Your Future (Work) Self

For reentry employment planning, I like to use five years. A goal is set five years out from the beginning of the reentry process and then reverse-engineered back to the present.

“This five-year goal includes the work you want to do, where you’d like to live and the person you want to be.”

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In reentry terms, it is a long-term goal. In life terms, it is a mere chapter in someone’s personal story.

That’s reentry, but the idea works equally well for those changing careers or starting out, say, recent grads. It’s helpful to visualize the attainment of this goal—to see your goal, yourself achieving it, and the route you will take to get there. Visualization of this type is used successfully in sports psychology, business, health and wellness, and many other areas.

It's all good, but I want to focus on the path taken—the route. Setting the end goal and seeing yourself reaching it in a mind video isn’t that hard for most people. The route to get there, however, can be another matter. Surprises always happen along the way; this is where most of us swerve off the road and lose out on achieving our goal.

What follows is a simple exercise designed to narrow down the route to your goal, the trickiest part of this type of planning.

Step 1

Start with your five-year goal and, using thoughtful best-guessing, list in reverse order three or four jobs you think you will have from your goal to today. Consider each job to be 12 to 18 months in duration. Add details to each role, but don’t get hung up on this step.

Step 2

Repeat this process, but start from today and work forward to your goal. This time, include more details about the duties you will perform, the team you will be part of, the size and location of the company, etc. Think more about the duration of each role, adding start and end dates for each. This list should look like your work history listed on your future resume.

Step 3

You now have a sequential list of the jobs you will have, each a progressive step toward your goal. To move from one to the next, you will need references from people with whom you have work relationships. Ask yourself, “Who will I need to connect with at each job to help me move to the next?” Imagine who these two or three people might be and list them in Step 2 for each position.

Step 4

After reviewing your list, put on your best-guessing hat again and jot down things that could happen during each job that would challenge you to get to the next. Be creative here, but keep it real! As noted above, this is where many plans fall apart. Unanticipated and unexpected things make it hard to progress to the next job. Think deeply about this step.

Step 5

Look over what you have created. You now have a route map with dates and details covering the jobs you will hold from today until you reach your five-year goal. You have thought about the people connections you will need to make and some possible things that could require adjustments and workarounds to stay on course.

~ ~ ~ ~ ~

Why go through this exercise? There are many good reasons; here are a few:

The first reason is to visualize the route, not just the end goal, with you giving yourself an attaboy/attagirl pat on the back. Instead, you’ve created a first draft of your personalized job roadmap.

The second drives home the importance of defining your starting point on this journey: your first job and your Job Search Objective. Needless to say, starting off on the right foot is crucial; that’s why having a Job Search Objective is non-negotiable.

The third reason is that it transports you from visualizing to actual planning. Sure, it is a draft, but it is your draft. You own it. In a way, you are now like a startup. You have a goal, a plan, and a starting point. You are prepared to make course corrections and small pivots along the way, but you intend to stay the course and reach your goal.

Reentering, transitioning careers, or just starting out—you, the startup, are ready to launch.

PS - This exercise exemplifies something many might consider but never do. However, folks reentering, transitioning, or panicking about starting out, on the other hand, are sometimes freaked out enough to dive in and imagine the route needed to reach their goal. They do it, and they benefit. They are one step ahead and more aware of what might lie ahead.

Onward!

People Escalators

While researching the importance of first jobs, an article in Forbes caught my eye: The Impact Of Your First Job After College. Although I wasn’t focused on jobs associated with recent college grads, the article offhandedly reinforced my perspective that reentry success starts with the “right” first job.

The Forbes piece points out that career progression for aspiring college grads does not favor switching paths. This is partly due to online hiring algorithms that can pigeonhole candidates and applicants into similar roles as they move forward, making it challenging to explore diverse career opportunities.

To quote the article,

“These algorithms, while efficient in processing large volumes of applications, often lack the nuanced understanding of your potential beyond your immediate past experience. They often overlook transferable skills or the ability to adapt and excel in different contexts.”

So, how does this correspond to reentry and the all-important first reentry position?

• First, it is ANOTHER reason to seek the right first job—to pigeonhole yourself intentionally! After all, a unique Job Search Objective aims to position you to penetrate and move forward in a specific field. You want future employers to see you in this light. If a hiring algorithm shepherds you along this particular career lane, okay!

• Secondly, being a pigeonhole-ee aligns with your longer-term plan based on remaining in a chosen field. This is not to say minor deviations and role pivots won’t happen; they probably will. However, these course corrections will occur within your selected field vs. moving to an entirely different category of work.

Generally, more efficient digits (AI algorithms) will not make things easier for the background-challenged job seeker. More sophistication will translate into new ways to eliminate candidates well before meaningful engagement. Furthermore, altogether avoiding online applications and evermore savvy candidate tracking platforms isn’t possible now and will only get more challenging. When some facet of new technology drops in your lap (like pigeonholing), recognize it and take full advantage.

Still, the best search plan is based on face-to-face interaction with prospective employers and hiring managers. It reduces the impersonal negatives of the online application process, which is particularly important when mapping out your first reentry position. Your Job Search Objective gets you in so you can do the work, make modest progress, and move on to your next role.

See this first job as getting on an escalator—not any escalator, your personal one. You have to do the work to retain your spot so that you can move up to the next floor. Your task and responsibility is to stay on this industry-specific set of escalators, progressing from floor to floor.

My reentry approach, as outlined in my book Get Beyond Your Troubled Past, is designed to avoid the digital hiring ecosystem as much as possible. My way demands more—it is not the shotgun, resume blast-out method. I emphasize connecting with people thoughtfully and strategically. Imagine that, people, live humans, not bots!

These people will become your personal escalators.

Successful reentry begins with getting your head straight, planning, and developing your Job Search Objective. And it very much involves connecting with people. What’s more, the bigger your pile of background challenges, the MORE you need people. Understanding and accepting this is part of getting your head straight.

Onward!

Engagement and Motivation

According to Gallup’s State of the Global Workplace: 2024 Report, 67% of US employees are not engaged with their work or jobs. Here’s the breakdown and comparison to global stats:

• Engaged: US = 33%, Globally = 23%

• Not engaged: US = 51%, Globally = 62%

• Actively disengaged: US = 16%, Globally = 15%

So, compared to all the countries studied, work engagement in the US is marginally better, but still, 67% are not excited about their work.

Why?

There’s no single answer. Some factors include remote work, lack of role clarity, turnover, lack of training, and sub-par management. There are undoubtedly many others—and frankly, this is an essential issue with a societal impact that always lands below the fold.

So what motivates the average worker, noting that most are not engaged in their work?

Compared to years past, it does not appear to be tenure, something most of us have seen or experienced anecdotally. From my experience, it varies by individual and industry. That said, the list always includes some or all of the following: salary, bonus potential, benefits, advancement potential, company culture, opportunities for professional growth, and work schedule flexibility/PTO.

Okay, so on balance, US workers are not (very) engaged, aren’t expecting long-term roles and are motivated by the things listed in most job descriptions.

Fine. So, what does this have to do with reentering job seekers?

First, there’s a need for workers—this is good. Furthermore, turn-over rates, especially for entry-level service positions, are high, which is another good thing because the first goal of any reentering worker is to GET IN.

However, once a reentry position has been secured, engagement and motivational considerations will differ from those of the average worker. Four things are critical for the reentering worker on their first job back in the workforce:

• Stay in

• Develop work contacts

• Build work history

• Prepare for the next job

This first reentry job is not a forever job—it is short-term on purpose, and job description attributes are accepted rather than negotiated. But engagement? There is no option here; it is a MUST!

Other employees may or may not be engaged, okay, but that does not apply to the background-challenged, reentering person!

And something else. Too often, after a reentering person has settled into the new role, say 3-5 weeks on, it’s easy to start forgetting why they are there. They associate with and begin relating to the other workers who aren’t reentering. They want to belong. Their original motivations (get in, stay in, develop work contacts, build work history…) seem trite.

“Hey, like everyone else, why not think big(ger), more money, bonuses, and advancement?”

No! A MAJOR MISTAKE. Don’t go there.

Keep the focus on the work and plan.

Stay the course. Fit in, but just enough.

Onward!

Workplace Dynamics

Experiencing success in the first reentry job is crucial. It is, quite literally, the foundation for all future work-related endeavors. If the job seeker has taken the time to outline their Job Search Objective, they know that landing this initial job was not random; instead, it is part of their overall work/life plan. Furthermore, they know this is not their forever job, that it’s an entry point where they start.

Once this position has been secured, the focus shifts from getting it to keeping it. At this point, the objectives are doing the work, achieving modest workplace success, and building work-related connections. Superstardom is out, as is coming in last. For most reentering folks, solid, stable, consistent performance works best.

But there’s so much more happening on this first job besides the work itself. Beyond accomplishing assigned duties, there will likely be many situations that require heads-up navigation. Just doing the work can be the least demanding part of succeeding.

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Here’s a list of 15 challenges related to workplace culture and dynamics that can trip up someone's success at their first reentry job. These types of situations could, of course, impact any worker. However, they can be particularly harsh for those with background baggage. Therefore, taking a 360-degree view of all that could happen is the right preemptive move.

1. Stigma and prejudice: Colleagues may hold preconceived notions or biases about individuals with criminal records or addiction histories.

2. Trust issues: Coworkers and supervisors may hesitate to trust an employee with a troubled past, especially in roles involving sensitive information or financial responsibilities.

3. Social exclusion: Employees with background challenges might be excluded from social interactions or informal networking opportunities.

4. Overcoming imposter syndrome: Feeling like they don't belong or aren't worthy of their position can be particularly acute for those with troubled backgrounds.

5. Navigating workplace politics: Understanding unwritten rules and power dynamics can be challenging, especially if previous experiences were in very different environments.

6. Communication barriers: Adjusting to professional communication norms may be difficult, mainly if past experiences were in less formal settings.

7. Handling workplace conflicts: Resolving disagreements professionally might be challenging if past coping mechanisms were unhealthy or aggressive.

8. Dealing with triggers: Workplace stress or certain situations might trigger memories or behaviors related to past struggles.

9. Balancing disclosure: Deciding how much to share their background with colleagues can be a constant source of stress.

10. Performance anxiety: Fear of making mistakes and reinforcing negative stereotypes can lead to excessive stress and underperformance.

11. Adapting to structure: Adjusting to workplace routines and hierarchies might be difficult, especially after incarceration or unemployment.

12. Managing time and priorities: Balancing work responsibilities with ongoing recovery or legal obligations can be challenging.

13. Handling feedback: Constructive criticism might be perceived as personal attacks due to heightened sensitivity or past experiences.

14. Building professional relationships: Forming trusting, professional bonds with colleagues and supervisors might be difficult due to fear of judgment or rejection.

15. Navigating technology: Depending on the length of absence from the workforce, adapting to new technologies and digital workflows could be challenging.

My approach begins by helping each reentering person see themselves as a Free Agent, Selling their Service in the Marketplace. Absorbing these concepts assists with achieving their Job Search Objective by landing the right job -and- retaining and advancing on this most essential step in their work/life plan.

The importance of preparing for a full range of developments and difficulties during this first job is hard to overstate.

Things are sure to come up.

Stuff always happens.

Plan for it.

Onward!

Imposter Syndrome

As a job seeker with a troubled past, have you ever felt like you're wearing a mask, pretending to be someone you're not? Do you often doubt your abilities, worth, or right to succeed despite evidence to the contrary? If so, you're not alone. Imposter syndrome, a psychological phenomenon that affects countless individuals, can be incredibly potent for those with challenging backgrounds.

Imposter syndrome is characterized by an overwhelming sense of self-doubt and a fear of being exposed as a "fraud" despite tangible accomplishments and skills. It's a nagging voice in the back of your mind that whispers, "You don't belong here," "You're not good enough," or "It's only a matter of time before they find out you're a phony."

Imposter syndrome can be particularly tricky for job seekers with troubled pasts. You may worry that your background disqualifies you from specific opportunities or that others will judge you harshly if they know about your past struggles. You might dismiss your strengths and capabilities, chalking your successes to luck or external factors rather than your efforts.

Left unchecked, imposter syndrome can sabotage your job search and career aspirations. It can lead you to self-select out of promising opportunities, avoid putting yourself out there, or undermine your performance due to a fear of failure. It can trap you in a cycle of self-doubt and stagnation, preventing you from realizing your full potential.

However, it's crucial to recognize that imposter syndrome is a distortion, a false narrative your mind creates to protect you from the discomfort of growth and change. Your past experiences and challenges have likely equipped you with unique strengths, insights, and resilience that can set you apart in the Marketplace.

One of the keys to overcoming imposter syndrome is to start reframing your internal dialogue. When you catch yourself engaging in negative self-talk or discounting your abilities, pause and ask yourself:

• Is this thought accurate? Is it true?

• What evidence do I have to support or refute it?

• How might I view this situation when talking to a friend or loved one?

By questioning your self-doubts and practicing self-compassion, you can start to chip away at the power of imposter syndrome. You recognize that your worth is inherent, not contingent on external validation or perfection. You begin to see your background as a source of strength and unique perspective rather than a liability.

Another effective strategy for combating imposter syndrome is to focus on your value to potential employers rather than fixating on your perceived shortcomings. When applying for jobs or preparing for interviews, reflect on the specific skills, experiences, and qualities that make you an asset to the role and the organization.

Consider creating a "brag sheet"— a list of your accomplishments, strengths, and positive feedback you've received from others. Review this list regularly to reinforce your sense of competence and worth. Practice speaking confidently about your abilities and the results you've achieved, even if it initially feels uncomfortable.

Imposter syndrome originates in your mind as a thought and is related to fear—not real fear, as in,

“OMG, there’s an enormous tiger in the next room, and he looks hungry!!!”

Instead, it’s imagined fear about something that could happen (later) but isn’t happening (now). No one else can see, feel, or touch this imagined state, but they can see the byproducts of it, such as how you act, the body language you display, and the words you use. Imposter syndrome exists only in your mind. Don’t give it any power by manifesting these behaviors.

So, how do you deal with imposter syndrome as a reentering person? You manage it.

• Trust the reentry process and your employment plan.

• Stay focused on doing your job to the best of your abilities.

• Act the part and fit in, but avoid comparing yourself to others at work.

• Stay away from work drama and complicating interpersonal distractions.

• Be punctual, dependable, and consistent—maintain a strong work ethic.

Ultimately, overcoming imposter syndrome is an ongoing practice, not a one-time fix. It’s a process, just like reentry in general. Keep in mind that you secured this job because you had a Job Search Objective, and you achieved it. You positioned yourself and were selected just like the other employees. You are there to do a job, which is the only reason you know the other employees. You, your plan, and doing the job come first. Be friendly, personable, helpful but not needy. Carry your own water, do the work, and find success. Doing this consistently is the best medicine for an imposter syndrome ailment.

By learning to recognize and reframe imposter syndrome, you liberate yourself to pursue your career goals with greater confidence, authenticity, and tenacity. You begin to see yourself not as an imposter but a capable, valuable contributor with a unique story and a bright future.

Remember that imposter syndrome is a shared experience among highly successful individuals. Many people you admire—for real—grapple with their self-doubts and fears of inadequacy. The difference is that they've learned to recognize these thoughts as false narratives and to keep acting despite them.

Onward!

Work Journal

In the best of all situations, each reentering person has a Job Search Objective (a plan detailing the specific type of job they will initially pursue) and a longer-term plan, say five years, outlining the positions they would like to hold beyond the first.

Once they secure their first job, the focus shifts from search to retention and preparation for advancement. The second reentry phase begins here, keeping, doing well, and progressing on this initial job. Sadly, this is where things often fall apart as the programming spotlight fades due to funding limitations or lack of proper hand-off to another related program or service.

But the spotlight fade is a topic for another time. I want to discuss a tactical tool used to support this second job retention phase: the work journal. Of course, maintaining a work journal is hardly specific to those reentering. Nonetheless, this type of journal can have significant benefits for those reentering.

However, a disclaimer of sorts is in order. As enthusiastic as I am about keeping a work journal, it can be a bridge too far for someone reentering with an extra full plate. Therefore, this is entirely discretionary. That said, I certainly recommend including it in the phase two tool bag. Set the stage and put it out there, but don't assume you know who will take to it or how they will (or should) use it. Encourage it, support it, and see what happens.

Here's how I present it to those reentering.

Gather the details

Starting from day one, document your job's specifics: the job description, your work schedule, assigned duties, the people you work with, those that supervise you, things learned, difficulties faced, surprising things, unexpected things, etc. Include the date and the day of the week for each entry.

Record the details

Start by writing about your (own) work story like a journalist. Focus on specifics and facts. When it's time to vent or ruminate, label this "Personal Note."

For each entry, start by writing your journalist recording. You may not have a personal comment about some entries; that's fine. But to make a personal note, you need a subject (your journalist recording), so make sure you have one. Doing this will help keep your journal entries associated with your work.

• As a journalist, you write what (actually) happened.

• As a personal commentator, you list how you felt about it.

Write often

Make a daily entry, a few paragraphs, or just one sentence. Get in the habit of recording (something) often and consistently.

Writing comes first, format second.

The most crucial point is this: Use a format you already know, the one you always use. Word or Google Docs, notes on your phone, handwritten in a notebook—all will work. What's important is doing it, writing journal entries. What device or format you select is up to you. Remember, though, that you're writing these notes for later use. Be organized and methodical in how you keep your journal.

How to use it

Your first job (removing stupendously rare situations) will not be your forever job. The goal is to advance in it and from it. Your work journal entries are what you use to prepare for an evaluation and when updating your resume. You need a factual record of what you did (in detail), how your duties changed (if so), and what you did to help move the business forward.

A cautionary note: After a month or so, the newness will go away. If things are going well, you'll ease up and become lax. Discipline for journal writing may wane. But stuff is still happening at work, new situations continue to pop up, and little changes (maybe big ones) are taking place. All of this is not to be missed. Trap the details, all the details.

The purpose for doing this

When it comes time to review what you've done for evaluation, resume updating, or applying for a new position, the usefulness of having a record of what you did on this initial job will become crystal clear.

But there's more to the story. Securing and retaining your first reentry job can be an emotional Mount Everest. Journaling can be cathartic and a self-help tool for personal feedback.

To get the most out of it (beyond recording the factual details of what happened), do the following:

• Write your entry for the day (near real-time) soon after your work ends.

• Don't edit as you write; focus on getting this information "out and down."

• Don't edit when you're done - stop, save, and put it away.

• Wait for a few days (a week is good) to review your entries.

You'll sometimes be tempted to erase or rip out an entry, but don't. If you feel differently or have another perspective after reviewing your writing, add a dated comment in the margins.

What you create by doing this will amaze and maybe even astonish you.

I hope that you will make it an unending habit.

Remember, this is your journal. It's for you. Use it to learn, grow, and advance.

Onward!

The Reentry Objective

A few weeks ago, I touched on self-sufficiency in a post on the homelessness case before the Supreme Court. I think a lot about self-sufficiency. It has long seemed like an idea that most people could accept as a universal aspiration for all citizens. Perhaps, most importantly, it is a concept with enough everyday appeal to transcend our polarized social and political climate.

But it's not top-of-mind for most people—which is odd because who wouldn't be for self-sufficiency? Just imagine a country in which every adult was, in fact, an independent, self-sufficient citizen in good standing. Every single one. Imagine.

Suppose that few consider self-sufficiency a terrible idea, and it appeals to people with different political and philosophical persuasions. Why is it so hard for all citizens to achieve it?

I'm sure there are lots of reasons. One certainly involves resources, or rather, how resources are allocated and used. To illustrate this, let's compare for-profit and not-for-profit (NFP) operating models.

For-profit businesses use resources to achieve profitability and create wealth for shareholders through planning and implementation.

The mission is to make money.

Government and NFPs (where reentry initiatives exist) use resources to serve the public good and improve individuals' and communities' quality of life.

The mission is to serve.

Unlike the for-profit world, where profit is the connective tissue, the government and NFP sectors operate differently. These entities don't generate a profit; they must get resources from somewhere else, and strings and restrictions are permanently attached.

A high-level goal, such as self-sufficiency for all, is doomed from the start as too lofty, requiring too much coordination and consensus. Subjugation by program-specific goals and objectives cuts deep at every turn. Each program has its mandated objectives dictated by the administrative and funding source requirements, such as grants, resulting in complex and inefficient Balkanized service systems.

Like all social service categories, reentry programs everywhere must contend with this less-than-optimal landscape, where the resource hunt never stops, and the connective tissue between providers can be tenuous or non-existent.

Nevertheless, reentry programs and business startups are similar. Both start from zero and progress to a goal—for the startup, profitability, and reentry, self-sufficiency. The big difference, of course, is access to resources.

Of course, ours is a capitalistic society that has seen no equal in terms of productivity. However, we struggle with resource allocation, even when the result would benefit our system: fewer dependent citizens and more creators, producers, and consumers.

For social service programs to be more effective and "productive," their goals need universal appeal and buy-in.

Let's focus on self-sufficiency.

Onward!

Reentry Passageways

The Great Recession technically ended in 2009, although the repercussions continued for several years. When I wrote the first draft of “Get Beyond Your Troubled Past” in 2014, this period (the most significant economic downturn since the Great Depression) was still very much on my mind—things were improving steadily; however, the economy and citizenry had been (and remained) unnerved. There were lots of echoes.

Then came 2020 and COVID-19—the economy and the job market were again rocked hard in novel and unexpected ways. Like the Great Recession, many hanging threads remain, and we are still adjusting to the aftermath.

One issue, still under adjustment, is a labor shortage, something we have all experienced in one form or another in our daily lives since the economy re-opened post-Covid.

Take a look at the U.S. Chamber of Commerce chart below. If we stretched it back a few years, an underlying trend would be easier to see: the decline in the U.S. Labor Participation Rate, tracked by the Bureau of Labor Statistics. It stands at 62.5% currently compared to 67.2% in January 2001. The decrease has been anything but orderly, but it’s significant. A drop of 4.7% is a very big deal.

Yes, it’s a boring old BLS statistic, but it has real and important implications for reentering job-seekers. In short, it means lots of job openings!

There are many reasons, including tech innovations, automation, fewer Boomers working, and other generational factors. Hardly a proper reasoning, but we’ll let the economists sort out the “whys.” The net result for most of those reentering (regardless of their personal whys) is an abundance of opportunity compared to the dark days during and after the recession. In short, there are many passageways to getting back in, especially entry-level. Furthermore, the need is great for skilled and semi-skilled workers of nearly all types, either as a starting point (i.e., coming out of a two-year associate’s program, apprenticeships, etc.) or as a promotional step-up from entry-level roles.

The book’s subtitle is “You’re Not Looking for a Job, You’re Looking for a Person.” This refers to the background-challenged worker’s need to make and use personal connections (attained through work) to succeed and progress forward—when, as a challenged job seeker, the digits are rarely your friend. Nothing has changed related to the importance of building relationships and contacts to advance, but the number and range of starting points—the openings—have vastly improved.

As plentiful as the opportunities are now, I must raise the cautionary flag. When passageways abound, people can become lax, sloppy, and lazy. The need to touch all the bases and progress through each stage (as I present in the book and post about here) may seem less pressing and relevant. I know. I see it, have seen it, and I get it.

But my message is this: stay tight and buttoned up, picking and choosing the right entry point and position. Once there, buckle down and stick to your plan. Your goal is to progress, and you do this by putting in the work, logging the time, and building a solid and consistent work history.

The chart features two economic shock events. You don’t see the two similar gut punches that preceded the chart data: the dot.com pop in 1999-2000 and 9/11 in 2001. If you can spot a pattern here, take heed.

Use the many passageways available now to your best advantage, proactively and intentionally, but look beyond this “less difficult” reentry time because it will morph and change, like always.

Onward!

Delivering The Mail

In Get Beyond Your Troubled Past, I introduce the concept of "Delivering the Mail"—strategically sharing your narrative with potential employers. This skill is crucial for any background-challenged job seeker, especially those with felonies.

Why is Delivering the Mail so important? Because when you have a troubled past, your story precedes you. Employers will learn about your background through formal background checks or informal Google searches. If you don't take control of your narrative, someone else will define it for you.

This is where the power of your Personal Narrative comes in. As I discussed in a previous post, crafting your own story is an opportunity to reframe your experiences, highlight your growth, and demonstrate your commitment to a new path. It's a chance to show employers that you are more than your worst mistakes, have learned from your challenges, and are ready to contribute your strengths.

But crafting your narrative is only half the battle. The other half is delivering it effectively, where many job seekers stumble. They overshare, diving into too much detail too soon, or they avoid the subject altogether, hoping their past won't come up.

Neither oversharing nor avoidance is effective. Oversharing can overwhelm or alienate an employer, while avoidance creates an atmosphere of secrecy and mistrust. The key is to be proactive and strategic about when and how you share your story. Take control of the narrative and present yourself in the best light.

Effective Mail Delivery is all about timing. You don't want to lead with your troubled past in your first interaction with a potential employer. Let them get to know your strengths and qualifications first. But you also don't want to wait until late in the hiring process, when an employer might feel blindsided or misled. The key is to find the right moment.

I recommend looking for natural openings to share your narrative. Typically, this comes during the first interview. For example, an employer may ask about a gap in your work history, a straightforward opening for you to present your narrative. However, you may need to proactively interject your narrative if it appears the interview will conclude without a natural opening.

Whenever you deliver your Mail, the key is to do it concisely and authentically. This is where your practiced 3-4 sentence narrative comes in handy.

You might say something like:

"I want to be transparent about my past. I struggled with addiction and incarceration for several years. That experience taught me a lot about personal responsibility. I am healthy and sober now and have been out of the system for 11 months. I'm committed to working hard at building my way back."

Notice how this narrative acknowledges the past but quickly pivots to the lessons learned and the commitment to a different future. It doesn't dwell on details or make excuses, but it also doesn't hide or minimize the reality of the experience.

After delivering your Mail, be prepared for follow-up questions. An employer might ask for more details about your background or how you've changed. Answer honestly but succinctly, always steering the conversation back to your strengths and showing enthusiasm for the opportunity.

Indeed, your primary objective is to proceed deeper into the hiring process and hopefully land the position. But you are also positioning yourself in the eyes of the employer. I have seen situations where an employer cannot hire someone due to company policy. Yet the employer was impressed with how the situation was handled, resulting in the name and phone number of someone who could help.

Delivering the Mail is about owning your story and demonstrating your integrity. It is also a deliberate act designed to maximize your chances of success. Creating your narrative and learning to Deliver the Mail effectively takes work and effort, but rewards await those who learn to do it well.

Onward!

Your Personal Narrative

When reentering the workforce after significant setbacks like incarceration, addiction, or homelessness, one of the most powerful tools in your job search arsenal is your personal narrative - the summary story about how things went the way they did and why you are reentering. This genuine and accurate narrative forms the basis for "Delivering the Mail," a significant tactical step I explain in detail in my book, "Get Beyond Your Troubled Past."

Why is developing your narrative so crucial? First and foremost, it allows you to take control of your story – truthfully and accurately. For many with a criminal record or red-flag gaps in their employment history, the knee-jerk response is to avoid the details (as if they won't come up) or to put a spin on them in some street-esque, self-promotional, BS way.

Not good!

Your narrative is an opportunity to face and reframe your experiences. You get to craft your narrative, where you decide what your story means and where it's heading. Think about it this way: if you don't tell your story, someone else will. And chances are, their version won't be nearly as nuanced, compassionate, or growth-oriented as yours. By proactively sharing your narrative, you avoid any potential negativity or assumptions. You demonstrate that you're not hiding from your past but are willing to own and learn from it.

So, how do you go about developing your narrative? Start by setting aside some quiet, reflective time to write your story from the beginning to where you are now. Don't worry about perfection or polish - focus on getting it all out and down. Be honest about your challenges and setbacks, but don't dwell on them. Acknowledge your choices' impacts, but don't get bogged down in shame or self-blame. Focus on what you've learned, how you've changed, and what drives you now.

When done, set it aside - don't touch it for at least a day; two or three is best. Then, haul it out and cut it in half. If it started as ten pages, make it five, keeping the core events, the meat of the story. Then, set this version aside again for another couple of days.

The last step is another reduction, chopping it into a concise narrative you can share in job search situations. Aim for a brief, 3-4 sentence summary that hits the key points: the issues you've faced, the lessons you've learned, and your commitment to a new path.

For example:

"I faced significant challenges with addiction and incarceration in my past. Through that experience, I learned the importance of personal responsibility, hard work, and surrounding myself with positive influences. I've been sober for a year now and am committed to rebuilding my life and career with integrity and dedication."

Practice delivering your narrative out loud until it feels natural and authentic. Get feedback from trusted mentors or job search coaches. Tweak the language until it feels true to you.

The goal isn't to script a perfect speech but to internalize your story so you can share it with confidence and calm when the opportunity arises. Whether in a job interview, a networking conversation, or a cover letter, your personal narrative is a powerful way to connect with potential employers and demonstrate your resilience and growth.

Getting it out and down where you can read it also allows you to release some of the emotions built up over time and helps clarify the facts. Reading what you write about yourself back to you removes the subconscious storyline you've probably used to support or defend your take on the situation.

Remember, the Marketplace doesn't care how you feel about anything, including your background problem. Consider each prospective employer you meet as a stand-in for the Marketplace. As a result, you need a way to manage your message.

Onward!