the interviewer’s time constraints and need of filling this role. You have already shown your initiative by compiling this deliverable for their review.

If not now, this work will be valued by others considering you for their organization — you’ve shown the initiative and drive, it’s now up to others to decide as to next steps.

In ending this overview, explicitly tell them how your personal brand will have an impact on their company for the better. In two sentences, tell them why do you want to be here and how will you put success on the agenda. Keep it short, keep it sweet and be confident in your statement. After all, the statement — as well as this document — are a part of your personal brand.


5. Contact Information & Sources

This is the easy stuff. Provide your contact information (phone, email, LinkedIn, Portfolio, etc.). Literally make the lives of those considering your application easier by providing immediate avenues to your creative works.

Lastly, it is highly likely that you used the company website, online resources, and additional tools to bring this overview to life. Site them. Demonstrate to those around you that you believe in providing credit where it is due — this can be carried over in understanding how your success as an individual does not stem solely from yourself but from your team.


So, did this extracurricular UX project sound like a large undertaking? Yes. Did this take me out of my comfort zone? Yes. Do I regret it? Absolutely not.

This “UX-ing” of my interview process forced me to evaluate what drives me professionally as a designer, as well as what I can uniquely offer to others if brought onto their team. If anything, this process helped me feel more secure in preparing for upcoming interviews because it forced me to really expand on the why behind my applications.

Honestly, it is not that I need a formal UX role (but yes, that would be nice) but it is that I want experience in this field where what I know to be true — and what a partner company knows to be true — can align for us to work together towards solving business problems for others.

I hope that you all will find this overview helpful in your own journey and I thank you for reading.

— Your friend in UX, Diego